Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H8ClNS |
Molecular Weight | 161.652 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(CCCl)SC=N1
InChI
InChIKey=PCLITLDOTJTVDJ-UHFFFAOYSA-N
InChI=1S/C6H8ClNS/c1-5-6(2-3-7)9-4-8-5/h4H,2-3H2,1H3
Chlormethiazole has sedative, hypnotic, anticonvulsant and neuroprotective properties. This drug is approved in different counties under the different brand name (e.g., Heminevrin) and is used for the management of restlessness and agitation in the elderly, short-term treatment of severe insomnia in the elderly and treatment of alcohol withdrawal symptoms. Clomethiazole interacts with the picrotoxin/barbiturate site of the GABAA-receptor-chloride channel complex. Clomethiazole is pharmacologically distinct from both the benzodiazepines and the barbiturates. Given alone its effects on respiration are slight and the therapeutic index high.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: picrotoxin/barbiturate site of the GABAA-receptor-chloride channel complex Sources: https://www.ncbi.nlm.nih.gov/pubmed/2544811 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Heminevrin Approved UseClomethiazole is a short acting hypnotic and sedative with anticonvulsant effect. It is used for the: management of restlessness and agitation in the elderly, short term treatment of severe insomnia in the elderly and treatment of alcohol withdrawal symptoms where close hospital supervision is also provided. |
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Primary | Heminevrin Approved UseClomethiazole is a short acting hypnotic and sedative with anticonvulsant effect. It is used for the: management of restlessness and agitation in the elderly, short term treatment of severe insomnia in the elderly and treatment of alcohol withdrawal symptoms where close hospital supervision is also provided. |
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Primary | Heminevrin Approved UseClomethiazole is a short acting hypnotic and sedative with anticonvulsant effect. It is used for the: management of restlessness and agitation in the elderly, short term treatment of severe insomnia in the elderly and treatment of alcohol withdrawal symptoms where close hospital supervision is also provided. |
PubMed
Title | Date | PubMed |
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A single-dose study of the pharmacodynamic effects of chlormethiazole, temazepam and placebo in elderly parkinsonian patients. | 1991 Nov |
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The neurotoxic effects of methamphetamine on 5-hydroxytryptamine and dopamine in brain: evidence for the protective effect of chlormethiazole. | 1992 Apr |
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Inhibition of CYP2E1 activity does not abolish pulsatile urine alcohol concentrations during chronic alcohol infusions. | 1995 Jun 15 |
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Studies on the neuroprotective effect of the enantiomers of AR-A008055, a compound structurally related to clomethiazole, on MDMA ("ecstasy")-induced neurodegeneration in rat brain. | 2001 Aug |
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Neuroprotective efficacy of AR-A008055, a clomethiazole analogue, in a global model of acute ischaemic stroke and its effect on ischaemia-induced glutamate and GABA efflux in vitro. | 2001 Aug |
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Clomethiazole: an unsuccessful bachelor, but perhaps a prosperous married man? | 2002 Jan |
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[Diagnosis and treatment of delirium]. | 2002 Mar 13 |
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[Delirium in old age can be prevented and treated]. | 2002 Mar 20 |
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The vitamin-E analog trolox and the NMDA antagonist MK-801 protect pyramidal neurons in hippocampal slice cultures from IL-1beta-induced neurodegeneration. | 2003 |
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The effect of clomethiazole on plasma concentrations of interleukin-6, -8, -1beta, tumor necrosis factor-alpha, and neutrophil adhesion molecule expression during experimental extracorporeal circulation. | 2003 Jul |
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Treatment of acute alcohol withdrawal with gabapentin: results from a controlled two-center trial. | 2003 Oct |
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Changes in fatalities due to overdose of anxiolytic and sedative drugs in the UK (1983-1999). | 2004 |
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The effects of clomethiazole on polysomnographically recorded sleep in healthy subjects. | 2005 Aug |
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Ubiquitin-dependent degradation of p53 protein despite phosphorylation at its N terminus by acetaminophen. | 2006 Apr |
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Heart rate variability and sympathetic skin response in male patients suffering from acute alcohol withdrawal syndrome. | 2006 Sep |
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AMPA receptor activation reduces epileptiform activity in the rat neocortex. | 2007 Jul 16 |
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Association between inflammatory mediators and response to inhaled nitric oxide in a model of endotoxin-induced lung injury. | 2008 |
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Treatment with clomethiazole is associated with lower rates of premature discharge during alcohol withdrawal. | 2008 Jul |
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Neurotoxicity of drugs of abuse--the case of methylenedioxyamphetamines (MDMA, ecstasy), and amphetamines. | 2009 |
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Gamma hydroxybutyric acid (GHB) for the treatment of alcohol dependence: a review. | 2009 Jun |
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Impaired cerebral autoregulation during acute alcohol withdrawal. | 2010 Aug 1 |
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Sulforaphane prevents microcystin-LR-induced oxidative damage and apoptosis in BALB/c mice. | 2011 Aug 15 |
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Ethanol induction of CYP2A5: role of CYP2E1-ROS-Nrf2 pathway. | 2012 Aug |
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CMZ reversed chronic ethanol-induced disturbance of PPAR-α possibly by suppressing oxidative stress and PGC-1α acetylation, and activating the MAPK and GSK3β pathway. | 2014 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/33156
Management of restlessness and agitation in the elderly: one capsule three times daily.
Severe insomnia in the elderly: 1 - 2 capsules before going to bed. The lower dose should be tried first. As with all psychotropic drugs, treatment should be kept to a minimum, reviewed regularly and discontinued as soon as possible.
Alcohol withdrawal states: Clomethiazole is not a specific 'cure' for alcoholism. Alcohol withdrawal should be treated in hospital or, in exceptional circumstances, on an outpatient basis by specialist units when the daily dosage of clomethiazole must be monitored closely by community health staff. The dosage should be adjusted to patient response. The patient should be sedated but rousable. A suggested regimen is:
Initial dose:
Day 1, first 24 hours:
Day 2:
Day 3:
Days 4 to 6: 2 to 4 capsules, if necessary repeated after some hours.
9 to 12 capsules, divided into 3 or 4 doses.
6 to 8 capsules, divided into 3 or 4 doses.
4 to 6 capsules, divided into 3or 4 doses.
A gradual reduction in dosage until the final dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11082484
Using in vitro grease-gap recordings, it was shown that chlormethiazole inhibited epileptiform activity in neocortical slices superfused with Mg(2+)-free medium (IC(50) approximately 200 microM). At an antiepileptic concentration (300 microM), chlormethiazole potentiated the action of exogenously applied GABA (1 mM) but did not affect responses to the glutamate receptor agonists N-methyl-D-aspartate (10 microM) or L-quisqualic acid (3 microM). The GABA(A) receptor antagonist N-methyl-bicuculline (50 microM) reduced chlormethiazole's potency to inhibit the epileptiform activity. These results indicated that chlormethiazole's anticonvulsant action was likely mediated by potentiating GABA(A)ergic inhibition rather than by antagonising glutamatergic excitation.
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QN05CX04
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QN05CM02
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NCI_THESAURUS |
C29756
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2372
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m3645
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SUB06720MIG
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533-45-9
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C80664
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DB06470
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Clomethiazole
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)