Lansoprazole (original) (raw)
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Summary
Lansoprazole is a proton pump inhibitor used to help gastrointestinal ulcers heal, to treat symptoms of gastroesophageal reflux disease (GERD), to eradicate Helicobacter pylori, and to treat hypersecretory conditions such as Zollinger-Ellison Syndrome.
Brand Names
Prevacid, Prevpac
Generic Name
Lansoprazole
DrugBank Accession Number
DB00448
Background
Lansoprazole marketed under the brand Prevacid, is a proton pump inhibitor (PPI) and is structurally classified as a substituted benzimidazole.4 It reduces gastric acid secretion by targeting gastric H,K-ATPase pumps and is thus effective at promoting healing in ulcerative diseases, and treating gastroesophageal reflux disease (GERD) along with other pathologies caused by excessive acid secretion.2
Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 369.361
Monoisotopic: 369.075882012
Chemical Formula
C16H14F3N3O2S
Synonyms
- Lansoprazol
- Lansoprazole
- Lansoprazolum
- A 65006
- A-65006
- AG 1749
- AG-1749
Indication
Lansoprazole is used to reduce gastric acid secretion and is approved for short term treatment of active gastric ulcers, active duodenal ulcers, erosive reflux oesophagitis, symptomatic gastroesophageal reflux disease, and non-steroidal anti-inflammatory drug (NSAID) induced gastric and duodenal ulcers. 14Label It may be used in the maintenance and healing of several gastric conditions including duodenal ulcers, NSAID related gastric ulcers, and erosive esophagitis.Label Lansoprazole prevents recurrence of gastric ulcers in patients who have a documented history of gastric ulcers who also use NSAIDs chronically. Label Predictably, it is also useful in the management of hypersecretory conditions including Zollinger-Ellison syndrome. Label Lansoprazole is effective at eradicating H. pylori when used in conjunction with amoxicillin and clarithromycin (triple therapy) or with amoxicillin alone (dual therapy). Label
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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics
Lansoprazole decreases gastric acid secretion by targeting H+,K+-ATPase, which is the enzyme that catalyzes the final step in the acid secretion pathway in parietal cells. 6 Conveniently, lansoprazole administered any time of day is able to inhibit both daytime and nocturnal acid secretion.6 The result is that lansoprazole is effective at healing duodenal ulcers, reduces ulcer-related pain, and offers relief from symptoms of heartburn 6 Lansoprazole also reduces pepsin secretion, making it a useful treatment option for hypersecretory conditions such as Zollinger-Ellison syndrome.76
Mechanism of action
As a PPI, lansoprazole is a prodrug and requires protonation via an acidic environment to become activated. 3 Once protonated, lansoprazole is able to react with cysteine residues, specifically Cys813 and Cys321, on parietal H+,K+-ATPase resulting in stable disulfides.35 PPI's in general are able to provide prolonged inhibition of acid secretion due to their ability to bind covalently to their targets.3
Target | Actions | Organism |
---|---|---|
APotassium-transporting ATPase alpha chain 1 | inhibitor | Humans |
UMicrotubule-associated protein tau | Not Available | Humans |
Absorption
The oral bioavailability of lansoprazole is reported to be 80-90%2 and the peak plasma concentration(Cmax) is achieved about 1.7 hours after oral dosing.Label Food reduces the absorption of lansoprazole (both Cmax and AUC are reduced by 50-70%); therefore, patients should be instructed to take lansoprazole before meals.Label
Volume of distribution
The apparent volume of distribution of lansoprazole is 0.4 L/kg. 3
Protein binding
97% of lansoprazole is plasma protein bound. Label
Metabolism
Lansoprazole is predominantly metabolized in the liver by CYP3A4 and CYP2C19. 3 The resulting major metabolites are 5-hydroxy lansoprazole and the sulfone derivative of lansoprazole. 3Label
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Route of elimination
A reported 14-23% of a lansoprazole is eliminated in the urine with this percentage range including both conjugated and unconjugated hydroxylated metabolites. 6
Half-life
One source reports the half life of lansoprazole to be 0.9 - 1.6 hours2, while another source cites 0.9 - 2.1 hours3. The general consensus is that lansoprazole has a short half life and is approximately 2 hours or less. Label These numbers may be misleading since it suggests that lansoprazole has a short duration of action when in practice, lansoprazole can effectively inhibit acid secretion for ~24 hours due to it's mechanism of action. Label
Clearance
The reported clearance of lansoprazole is 400-650 mL/min. 3
Adverse Effects
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Toxicity
The most commonly reported adverse events occurring more frequently in lansoprazole treated patients compared to placebo include abdominal pain, constipation, diarrhea, and nausea.Label There is a case report of toxic epidermal necrolysis (TEN), which is a rare but very serious cutaneous reaction, caused by lansoprazole.8 The previously healthy patient presented with symptoms of TEN 15 days after starting lansoprazole to manage peptic disease.8 Although the use of PPI's is rarely associated with TEN, causation should be considered if a patient presents with TEN shortly after newly commencing a PPI.8
In a single case report, a patient ingested 600 mg of lansoprazole and did not experience any adverse effects or symptoms of overdose.Label Overall, lansoprazole is well tolerated with relatively few adverse effects.
