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Butalbital

From Wikipedia, the free encyclopedia
Barbiturate drug used for headaches
Pharmaceutical compound
Butalbital
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601009
Routes of
administration
By mouth
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Bioavailability20-45%
MetabolismLiver mainlyCYP3A4
Eliminationhalf-life35 hours[2]
ExcretionKidney
Identifiers
  • 5-(2-Methylpropyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.926Edit 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 abarbiturate with an intermediate duration of action. Butalbital is often combined with other medications, such asparacetamol (acetaminophen) (asButalbital/acetaminophen) or aspirin, for the treatment ofpain andheadache. The various formulations combined withcodeine areFDA-approved for the treatment oftension headaches. Butalbital has the same chemical formula astalbutal but a different structure—one that presents as 5-allyl-5-isobutylbarbituric acid.[3]

Preparations

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Combinations include:

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

Contraindications

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There are specific treatments which are appropriate for targetingmigraines 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

[edit]

Side effects for any psychoactive drug are difficult to predict, though butalbital is usually well tolerated. Commonly reported side effects for butalbital, some of which tend to subside with continued use, include:

Rare side-effects includeStevens–Johnson syndrome, an adverse reaction to barbiturates, andanaphylaxis.

The risk and severity of all side effects is greatly increased when butalbital (or butalbital-containing medications) are combined with other sedatives (ex.ethanol,opiates,benzodiazepines,antihistamines). In particular, butalbital, especially when combined with other sedatives (e.g. opioids), 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 asgrapefruit and theblood orange. Taking butalbital-based medications with some other drugs may also increase the side effects of the other medication.

Dangers and risks

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Butalbital can causedependence oraddiction. Mixing withalcohol, benzodiazepines, and other CNS-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 CNS-depressants can contribute to coma, and in extreme cases, fatality.

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. Retrieved2023-08-16.
  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 theABIM Foundation, American Academy of Neurology,archived from the original on September 1, 2013, retrievedAugust 1, 2013, which cites
  5. ^abAmerican Headache Society (September 2013),"Five Things Physicians and Patients Should Question",Choosing Wisely: an initiative of theABIM Foundation,American Headache Society, archived fromthe original on 3 December 2013, retrieved10 December 2013, which cites

External links

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