Butalbital

Butalbital

Systematic (IUPAC) name
5-(2-methylpropyl)-5-(2-propenyl)- 2,4,6(1H,3H,5H)-pyrimidinetrione
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601009
Pregnancy cat.	D(US)
Legal status	Schedule III (US)
Routes	oral
Pharmacokinetic data
Bioavailability	20-45%
Metabolism	hepatic
Half-life	35 hours [1]
Excretion	renal
Identifiers
CAS number	77-26-9 Y
ATC code	None
PubChem	CID 2481
DrugBank	APRD00266
ChemSpider	2387 Y
UNII	KHS0AZ4JVK Y
KEGG	D03182 Y
ChEBI	CHEBI:102524 Y
ChEMBL	CHEMBL454 Y
Chemical data
Formula	C11H16N2O3
Mol. mass	224.256
SMILES	eMolecules & PubChem
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) Y Key:UZVHFVZFNXBMQJ-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Butalbital, structure presents as 5-allyl-5-isobutylbarbituric acid,^[2] is a barbiturate with an intermediate duration of action. It has the same chemical formula as talbutal but a different structure. 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.

Combinations include:

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

Side effects

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

Dizziness Drowsiness Intoxicated feeling Light-headedness Nausea Sedation Euphoria Addiction Severe impairment of judgment Diarrhea Memory Loss Constipation

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

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. 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. This is why Butalbital is frequently encountered with other deterrents dangerous in higher doses such as, almost always, Paracetamol/Aspirin and Caffeine(much like Tylenol #3, Vicodin, Percocet). There are other potential risks; this list should not be considered all-inclusive.

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

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; 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; many have found it a far superior treatment than any available NHS or OTC treatment back home. There has consequently been a boom in the number of orders made for these preparations at online pharmacies in the US (very few US Pharmacies ship to the UK, unlike the other way around). The other medicine British holidaymakers have found more effective, for the same conditions, than they would use at home is hydrocodone/paracetamol combinations, which many visitors to Florida especially were prescribed when asking for dihydrocodeine, an extremely close relative also prescribed for mild to moderate pain. The biggest difference is in the much higher pricing of medications in the US. In Scotland, unlike other parts of the UK, all prescriptions are included in one's taxes (except Private Prescriptions). Elsewhere, there is a charge of a few pounds per item.

References

1. ^ http://www.drugs.com/pro/butalbital-and-acetaminophen.html
2. ^ DE Patent 526854

External links

"Butalbital". On-line Medical Dictionary. http://cancerweb.ncl.ac.uk/cgi-bin/omd?query=butalbital&action=Search+OMD. Retrieved June 26, 2005.  "Butalbital and Acetaminophen (Systemic)". MedicinePlus Drug Information. Archived from the original on December 30, 2006. http://web.archive.org/web/20061230122834/http://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202102.html. Retrieved December 31, 2006.  "Controlled Substances in Schedule III". Drug Enforcement Administration. 2007. http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched3.htm. Retrieved 2007-01-13.