Lansoprazole is classified as Pregnancy Category B.Label Although there are animal studies that suggest lansoprazole does not cause harm to the fetus, there is still a paucity of human data. Hence, lansoprazole should only be administered to pregnant women if other options with more safety data have been exhausted.
It is unknown if lansoprazole is excreted in human breast milk.Label It is worth mentioning that lansoprazole has been used safely in infants, and is therefore likely safe to use during breastfeeding.9
Pathways
Pathway | Category |
---|---|
Lansoprazole Metabolism Pathway | Drug metabolism |
Lansoprazole Action Pathway | Drug action |
Interacting Gene/Enzyme | Allele name | Genotype(s) | Defining Change(s) | Type(s) | Description | Details |
---|---|---|---|---|---|---|
Cytochrome P450 2C19 | CYP2C19*2 | (A;A) | A Allele, homozygote | Effect Directly Studied | Patients with this genotype have reduced metabolism of lansoprazole. | Details |
Cytochrome P450 2C19 | CYP2C19*3 | (A;A) | A Allele, homozygote | Effect Directly Studied | Patients with this genotype have reduced metabolism of lansoprazole. | Details |
Multidrug resistance protein 1 | --- | (C;T) | C Allele, heterozygote | Effect Directly Studied | Patients with this genotype have increased plasma concentration of lansoprazole. | Details |
Cytochrome P450 2C19 | CYP2C19*2A | Not Available | 681G>A | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*2B | Not Available | 681G>A | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*4 | Not Available | 1A>G | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*5 | Not Available | 1297C>T | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*6 | Not Available | 395G>A | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*7 | Not Available | 19294T>A | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*22 | Not Available | 557G>C / 991A>G | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*24 | Not Available | 99C>T / 991A>G … show all | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
Cytochrome P450 2C19 | CYP2C19*35 | Not Available | 12662A>G | Effect Inferred | Poor metabolizer, lower dose requirement, improved drug efficacy | Details |
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug | Interaction |
---|---|
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Abametapir | The serum concentration of Lansoprazole can be increased when it is combined with Abametapir. |
Abatacept | The metabolism of Lansoprazole can be increased when combined with Abatacept. |
Abemaciclib | Lansoprazole may decrease the excretion rate of Abemaciclib which could result in a higher serum level. |
Abiraterone | The metabolism of Lansoprazole can be decreased when combined with Abiraterone. |
Abrocitinib | The metabolism of Abrocitinib can be decreased when combined with Lansoprazole. |
Food Interactions
- Take before a meal. Take 30-60 minutes before meals.
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Product Images
International/Other Brands
Agopton (Takeda) / Bamalite / Lansoloc (Cipla Medpro) / Lanzol (Cipla) / Lanzopral (Pharma Investi) / Lanzopran (Ranbaxy) / Limpidex (Sigma-Tau) / Monolitum (Salvat) / Ogast (Takeda) / Ogastro (Abbott) / Opiren (Almirall) / Prevacid 24HR (Novartis) / Prosogan (Takeda) / Takepron (Takeda) / Ulpax (Hormona) / Zoprol (Toprak) / Zoton (Pfizer)
Brand Name Prescription Products
Generic Prescription Products
Over the Counter Products
Mixture Products
ATC Codes
- A02BC — Proton pump inhibitors
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM A02BD02 — Lansoprazole, tetracycline and metronidazole
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM A02BD07 — Lansoprazole, amoxicillin and clarithromycin
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM A02BD09 — Lansoprazole, clarithromycin and tinidazole
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM A02BD10 — Lansoprazole, amoxicillin and levofloxacin
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM A02BD03 — Lansoprazole, amoxicillin and metronidazole
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM A02BC53 — Lansoprazole, combinations
- A02BC — Proton pump inhibitors
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
Drug Categories
- Acid Reducers
- Alimentary Tract and Metabolism
- Anti-Ulcer Agents
- BCRP/ABCG2 Inhibitors
- Benzimidazoles
- Cytochrome P-450 CYP2C18 Substrates
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (strong)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Gastric Acid Lowering Agents
- Gastrointestinal Agents
- Heterocyclic Compounds, Fused-Ring
- Inhibition Gastric Acid Secretion
- OAT3/SLC22A8 Inhibitors
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Proton Pump Inhibitors
- Proton-pump Inhibitors
- Pyridines
- Sulfoxides
- Sulfur Compounds
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Kingdom
Super Class
Class
Sub Class
Direct Parent
Alternative Parents
Methylpyridines / Alkyl aryl ethers / Benzenoids / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Organic oxides / Hydrocarbon derivatives / Alkyl fluorides show 4 more
Substituents
Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Methylpyridine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organofluoride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound / Pyridine / Sulfinyl compound / Sulfinylbenzimidazole / Sulfoxide show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfoxide, pyridines, benzimidazoles (CHEBI:6375)
Affected organisms
- Humans and other mammals
UNII
CAS number
103577-45-3
InChI Key
MJIHNNLFOKEZEW-UHFFFAOYSA-N
InChI
InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
IUPAC Name
2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
SMILES
CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1
Synthesis Reference
Clarke Slemon, Bob Macel, "Preparation of omeprazole and lansoprazole." U.S. Patent US5374730, issued December, 1986.
