Carisoprodol

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Carisoprodol
other names	( RS ) -Isopropylcarbamic acid-2-carbamoyloxymethyl-2-methylpentyl ester ( IUPAC )
Molecular formula	C 12 H 24 N 2 O 4
External identifiers / databases
EC number	201-118-7
ECHA InfoCard	100.001.017
PubChem	2576
DrugBank	DB00395
Wikidata	Q416905
Drug information
ATC code	M03 BA02
Drug class	Muscle relaxants
properties
Molar mass	260.33 g mol −1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	1320 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carisoprodol [trade name: Soma (USA)] is a centrally acting muscle relaxant , the active metabolite of which is meprobamate .

Indications

Neurogenic muscle spasms (cramps) and certain arthritis forms , for example, at a paravertebral (next to the spine) muscle tension due to a spinal - degeneration . Carisoprodol relaxes the muscles. It relieves the pain of tension, sprains , spasms or other muscular injuries.

Carisoprodol is not a pain reliever. It should therefore not be used to treat general body pain.

Side effects and allergies

Taking Carisoprodol can cause stomach upset , heartburn , headache , dizziness or drowsiness . Allergic reactions to carisoprodol are very rare. Symptoms can include a rash , itching , swelling , dizziness, and difficulty breathing .

Carisoprodol has described a possible acute urticaria ( hives ) and a fixed drug eruption as an allergic reaction .

Carisoprodol is also excreted in breast milk. Breastfeeding mothers should therefore refrain from taking Carisoprodol preparations.

Pharmacokinetics

Carisoprodol is absorbed by the body quite quickly. The effect sets in after about 30 minutes and lasts for about two to six hours. It is metabolized in the liver using cytochrome P450 and the isoenzyme CYP2C19 . The half-life is around eight hours. Excretion takes place renally . A significant proportion of carisoprodol is metabolized to meprobamate . The sedative meprobamate is known for abuse and addiction. This explains the potential for abuse of carisoprodol.

history

On June 1, 1959, several American pharmacologists met at Wayne State University in Detroit / Michigan to discuss the newly developed drug Carisoprodol. Originally it was thought that Carisoprodol had an antiseptic effect, but then the central muscle relaxing properties were discovered. Carisoprodol was developed by Frank M. Berger at Wallace Laboratories . The development was based on Meprobamat . The substitution of a hydrogen - atom by isopropyl obtain group at one of the two carbamyl nitrogen atoms was made with the intention of a molecule with new pharmacological properties.

The trade name of Carisoprodol when it was first launched in 1959 was Soma . The Greek word σῶμα (sṓma) means body . The name Soma is also the name of a fictional drug in Aldous Huxley's 1932 novel Brave New World .

literature

JG Bramness et al .: Carisoprodol use and abuse in Norway. A pharmacoepidemiological study. In: Br J Clin Pharmacol . 2/2007, pp. 210-218.
I. Kamin, D. Shaskan: Death due to massive overdose of meprobamate. In: Am J Psychiatry. 115/1959, pp. 1123-1124.
LE Hollister: The pre-benzodiazepine era. In: J Psychoactive Drugs. 15/1983, pp. 9-13.
Y. Gaillard et al: Meprobamate overdosage: a continuing problem. Sensitive GC-MS quantitation after solid phase extraction in 19 fatal cases. In: Forensic Sci.Int. 86/1997, pp. 173-180.
MD Allen et al .: Meprobamate overdosage: a continuing problem. In: J Toxicol Clin Toxicol . , 11/1977, pp. 501-515.
P. Kintz et al: Fatal meprobamate self-poisoning. In: Am J Forensic Med Pathol. 9/1988, pp. 139-140.
E. Eeckhout et al: Meprobamate poisoning, hypotension and the Swan-Ganz catheter. In: Intensive Care Med. 14/1988, pp. 437-438.
F. Lhoste et al .: Treatment of hypotension in meprobamate poisoning. In: N Engl J Med , 296/1977, p. 1004.
H. Bedson: Coma due to meprobamate intoxication. Report of a case confirmed by chemical analysis. In: The Lancet . 273/1959, pp. 288-290.
A. Blumberg et al .: Severe hypotension reactions following meprobamate overdosage. In: Ann Intern Med . 51/1959, pp. 607-612.

Individual evidence

↑ ^a ^b ^c data sheet Carisoprodol from Sigma-Aldrich , accessed on March 15, 2011 ( PDF ).
↑ Fernández-Rivas et al: Urticaria to carisoprodol. In: Allergy. 57/2002, p. 55.
↑ JG Miller, (Ed.): The pharmacology and clinical usefulness of carisoprodol. Wayne State University, Detroit 1959.
^ F. Berger et al .: The history, chemistry, and pharmacology of carisoprodol. In: Annals of the New York Academy of Sciences . 86/1959, pp. 90-107.
↑ Time Magazine, June 8, 1959: Brave New Soma .

[Sigma-1] ta sheet Carisoprodol from Sigma-Aldrich , accessed on March 15, 2011 ( PDF ).

[2] Fernández-Rivas et al: Urticaria to carisoprodol. In: Allergy. 57/2002, p. 55.

[3] JG Miller, (Ed.): The pharmacology and clinical usefulness of carisoprodol. Wayne State University, Detroit 1959.

[4] F. Berger et al .: The history, chemistry, and pharmacology of carisoprodol. In: Annals of the New York Academy of Sciences . 86/1959, pp. 90-107.

[5] Time Magazine, June 8, 1959: Brave New Soma .