Linagliptin (original) (raw)

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Chemical compound

Pharmaceutical compound

Linagliptin
Clinical data
Pronunciation LIN-ə-GLIP-tin
Trade names Tradjenta, Trajenta, Trazenta
Other names BI-1356
AHFS/Drugs.com Monograph
MedlinePlus a611036
License data US DailyMed: Linagliptin
Routes of administration By mouth
ATC code A10BH05 (WHO)
Legal status
Legal status AU: S4 (Prescription only)[1][2] CA: ℞-only[3] UK: POM (Prescription only)[4] US: ℞-only[5] EU: Rx-only[6] In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability ~30% (Tmax = 1.5 hours)
Protein binding 75–99% (concentration-dependent)
Metabolism Minimal (~10% metabolized)
Metabolites Pharmacologically inactive
Elimination half-life ~24 hours
Excretion Feces (80%), urine (5%)[5]
Identifiers
IUPAC name 8-[(3_R_)-3-Aminopiperidin-1-yl]-7-(but-2-yn-1-yl)-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-3,7-dihydro-1_H_-purine-2,6-dione
CAS Number 668270-12-0 checkY
PubChem CID 10096344
IUPHAR/BPS 6318
DrugBank DB08882 checkY
ChemSpider 8271879 ☒N
UNII 3X29ZEJ4R2
KEGG D09566 checkY
ChEBI CHEBI:68610 ☒N
ChEMBL ChEMBL237500 ☒N
CompTox Dashboard (EPA) DTXSID201021653 Edit this at Wikidata
Chemical and physical data
Formula C25H28N8O2
Molar mass 472.553 g·mol−1
3D model (JSmol) Interactive image
Melting point 202 °C (396 °F)
SMILES CC#CCN1C2=C(N=C1N3CCC[C@H](C3)N)N(C(=O)N(C2=O)CC4=NC5=CC=CC=C5C(=N4)C)C
InChI InChI=1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3/t17-/m1/s1 ☒NKey:LTXREWYXXSTFRX-QGZVFWFLSA-N ☒N
☒NcheckY (what is this?) (verify)

Linagliptin, sold under the brand name Tradjenta among others, is a medication used to treat type 2 diabetes (but not type 1) in conjunction with exercise and diet.[7][8] Linagliptin is a dipeptidyl peptidase-4 inhibitor[7] that works by increasing the production of insulin and decreasing the production of glucagon by the pancreas.[7] It is generally less preferred than metformin and sulfonylureas as an initial treatment.[7][9] It is taken by mouth.[7]

Common side effects include inflammation of the nose and throat.[7] Serious side effects may include angioedema, pancreatitis, joint pain.[9][7] Use in pregnancy and breastfeeding is not recommended.[9]

Linagliptin was approved for medical use in the United States,[10] Japan, the European Union, Canada, and Australia in 2011.[7][11] In 2023, it was the 254th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[12][13] From August 2021, linagliptin became available as a generic medicine in the US.[14]

Linagliptin is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes.[5]

Linagliptin may cause severe joint pain.[5][15]

Mechanism of action

[edit]

Linagliptin belongs to a class of drugs called DPP-4 inhibitors.[5]

Linagliptin is the international nonproprietary name (INN).[16] Brand names: Trajenta,[17] Tradjenta.

  1. ^ "Linagliptin, tablet, 5 mg, Trajenta". Pharmaceutical Benefits Scheme (PBS). July 2012. Archived from the original on 31 March 2015. Retrieved 26 September 2014.
  2. ^ "AusPAR: Linagliptin". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 9 April 2023.
  3. ^ "Trajenta Product information". Health Canada. 25 April 2012. Archived from the original on 27 September 2021. Retrieved 3 October 2022.
  4. ^ "Trajenta 5 mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 27 September 2021. Archived from the original on 19 January 2022. Retrieved 3 October 2022.
  5. ^ a b c d e "Tradjenta- linagliptin tablet, film coated". DailyMed. 21 April 2022. Archived from the original on 15 August 2022. Retrieved 3 October 2022.
  6. ^ "Trajenta EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 29 December 2019. Retrieved 11 February 2020.
  7. ^ a b c d e f g h "Linagliptin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 6 April 2019. Retrieved 6 April 2019.
  8. ^ Neumiller JJ (March 2012). "Pharmacology, efficacy, and safety of linagliptin for the treatment of type 2 diabetes mellitus". The Annals of Pharmacotherapy. 46 (3): 358–67. doi:10.1345/aph.1Q522. PMID 22318932. S2CID 207264493.
  9. ^ a b c British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 680. ISBN 9780857113382.
  10. ^ "Drug Approval Package: Tradjenta (linagliptin) Tablets NDA #201280". U.S. Food and Drug Administration (FDA). 7 June 2011. Archived from the original on 3 April 2022. Retrieved 3 October 2022.
  11. ^ "10 years". Boehringer Ingelheim Limited. Archived from the original on 3 October 2022. Retrieved 3 October 2022.
  12. ^ "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  13. ^ "Linagliptin Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  14. ^ "Linagliptin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 25 September 2021. Retrieved 24 September 2021.
  15. ^ "DPP-4 Inhibitors for Type 2 Diabetes: Drug Safety Communication - May Cause Severe Joint Pain". U.S. Food and Drug Administration (FDA). 28 August 2015. Archived from the original on 13 December 2019. Retrieved 1 September 2015.
  16. ^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 61" (PDF). World Health Organization. p. 66. Archived (PDF) from the original on 3 October 2020. Retrieved 10 November 2016.
  17. ^ "Linagliptin: medicine to treat type 2 diabetes". NHS UK. 25 March 2022. Retrieved 21 November 2022.