General References
- Matheson AJ, Jarvis B: Lansoprazole: an update of its place in the management of acid-related disorders. Drugs. 2001;61(12):1801-33. [Article]
- Shin JM, Sachs G: Pharmacology of proton pump inhibitors. Curr Gastroenterol Rep. 2008 Dec;10(6):528-34. [Article]
- Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [Article]
- Gremse DA: Lansoprazole: pharmacokinetics, pharmacodynamics and clinical uses. Expert Opin Pharmacother. 2001 Oct;2(10):1663-70. doi: 10.1517/14656566.2.10.1663 . [Article]
- Bosnjak T, Solberg R, Hemati PD, Jafari A, Kassem M, Johansen HT: Lansoprazole inhibits the cysteine protease legumain by binding to the active site. Basic Clin Pharmacol Toxicol. 2019 Mar 27. doi: 10.1111/bcpt.13230. [Article]
- Barradell LB, Faulds D, McTavish D: Lansoprazole. A review of its pharmacodynamic and pharmacokinetic properties and its therapeutic efficacy in acid-related disorders. Drugs. 1992 Aug;44(2):225-50. doi: 10.2165/00003495-199244020-00007. [Article]
- Hirschowitz BI, Simmons JL, Johnson LF, Mohnen J: Risk factors for esophagitis in extreme acid hypersecretors with and without Zollinger-Ellison syndrome. Clin Gastroenterol Hepatol. 2004 Mar;2(3):220-9. [Article]
- Fracaroli TS, Miranda LQ, Sodre JL, Chaves M, Gripp A: Toxic epidermal necrolysis induced by lansoprazole. An Bras Dermatol. 2013 Jan-Feb;88(1):117-20. [Article]
- Lansoprazole - Drugs and Lactation Database [Link]
- FDA Approved Drug Products: Prevacid (lansoprazole) [Link]
External Links
Human Metabolome Database
KEGG Drug
PubChem Compound
PubChem Substance
ChemSpider
BindingDB
RxNav
ChEBI
ChEMBL
Therapeutic Targets Database
PharmGKB
RxList
Drugs.com
Wikipedia
FDA label
Clinical Trials
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Manufacturers
- Matrix laboratories ltd
- Teva pharmaceuticals usa
- Takeda pharmaceuticals north america inc
- Novartis consumer health inc
- Sandoz inc
Packagers
- Abbott Laboratories Ltd.
- Advanced Pharmaceutical Services Inc.
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Cardinal Health
- Caremark LLC
- Direct Pharmaceuticals Inc.
- Dispensing Solutions
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Innoviant Pharmacy Inc.
- Inventia Healthcare Pvt Ltd.
- Lake Erie Medical and Surgical Supply
- Mckesson Corp.
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Novartis AG
- Nucare Pharmaceuticals Inc.
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Promex Medical Inc.
- Redpharm Drug
- Resource Optimization and Innovation LLC
- Sandoz
- Southwood Pharmaceuticals
- Stat Rx Usa
- Takeda Pharmaceutical Co. Ltd.
- TAP Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Va Cmop Dallas
- Vangard Labs Inc.
