Butalbital (original) (raw)

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Barbiturate drug used for headaches

Pharmaceutical compound

Butalbital
Clinical data
Other names 5-allyl-5-isobutylbarbituric acid
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601009
Routes of administration By mouth
Drug class Barbiturate
ATC code none
Legal status
Legal status BR: Class B1 (Psychoactive drugs)[1] CA: Schedule IV DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule III UN: Psychotropic Schedule III
Pharmacokinetic data
Bioavailability 20-45%
Metabolism Liver mainly CYP3A4
Elimination half-life 35 hours[2]
Excretion Kidney
Identifiers
IUPAC name 5-(2-Methylpropyl)-5-(2-propenyl)-2,4,6(1_H_,3_H_,5_H_)-pyrimidinetrione
CAS Number 77-26-9 checkY
PubChem CID 2481
IUPHAR/BPS 7138
DrugBank DB00241 checkY
ChemSpider 2387 checkY
UNII KHS0AZ4JVK
KEGG D03182 checkY
ChEBI CHEBI:102524 checkY
ChEMBL ChEMBL454 checkY
CompTox Dashboard (EPA) DTXSID6022711 Edit this at Wikidata
ECHA InfoCard 100.000.926 Edit this at Wikidata
Chemical and physical data
Formula C11H16N2O3
Molar mass 224.260 g·mol−1
3D model (JSmol) Interactive image
SMILES O=C1NC(=O)NC(=O)C1(CC(C)C)C\C=C
InChI InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16) checkYKey:UZVHFVZFNXBMQJ-UHFFFAOYSA-N checkY
(verify)

Butalbital is a barbiturate with an intermediate duration of action. Butalbital is often combined with other medications, such as paracetamol (acetaminophen) (as butalbital/acetaminophen) or aspirin, for the treatment of pain and headache. The various formulations combined with codeine are FDA-approved for the treatment of tension headaches. Butalbital has the same chemical formula as talbutal but a different structure—one that presents as 5-allyl-5-isobutylbarbituric acid.[3]

Combinations include:[_citation needed_]

There are specific treatments which are appropriate for targeting migraines and headaches.[4] Butalbital is not recommended as a first-line treatment because it impairs alertness, brings risk of dependence and addiction, and increases the risk that episodic headaches will become chronic.[5] When other treatments are unavailable or ineffective, butalbital may be appropriate if the patient can be monitored to prevent the development of chronic headache.[5]

Side effects for butalbital is usually well tolerated. Commonly reported side effects for butalbital, some of which tend to subside with continued use, include:[_citation needed_]

Rare side effects include Stevens–Johnson syndrome, an adverse reaction to barbiturates, and anaphylaxis.

The risk and severity of all side effects is greatly increased when butalbital are combined with other sedatives (e.g., alcohol, opioids, benzodiazepines, antihistamines). Butalbital when taken with sedatives can cause life-threatening respiratory depression and death. Inhibitors of the hepatic enzyme CYP3A4 may also increase the risk, severity, and duration of side effects, many drugs inhibit this enzyme as do some foods such as grapefruit and the blood orange.[_citation needed_]

Butalbital can cause dependence or addiction.[_citation needed_]

Mixing with alcohol, benzodiazepines, and other depressants increases the risk of intoxication, increases respiratory depression, and increases liver toxicity when in combination with paracetamol (acetaminophen). Use of butalbital and alcohol, benzodiazepines, and other depressants can contribute to coma, and in extreme cases, fatality.[_citation needed_]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ "Butalbital and Acetaminophen - FDA prescribing information, side effects and uses". drugs.com. Archived from the original on 2018-01-21.
  3. ^ DE Patent 526854
  4. ^ American Academy of Neurology (February 2013), "Five Things Physicians and Patients Should Question", Choosing Wisely: an initiative of the ABIM Foundation, American Academy of Neurology, archived from the original on September 1, 2013, retrieved August 1, 2013, which cites
  5. ^ a b American Headache Society (September 2013), "Five Things Physicians and Patients Should Question", Choosing Wisely: an initiative of the ABIM Foundation, American Headache Society, archived from the original on 3 December 2013, retrieved 10 December 2013, which cites