Butalbital

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Butalbital
Systematic (IUPAC) name
5-(2-methylpropyl)-5-(2-propenyl)-
2,4,6(1H,3H,5H)-pyrimidinetrione
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601009
Pregnancy cat.C (US)
Legal statusSchedule III (US)
Routesoral
Pharmacokinetic data
Bioavailability20-45%
Metabolismhepatic
Half-life35 hours [1]
Excretionrenal
Identifiers
CAS number77-26-9 YesY
ATC codeNone
PubChemCID 2481
DrugBankDB00241
ChemSpider2387 YesY
UNIIKHS0AZ4JVK YesY
KEGGD03182 YesY
ChEBICHEBI:102524 YesY
ChEMBLCHEMBL454 YesY
Chemical data
FormulaC11H16N2O3 
Mol. mass224.256
 YesY (what is this?)  (verify)
 
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Butalbital
Systematic (IUPAC) name
5-(2-methylpropyl)-5-(2-propenyl)-
2,4,6(1H,3H,5H)-pyrimidinetrione
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601009
Pregnancy cat.C (US)
Legal statusSchedule III (US)
Routesoral
Pharmacokinetic data
Bioavailability20-45%
Metabolismhepatic
Half-life35 hours [1]
Excretionrenal
Identifiers
CAS number77-26-9 YesY
ATC codeNone
PubChemCID 2481
DrugBankDB00241
ChemSpider2387 YesY
UNIIKHS0AZ4JVK YesY
KEGGD03182 YesY
ChEBICHEBI:102524 YesY
ChEMBLCHEMBL454 YesY
Chemical data
FormulaC11H16N2O3 
Mol. mass224.256
 YesY (what is this?)  (verify)

Butalbital is a barbiturate with an intermediate duration of action. Butalbital is often combined with other medications, such as acetaminophen (paracetamol) or aspirin, and is commonly prescribed 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,[2]

Preparations[edit]

Combinations include:

Contraindications[edit]

Butalbital is contraindicated as a first-line treatment for headache because it impairs alertness, brings risk of dependence and addiction, and increases the risk that episodic headaches will become chronic.[3] Opioids also can cause heightened sensitivity to headache pain.[3] When other treatments fail or are unavailable, butalbital may be appropriate for treating headache if the patient can be monitored to prevent the development of chronic headache.[3]

There are specific treatments which are appropriate for targeting migraines and headaches which are preferable to butalbital when available as an option.[4] It is a least preferable option to be used if other available treatments fail.[4]

Side effects[edit]

Side effects for any psychoactive drug are difficult to predict, but commonly reported side effects for butalbital include:

Fioricet (50/40/325)

(Rare side-effects include Stevens–Johnson syndrome, an adverse reaction to barbiturates.)

There are other potential side effects; this list should not be considered all-inclusive.

Dangers and Risks[edit]

Butalbital is a physically and psychologically addictive barbiturate. Butalbital should not be mixed with alcohol due to increased risk of intoxication, increased respiratory depression, and increased liver toxicity when it is a butalbital combination including paracetamol (acetaminophen). Many opioid-dependent persons frequently use barbiturates as a potentiator to their normal dose of opiates in order to increase the effects, or with a less than normal dose as means of conserving their supply. Especially when used with the stronger Schedule II narcotics, suicide or accidental death occurs much more frequently than first reported with one drug alone. Use of alcohol, benzodiazepines, and other CNS-depressants often also contribute to respiratory depression, coma, and in extreme cases fatality. There are other potential risks; this list should not be considered all-inclusive.

When benzodiazepines are co-administered with barbiturates, the sum effect of the drugs is far greater than would be expected considering the effect of both drugs separately. This is due to complimentary mechanisms at the GABAA receptor, where benzodiazepines increase the rate of chloride channel opening while barbiturates increase the duration. Say a dose of a benzodiazepine causes a channel which normally opens once every 30 seconds to open 3 times faster, while a barbiturate causes the channel to pass 3 chloride ions per opening instead of the normal 1. When combined, the channel is now passing 9 ions every 30 seconds instead of one, a 9-fold increase in activity.

In Hong Kong, butalbital is regulated as a psychotropic substance. There are regulations governing the retail sale, wholesale and supply on prescription at community pharmacy.

United Kingdom[edit]

Butalbital, or any preparation containing it, is a Schedule III CD (Controlled Drug) under the Misuse of Drugs Act 1971 as amended, but is not, nor has it been, available in the UK despite there having been calls for it to be made available on the NHS (National Health Service); this has been growing in recent years as more migraine sufferers have been prescribed Fioricet, Fiorinal or other preparation whilst on holiday in the USA;

References[edit]

  1. ^ http://www.drugs.com/pro/butalbital-and-acetaminophen.html
  2. ^ DE Patent 526854
  3. ^ a b c American Headache Society (September 2013), "Five Things Physicians and Patients Should Question", Choosing Wisely: an initiative of the ABIM Foundation (American Headache Society), retrieved 10 December 2013 , which cites
    • Bigal, M. E.; Lipton, R. B. (2009). "Excessive opioid use and the development of chronic migraine". Pain 142 (3): 179–182. doi:10.1016/j.pain.2009.01.013 . PMID 19232469.  edit
    • Bigal, M. E.; Serrano, D.; Buse, D.; Scher, A.; Stewart, W. F.; Lipton, R. B. (2008). "Acute Migraine Medications and Evolution from Episodic to Chronic Migraine: A Longitudinal Population-Based Study". Headache: the Journal of Head and Face Pain 48 (8): 1157–1168. doi:10.1111/j.1526-4610.2008.01217.x . PMID 18808500.  edit
    • Scher, A. I.; Stewart, W. F.; Ricci, J. A.; Lipton, R. B. (2003). "Factors associated with the onset and remission of chronic daily headache in a population-based study". Pain 106 (1–2): 81–89. doi:10.1016/S0304-3959(03)00293-8 . PMID 14581114.  edit
    • Katsarava, Z.; Schneeweiss, S.; Kurth, T.; Kroener, U.; Fritsche, G.; Eikermann, A.; Diener, H. C.; Limmroth, V. (2004). "Incidence and predictors for chronicity of headache in patients with episodic migraine". Neurology 62 (5): 788–790. doi:10.1212/01.WNL.0000113747.18760.D2 . PMID 15007133.  edit
  4. ^ a b 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), retrieved August 1, 2013 , which cites
      • Silberstein, S. D. (2000). "Practice parameter: Evidence-based guidelines for migraine headache (an evidence-based review): Report of the Quality Standards Subcommittee of the American Academy of Neurology". Neurology 55 (6): 754–762. doi:10.1212/WNL.55.6.754 . PMID 10993991.  edit
      • Evers, S.; Afra, J.; Frese, A.; Goadsby, P. J.; Linde, M.; May, A.; Sándor, P. S.; European Federation of Neurological Societies (2009). "EFNS guideline on the drug treatment of migraine - revised report of an EFNS task force". European Journal of Neurology 16 (9): 968–981. doi:10.1111/j.1468-1331.2009.02748.x . PMID 19708964.  edit
      • Institute for Clinical Systems Improvement (2011), Headache, Diagnosis and Treatment of, Institute for Clinical Systems Improvement 

External links[edit]

"Butalbital". On-line Medical Dictionary. Retrieved June 26, 2005.  "Butalbital and Acetaminophen (Systemic)". MedicinePlus Drug Information. Archived from the original on December 30, 2006. Retrieved December 31, 2006.  "Controlled Substances in Schedule III". Drug Enforcement Administration. 2007. Retrieved 2007-01-13.