Dosage Forms
Form | Route | Strength |
---|---|---|
Capsule | Oral | |
Capsule | Oral | 30.000 mg |
Capsule | Oral | 15.000 mg |
Capsule, coated pellets | Oral | |
Kit | Not applicable | 0.9 g/0.9g |
Tablet | Oral | |
Capsule | Oral | |
Capsule, extended release | Oral | 15 mg |
Capsule, extended release | Oral | 30 mg |
Capsule, coated pellets | Oral | 30 mg |
Capsule, coated | Oral | 30 mg |
Capsule, delayed release | Oral | |
Capsule | Oral | 15 mg/1 |
Capsule, delayed release | Oral | 15 mg/1 |
Capsule, delayed release | Oral | 344.83 mg |
Capsule, delayed release | Oral | 353 mg |
Capsule, delayed release pellets | Oral | 15 mg/1 |
Capsule, delayed release pellets | Oral | 30 mg/1 |
Powder | Not applicable | 1 g/1g |
Tablet, orally disintegrating, delayed release | Oral | 30 mg/1 |
Capsule; capsule, delayed release; kit; tablet | Oral | |
Capsule, delayed release | Oral | 15 MG |
Tablet, orally disintegrating | Oral | |
Capsule, delayed release | Oral | 30 mg |
Capsule | Oral | 15 MG |
Capsule | Oral | 30 MG |
Capsule, coated | Oral | 3000000 mg |
Capsule; capsule, delayed release | Oral | 30 mg |
Capsule, coated pellets | Oral | 15 mg |
Tablet, coated | Oral | 15 mg |
Capsule, coated | Oral | 15 mg |
Capsule, extended release | Oral | |
Capsule | Oral | 30.0 mg |
Tablet, soluble | Oral | 30 mg |
Injection, powder, for solution; injection, powder, lyophilized, for solution | Intravenous | 30 mg |
Capsule, delayed release | Oral | 30 mg/1 |
Injection | Intravenous | 30 mg/5mL |
Suspension | Oral | 15 mg/1 |
Suspension | Oral | 30 mg/1 |
Tablet, orally disintegrating | Oral | 15 mg/1 |
Tablet, orally disintegrating | Oral | 30 mg/1 |
Tablet, orally disintegrating, delayed release | Oral | 15 mg/1 |
Tablet, delayed release | Oral | 15 mg |
Tablet, delayed release | Oral | 30 mg |
Injection, powder, for solution | Intravenous | 30 mg/5mL |
Kit | Oral | |
Injection, powder, for solution | Intravenous | 30 mg |
Tablet; tablet, delayed release | Oral | 15 MG |
Tablet; tablet, delayed release | Oral | 30 MG |
Capsule; tablet | Oral | |
Powder | 30 mg/1vial | |
Tablet | Oral | 15 mg |
Tablet, orally disintegrating | Oral | 15 mg |
Tablet | Oral | 30 mg |
Tablet, orally disintegrating | Oral | 30 mg |
Prices
Unit description | Cost | Unit |
---|---|---|
Prevacid SoluTab 100 15 mg Dispersible Tablet Box | 620.65USD | box |
Prevacid NapraPAC 84 15-500 mg Kit Box | 175.8USD | box |
Prevpac Miscellaneous | 32.02USD | ea |
Prevpac patient pack | 28.22USD | each |
Lansoprazole 100% powder | 27.54USD | g |
Prevacid iv 30 mg vial | 27.31USD | vial |
Prevacid dr 15 mg capsule | 6.25USD | capsule |
Prevacid SoluTab 30 mg Dispersible Tablet | 6.21USD | dispersible tablet |
Prevacid 15 mg capsule dr | 6.0USD | capsule |
Prevacid 30 mg capsule dr | 6.0USD | capsule |
Prevacid dr 30 mg capsule | 5.91USD | capsule |
Lansoprazole 15 mg Delayed Release Capsule | 5.9USD | capsule |
Lansoprazole 30 mg Delayed Release Capsule | 5.9USD | capsule |
Prevacid 15 mg solutab | 5.73USD | tablet |
Prevacid 30 mg solutab | 5.73USD | tablet |
Lansoprazole dr 15 mg capsule | 5.67USD | capsule |
Lansoprazole dr 30 mg capsule | 5.67USD | capsule |
Prevacid 30 mg Delayed Release Capsule | 4.45USD | capsule |
Prevacid 15 mg Delayed Release Capsule | 4.32USD | capsule |
Apo-Lansoprazole 15 mg Delayed Release Capsule | 1.17USD | capsule |
Apo-Lansoprazole 30 mg Delayed Release Capsule | 1.17USD | capsule |
Novo-Lansoprazole 15 mg Delayed Release Capsule | 1.17USD | capsule |
Novo-Lansoprazole 30 mg Delayed Release Capsule | 1.17USD | capsule |
Prevacid 24hr dr 15 mg capsule | 0.86USD | capsule |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent Number | Pediatric Extension | Approved | Expires (estimated) | Region |
---|---|---|---|---|
US4628098 | No | 1986-12-09 | 2009-11-10 | |
CA2419067 | No | 2008-12-23 | 2021-08-17 | |
CA1327010 | No | 1994-02-15 | 2011-02-15 | |
