Clomethiazole

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Clomethiazole
Clomethiazole structure.svg
Clomethiazole ball-and-stick model.png
Systematic (IUPAC) name
5-(2-Chloroethyl)-4-methyl-1,3-thiazole
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • UK: POM (Prescription only)
Routes of
administration
Oral
Pharmacokinetic data
Biological half-life 3.6–5 hours
Identifiers
CAS Number 533-45-9 N
ATC code N05CM02 (WHO)
PubChem CID: 10783
ChemSpider 10327 YesY
UNII 0C5DBZ19HV YesY
KEGG D07330 YesY
ChEMBL CHEMBL315795 YesY
Chemical data
Formula C6H8ClNS
Molecular mass 161.653 g/mol
  • ClCCC1=C(C)N=CS1
  • InChI=1S/C6H8ClNS/c1-5-6(2-3-7)9-4-8-5/h4H,2-3H2,1H3 YesY
  • Key:PCLITLDOTJTVDJ-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Clomethiazole (also called chlormethiazole) is a sedative and hypnotic originally developed by Hoffmann-La Roche in the 1930s.[1] The drug is used in treating and preventing symptoms of acute alcohol withdrawal.

It is structurally related to thiamine (vitamin B1), but acts like a sedative, hypnotic, muscle relaxant and anticonvulsant. It is also used for the management of agitation, restlessness, short-term insomnia and Parkinson's disease in the elderly. In the UK, it is sold under the brand Heminevrin (AstraZeneca Pharmaceuticals). Another brand name includes Nevrin in Romania, Distraneurin in Germany and Distraneurine in Spain. The drug is marketed either as a free base in an oily suspension containing 192 mg in capsule form, or as clomethiazole edisylate syrup.

Pharmacology

Chlomethiazole acts as a positive allosteric modulator at the barbiturate/picrotoxin site of the GABAA receptor. It works to enhance the action of the neurotransmitter GABA at this receptor.[citation needed] GABA is the major inhibitory neurotransmitter in the brain and produces anxiolytic, anticonvulsant, sedative, and hypnotic effects. Chlomethiazole appears to also have another mechanism of action mediating some of its hypothermic and neuroprotective effects.[citation needed]

Adverse effects

Long term and frequent use of chlomethiazole can cause tolerance and physical dependence. Abrupt withdrawal may result in symptoms similar to those of sudden withdrawal of alcohol or benzodiazepines.[2]

Overdose

Chlomethiazole is particularly toxic and dangerous in overdose and can be potentially fatal. Alcohol multiplies the effect. As the drug can be fatal in high doses, prescribing clomethiazole outside a controlled environment, like a hospital, is not recommended, especially because there are much less toxic alternatives, such as diazepam. Diazepam is one of many drugs belonging to the benzodiazepine class, with a long half-life (50–100 hours) and a very low risk of fatal overdose, as long as the patient does not consume alcohol or certain other types of medication.[3]

Drummer Keith Moon of the rock band The Who died of a clomethiazole overdose.[4]

References

  1. CH patent 200248, "Verfahren zur Darstellung von 4-Methyl-5-B-chloräthylthiazol", issued 1938-09-30, assigned to Hoffmann-La Roche 
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