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Butalbital

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Butalbital
Clinical data
Other names5-allyl-5-isobutylbarbituric acid
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601009
Routes of
administration		By mouth
Drug classBarbiturate
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Bioavailability20-45%
MetabolismLiver mainly CYP3A4
Elimination half-life35 hours[2]
ExcretionKidney
Identifiers
  • 5-(2-Methylpropyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.926 Edit this at Wikidata
Chemical and physical data
FormulaC11H16N2O3
Molar mass224.260 g·mol−1
3D model (JSmol)
  • O=C1NC(=O)NC(=O)C1(CC(C)C)C\C=C
  • 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) checkY
  • Key: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]

Available forms

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Combinations include:[citation needed]

  • Butalbital/acetaminophen, Butalbital and acetaminophen (paracetamol), (trade names: Axocet, Bucet, Bupap, Cephadyn, Dolgic, Phrenilin, Forte, Sedapap)
  • Butalbital/paracetamol/caffeine (trade names: Fioricet, Esgic, Esgic-Plus, Orbivan, Fiormor, Fiortal, Fortabs, Laniroif)
  • Butalbital/caffeine/codeine (trade name: Fioricet#3 with Codeine)
  • Butalbital/aspirin (trade name: Axotal)
  • Butalbital/aspirin/caffeine (trade name: Fiorinal)
  • Butalbital/aspirin/caffeine/codeine (trade name: Fiorinal#3 with Codeine)
  • Ergotamine/caffeine/butalbital/belladonna alkaloids (trade name: Cafergot-PB)

Contraindications

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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

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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]

Interactions

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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]

References

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  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
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