US7399485 | Yes | 2008-07-15 | 2018-11-26 | |
US6328994 | Yes | 2001-12-11 | 2019-11-17 | |
US7875292 | Yes | 2011-01-25 | 2019-11-17 | |
US7431942 | Yes | 2008-10-07 | 2019-11-17 | |
US7396841 | Yes | 2008-07-08 | 2022-02-17 | |
US9901546 | Yes | 2018-02-27 | 2019-11-17 | |
US11077055 | No | 2021-08-03 | 2036-04-21 | |
US11986554 | No | 2016-04-21 | 2036-04-21 |
State
Solid
Experimental Properties
Property | Value | Source |
---|---|---|
melting point (°C) | 178-182 °C | https://www.chemicalbook.com/ChemicalProductProperty\_US\_CB6396972.aspx |
water solubility | 0.97 mg/L | FDA Label |
Predicted Properties
Property | Value | Source |
---|---|---|
Water Solubility | 0.25 mg/mL | ALOGPS |
logP | 2.84 | ALOGPS |
logP | 3.03 | Chemaxon |
logS | -3.2 | ALOGPS |
pKa (Strongest Acidic) | 9.35 | Chemaxon |
pKa (Strongest Basic) | 4.16 | Chemaxon |
Physiological Charge | 0 | Chemaxon |
Hydrogen Acceptor Count | 4 | Chemaxon |
Hydrogen Donor Count | 1 | Chemaxon |
Polar Surface Area | 67.87 Å2 | Chemaxon |
Rotatable Bond Count | 6 | Chemaxon |
Refractivity | 87.61 m3·mol-1 | Chemaxon |
Polarizability | 34.59 Å3 | Chemaxon |
Number of Rings | 3 | Chemaxon |
Bioavailability | 1 | Chemaxon |
Rule of Five | Yes | Chemaxon |
Ghose Filter | Yes | Chemaxon |
Veber's Rule | No | Chemaxon |
MDDR-like Rule | Yes | Chemaxon |
Predicted ADMET Features
Property | Value | Probability |
---|---|---|
Human Intestinal Absorption | + | 0.9972 |
Blood Brain Barrier | + | 0.7007 |
Caco-2 permeable | + | 0.8866 |
P-glycoprotein substrate | Non-substrate | 0.547 |
P-glycoprotein inhibitor I | Inhibitor | 0.5357 |
P-glycoprotein inhibitor II | Non-inhibitor | 0.8692 |
Renal organic cation transporter | Inhibitor | 0.5521 |
CYP450 2C9 substrate | Non-substrate | 0.7826 |
CYP450 2D6 substrate | Non-substrate | 0.8659 |
CYP450 3A4 substrate | Substrate | 0.6771 |
CYP450 1A2 substrate | Inhibitor | 0.9106 |
CYP450 2C9 inhibitor | Non-inhibitor | 0.9071 |
CYP450 2D6 inhibitor | Inhibitor | 0.8932 |
CYP450 2C19 inhibitor | Inhibitor | 0.8993 |
CYP450 3A4 inhibitor | Inhibitor | 0.7959 |
CYP450 inhibitory promiscuity | High CYP Inhibitory Promiscuity | 0.8768 |
Ames test | Non AMES toxic | 0.5858 |
Carcinogenicity | Non-carcinogens | 0.7944 |
Biodegradation | Not ready biodegradable | 1.0 |
Rat acute toxicity | 1.8997 LD50, mol/kg | Not applicable |
hERG inhibition (predictor I) | Weak inhibitor | 0.8777 |
hERG inhibition (predictor II) | Non-inhibitor | 0.8734 |
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)
Mass Spec (NIST)
Not Available
Spectra
Chromatographic Properties
Collision Cross Sections (CCS)
Adduct | CCS Value (Å2) | Source type | Source |
---|---|---|---|
[M-H]- | 190.7522069 | predicted | DarkChem Lite v0.1.0 |
[M-H]- | 173.57635 | predicted | DeepCCS 1.0 (2019) |
[M+H]+ | 191.5039069 | predicted | DarkChem Lite v0.1.0 |
[M+H]+ | 175.93436 | predicted | DeepCCS 1.0 (2019) |
[M+Na]+ | 191.3743069 | predicted | DarkChem Lite v0.1.0 |
[M+Na]+ | 182.0275 | predicted | DeepCCS 1.0 (2019) |
Targets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
The catalytic subunit of the gastric H(+)/K(+) ATPase pump which transports H(+) ions in exchange for K(+) ions across the apical membrane of parietal cells. Uses ATP as an energy source to pump H(+) ions to the gastric lumen while transporting K(+) ion from the lumen into the cell (By similarity). Remarkably generates a million-fold proton gradient across the gastric parietal cell membrane, acidifying the gastric juice down to pH 1 (By similarity). Within a transport cycle, the transfer of a H(+) ion across the membrane is coupled to ATP hydrolysis and is associated with a transient phosphorylation that shifts the pump conformation from inward-facing (E1) to outward-facing state (E2). The release of the H(+) ion in the stomach lumen is followed by binding of K(+) ion converting the pump conformation back to the E1 state (By similarity).
