NAV

Clomethiazole

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Clomethiazole
DrugBank Accession Number
DB06470
Background

Clomethiazole is a well-established γ-aminobutyric acid (GABAA)-mimetic drug. It is a sedative and hypnotic that is widely used in treating and preventing symptoms of acute alcohol withdrawal. It is a drug which 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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 161.65
Monoisotopic: 161.0065981
Chemical Formula
C6H8ClNS
Synonyms
  • Clomethiazole
  • Clomethiazolum
  • Clometiazol
External IDs
  • WY 1485
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Pharmacology

Indication

Investigated for use/treatment in strokes.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

clomethiazole interacts with the GABAA receptor complex. It inhibits the binding of [35S]butyl-bicyclophosphorothionate (TBPS), an effect indicative of GABAA receptor-channel activation, by increasing the rate of [35S]TBPS dissociation and decreasing the binding affinity. Gamma-aminobutyric acid (GABA), acting at GABAA receptors, is the main fast inhibitory neurotransmitter in mammalian central nervous system

TargetActionsOrganism
UGamma-aminobutyric acid receptor subunit alpha-1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Clomethiazole is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Clomethiazole can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Clomethiazole can be increased when combined with Abatacept.
AcetaminophenThe metabolism of Clomethiazole can be decreased when combined with Acetaminophen.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Clomethiazole.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Clomethiazole hydrochloride85223EMG446001-74-7OFXYKSLKNMTBHK-UHFFFAOYSA-N
International/Other Brands
Zendra

Categories

ATC Codes
N05CX04 — Clomethiazole, combinationsN05CM02 — Clomethiazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at positions 4 and 5 only.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Thiazoles
Direct Parent
4,5-disubstituted thiazoles
Alternative Parents
Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
4,5-disubstituted 1,3-thiazole / Alkyl chloride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organochloride / Organohalogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
a thiazole (CPD-10432)
Affected organisms
Not Available

Chemical Identifiers

UNII
0C5DBZ19HV
CAS number
533-45-9
InChI Key
PCLITLDOTJTVDJ-UHFFFAOYSA-N
InChI
InChI=1S/C6H8ClNS/c1-5-6(2-3-7)9-4-8-5/h4H,2-3H2,1H3
IUPAC Name
5-(2-chloroethyl)-4-methyl-1,3-thiazole
SMILES
CC1=C(CCCl)SC=N1

References

General References
  1. Lyden PD, Ashwood T, Claesson L, Odergren T, Friday GH, Martin-Munley S: The clomethiazole acute stroke study in ischemic, hemorrhagic, and t-PA treated stroke: Design of a phase III trial in the united states and canada. J Stroke Cerebrovasc Dis. 1998 Nov-Dec;7(6):435-41. [Article]
  2. Millis SR, Straube D, Iramaneerat C, Smith EV Jr, Lyden P: Measurement properties of the National Institutes of Health Stroke Scale for people with right- and left-hemisphere lesions: further analysis of the clomethiazole for acute stroke study-ischemic (class-I) trial. Arch Phys Med Rehabil. 2007 Mar;88(3):302-8. [Article]
PubChem Compound
10783
PubChem Substance
347827773
ChemSpider
10327
BindingDB
234400
RxNav
2372
ChEBI
92875
ChEMBL
CHEMBL315795
ZINC
ZINC000000001192
Wikipedia
Chlormethiazole

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentAnxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.674 mg/mLALOGPS
logP2.47ALOGPS
logP1.77Chemaxon
logS-2.4ALOGPS
pKa (Strongest Basic)3.18Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area12.89 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity40.37 m3·mol-1Chemaxon
Polarizability16.14 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-1900000000-2dd7f3979630b50034d8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00or-6900000000-262f9e1f2dd09a728ec5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9300000000-58322f89a0f8cb03a68e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-e08623b3bf46b90d454a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-9000000000-f3b4cb1a637ef1daf4c6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-9000000000-5415bc757f3bd48b346d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-132.80531
predicted
DeepCCS 1.0 (2019)
[M+H]+136.13063
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.74841
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Gamma-aminobutyric acid receptor subunit alpha-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da

Enzymes

Details1. Cytochrome P450 2A6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Details2. Cytochrome P450 2B6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Details3. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Details4. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Drug created at March 19, 2008 16:34 / Updated at February 21, 2021 18:52