Specific Function
ATP binding
Gene Name
ATP4A
Uniprot ID
Uniprot Name
Potassium-transporting ATPase alpha chain 1
Molecular Weight
114117.74 Da
References
- Matheson AJ, Jarvis B: Lansoprazole: an update of its place in the management of acid-related disorders. Drugs. 2001;61(12):1801-33. [Article]
- Langtry HD, Wilde MI: Lansoprazole. An update of its pharmacological properties and clinical efficacy in the management of acid-related disorders. Drugs. 1997 Sep;54(3):473-500. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Promotes microtubule assembly and stability, and might be involved in the establishment and maintenance of neuronal polarity (PubMed:21985311). The C-terminus binds axonal microtubules while the N-terminus binds neural plasma membrane components, suggesting that tau functions as a linker protein between both (PubMed:21985311, PubMed:32961270). Axonal polarity is predetermined by TAU/MAPT localization (in the neuronal cell) in the domain of the cell body defined by the centrosome. The short isoforms allow plasticity of the cytoskeleton whereas the longer isoforms may preferentially play a role in its stabilization.
Specific Function
actin binding
Gene Name
MAPT
Uniprot ID
Uniprot Name
Microtubule-associated protein tau
Molecular Weight
78927.025 Da
References
- Rojo LE, Alzate-Morales J, Saavedra IN, Davies P, Maccioni RB: Selective interaction of lansoprazole and astemizole with tau polymers: potential new clinical use in diagnosis of Alzheimer's disease. J Alzheimers Dis. 2010;19(2):573-89. doi: 10.3233/JAD-2010-1262. [Article]
Enzymes
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195).
Specific Function
arachidonic acid monooxygenase activity
Gene Name
CYP1A1
Uniprot ID
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
- Curi-Pedrosa R, Daujat M, Pichard L, Ourlin JC, Clair P, Gervot L, Lesca P, Domergue J, Joyeux H, Fourtanier G, et al.: Omeprazole and lansoprazole are mixed inducers of CYP1A and CYP3A in human hepatocytes in primary culture. J Pharmacol Exp Ther. 1994 Apr;269(1):384-92. [Article]
- Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity).
Specific Function
aromatase activity
Gene Name
CYP1B1
Uniprot ID
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
- Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Very minor contribution to metabolism and not relevant at therapeutic concentrations.
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316).
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2C8
Uniprot ID
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
- Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A: Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. [Article]
- Pichard L, Curi-Pedrosa R, Bonfils C, Jacqz-Aigrain E, Domergue J, Joyeux H, Cosme J, Guengerich FP, Maurel P: Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Pharmacol. 1995 Feb;47(2):410-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Very minor contribution to metabolism and not relevant at therapeutic concentrations. R-lansoprazole acts as a steroespecific inducer of the enzyme but the degree of activation varies depending on the substrate. All data supporting this enzyme action are in vitro,
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031).
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C9
Uniprot ID
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Liu KH, Kim MJ, Jung WM, Kang W, Cha IJ, Shin JG: Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner. Drug Metab Dispos. 2005 Feb;33(2):209-13. doi: 10.1124/dmd.104.001438. Epub 2004 Nov 10. [Article]
- Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [Article]
- Liu KH, Kim MJ, Shon JH, Moon YS, Seol SY, Kang W, Cha IJ, Shin JG: Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro. Xenobiotica. 2005 Jan;35(1):27-38. doi: 10.1080/00498250400026472 . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in retinoid metabolism. Hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may modulate atRA signaling and clearance. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2C18
Uniprot ID
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
- Pichard L, Curi-Pedrosa R, Bonfils C, Jacqz-Aigrain E, Domergue J, Joyeux H, Cosme J, Guengerich FP, Maurel P: Oxidative metabolism of lansoprazole by human liver cytochromes P450. Mol Pharmacol. 1995 Feb;47(2):410-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2D6
Uniprot ID
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
- Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981).
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
- Kim KA, Kim MJ, Park JY, Shon JH, Yoon YR, Lee SS, Liu KH, Chun JH, Hyun MH, Shin JG: Stereoselective metabolism of lansoprazole by human liver cytochrome P450 enzymes. Drug Metab Dispos. 2003 Oct;31(10):1227-34. doi: 10.1124/dmd.31.10.1227. [Article]
- Curi-Pedrosa R, Daujat M, Pichard L, Ourlin JC, Clair P, Gervot L, Lesca P, Domergue J, Joyeux H, Fourtanier G, et al.: Omeprazole and lansoprazole are mixed inducers of CYP1A and CYP3A in human hepatocytes in primary culture. J Pharmacol Exp Ther. 1994 Apr;269(1):384-92. [Article]
- Masubuchi N, Li AP, Okazaki O: An evaluation of the cytochrome P450 induction potential of pantoprazole in primary human hepatocytes. Chem Biol Interact. 1998 Jul 3;114(1-2):1-13. [Article]
- Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A: Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. [Article]
- Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Higher affinity for S-lansoprazole but contributes to the metabolism of R-lansoprazole as well. This affinity is also proportional to the potency of each molecule as an inhibitor of the enzyme.
General Function
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307).
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
- Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A: Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. [Article]
- Kim KA, Kim MJ, Park JY, Shon JH, Yoon YR, Lee SS, Liu KH, Chun JH, Hyun MH, Shin JG: Stereoselective metabolism of lansoprazole by human liver cytochrome P450 enzymes. Drug Metab Dispos. 2003 Oct;31(10):1227-34. doi: 10.1124/dmd.31.10.1227. [Article]
- Liu KH, Kim MJ, Shon JH, Moon YS, Seol SY, Kang W, Cha IJ, Shin JG: Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro. Xenobiotica. 2005 Jan;35(1):27-38. doi: 10.1080/00498250400026472 . [Article]
- Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [Article]
- Kita T, Sakaeda T, Baba T, Aoyama N, Kakumoto M, Kurimoto Y, Kawahara Y, Okamura N, Kirita S, Kasuga M, Okumura K: Different contribution of CYP2C19 in the in vitro metabolism of three proton pump inhibitors. Biol Pharm Bull. 2003 Mar;26(3):386-90. [Article]
- Yasui-Furukori N, Saito M, Uno T, Takahata T, Sugawara K, Tateishi T: Effects of fluvoxamine on lansoprazole pharmacokinetics in relation to CYP2C19 genotypes. J Clin Pharmacol. 2004 Nov;44(11):1223-9. doi: 10.1177/0091270004269015. [Article]
- Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [Article]
- Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [Article]
- Flockhart Table of Drug Interactions [Link]
Transporters
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity).
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCG2
Uniprot ID
Uniprot Name
Broad substrate specificity ATP-binding cassette transporter ABCG2
Molecular Weight
72313.47 Da
References
- Suzuki K, Doki K, Homma M, Tamaki H, Hori S, Ohtani H, Sawada Y, Kohda Y: Co-administration of proton pump inhibitors delays elimination of plasma methotrexate in high-dose methotrexate therapy. Br J Clin Pharmacol. 2009 Jan;67(1):44-9. doi: 10.1111/j.1365-2125.2008.03303.x. Epub 2008 Nov 17. [Article]
- Delayed Elimination of Methotrexate Associated with Co-Administration of Proton Pump Inhibitors [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218).
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
Uniprot Name
ATP-dependent translocase ABCB1
Molecular Weight
141477.255 Da
References
- Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [Article]
- Kodaira C, Sugimoto M, Nishino M, Yamade M, Shirai N, Uchida S, Ikuma M, Yamada S, Watanabe H, Hishida A, Furuta T: Effect of MDR1 C3435T polymorphism on lansoprazole in healthy Japanese subjects. Eur J Clin Pharmacol. 2009 Jun;65(6):593-600. doi: 10.1007/s00228-009-0625-8. Epub 2009 Feb 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity).
Specific Function
organic anion transmembrane transporter activity
Gene Name
SLC22A8
Uniprot ID
Uniprot Name
Organic anion transporter 3
Molecular Weight
59855.585 Da
References
- Hamada Y, Ikemura K, Iwamoto T, Okuda M: Stereoselective Inhibition of Renal Basolateral Human Organic Anion Transporter 3 by Lansoprazole Enantiomers. Pharmacology. 2018;101(3-4):176-183. doi: 10.1159/000485920. Epub 2018 Jan 19. [Article]
- Proton Pump Inhibitors Inhibit Methotrexate Transport by Renal Basolateral Organic Anion Transporter hOAT3 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:11388889, PubMed:11408531, PubMed:12439218, PubMed:12719534, PubMed:15389554, PubMed:16263091, PubMed:16272756, PubMed:16581093, PubMed:19536068, PubMed:21128598, PubMed:23680637, PubMed:24961373, PubMed:34040533, PubMed:9187257, PubMed:9260930, PubMed:9655880). Functions as a pH- and Na(+)-independent, bidirectional transporter (By similarity). Cation cellular uptake or release is driven by the electrochemical potential (i.e. membrane potential and concentration gradient) and substrate selectivity (By similarity). Hydrophobicity is a major requirement for recognition in polyvalent substrates and inhibitors (By similarity). Primarily expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (By similarity). Most likely functions as an uptake carrier in enterocytes contributing to the intestinal elimination of organic cations from the systemic circulation (PubMed:16263091). Transports endogenous monoamines such as N-1-methylnicotinamide (NMN), guanidine, histamine, neurotransmitters dopamine, serotonin and adrenaline (PubMed:12439218, PubMed:24961373, PubMed:35469921, PubMed:9260930). Also transports natural polyamines such as spermidine, agmatine and putrescine at low affinity, but relatively high turnover (PubMed:21128598). Involved in the hepatic uptake of vitamin B1/thiamine, hence regulating hepatic lipid and energy metabolism (PubMed:24961373). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with lower efficency (PubMed:17460754). Also capable of transporting non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). May contribute to the transport of cationic compounds in testes across the blood-testis-barrier (Probable). Also involved in the uptake of xenobiotics tributylmethylammonium (TBuMA), quinidine, N-methyl-quinine (NMQ), N-methyl-quinidine (NMQD) N-(4,4-azo-n-pentyl)-quinuclidine (APQ), azidoprocainamide methoiodide (AMP), N-(4,4-azo-n-pentyl)-21-deoxyajmalinium (APDA) and 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:11408531, PubMed:15389554, PubMed:35469921, PubMed:9260930).
Specific Function
(R)-carnitine transmembrane transporter activity
Gene Name
SLC22A1
Uniprot ID
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
- Nies AT, Hofmann U, Resch C, Schaeffeler E, Rius M, Schwab M: Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs). PLoS One. 2011;6(7):e22163. doi: 10.1371/journal.pone.0022163. Epub 2011 Jul 14. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:9260930, PubMed:9687576). Functions as a Na(+)-independent, bidirectional uniporter (PubMed:21128598, PubMed:9687576). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:15212162, PubMed:9260930, PubMed:9687576). However, may also engage electroneutral cation exchange when saturating concentrations of cation substrates are reached (By similarity). Predominantly expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (PubMed:15783073). Implicated in monoamine neurotransmitters uptake such as histamine, dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, serotonin and tyramine, thereby supporting a physiological role in the central nervous system by regulating interstitial concentrations of neurotransmitters (PubMed:16581093, PubMed:17460754, PubMed:9687576). Also capable of transporting dopaminergic neuromodulators cyclo(his-pro), salsolinol and N-methyl-salsolinol, thereby involved in the maintenance of dopaminergic cell integrity in the central nervous system (PubMed:17460754). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Also transports guanidine and endogenous monoamines such as vitamin B1/thiamine, creatinine and N-1-methylnicotinamide (NMN) (PubMed:12089365, PubMed:15212162, PubMed:17072098, PubMed:24961373, PubMed:9260930). Mediates the uptake and efflux of quaternary ammonium compound choline (PubMed:9260930). Mediates the bidirectional transport of polyamine agmatine and the uptake of polyamines putrescine and spermidine (PubMed:12538837, PubMed:21128598). Able to transport non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). Also involved in the uptake of xenobiotic 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:12395288, PubMed:16394027). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable).
Specific Function
acetylcholine transmembrane transporter activity
Gene Name
SLC22A2
Uniprot ID
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
- Nies AT, Hofmann U, Resch C, Schaeffeler E, Rius M, Schwab M: Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs). PLoS One. 2011;6(7):e22163. doi: 10.1371/journal.pone.0022163. Epub 2011 Jul 14. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:10196521, PubMed:10966924, PubMed:12538837, PubMed:17460754, PubMed:20858707). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:10966924). Functions as a Na(+)- and Cl(-)-independent, bidirectional uniporter (PubMed:12538837). Implicated in monoamine neurotransmitters uptake such as dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, histamine, serotonin and tyramine, thereby supporting a role in homeostatic regulation of aminergic neurotransmission in the brain (PubMed:10196521, PubMed:16581093, PubMed:20858707). Transports dopaminergic neuromodulators cyclo(his-pro) and salsolinol with low efficiency (PubMed:17460754). May be involved in the uptake and disposition of cationic compounds by renal clearance from the blood flow (PubMed:10966924). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (Probable). Mediates the transport of polyamine spermidine and putrescine (By similarity). Mediates the bidirectional transport of polyamine agmatine (PubMed:12538837). Also transports guanidine (PubMed:10966924). May also mediate intracellular transport of organic cations, thereby playing a role in amine metabolism and intracellular signaling (By similarity).
Specific Function
monoamine transmembrane transporter activity
Gene Name
SLC22A3
Uniprot ID
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
- Nies AT, Hofmann U, Resch C, Schaeffeler E, Rius M, Schwab M: Proton pump inhibitors inhibit metformin uptake by organic cation transporters (OCTs). PLoS One. 2011;6(7):e22163. doi: 10.1371/journal.pone.0022163. Epub 2011 Jul 14. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 01, 2024 12:45