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
Structure for Clomethiazole (DB06470)
- Weight
- Average: 161.65
Monoisotopic: 161.0065981 - Chemical Formula
- C6H8ClNS
- Synonyms
- Clomethiazole
- Clomethiazolum
- Clometiazol
- External IDs
- WY 1485
Pharmacology
- Indication
Investigated for use/treatment in strokes.
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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
Target Actions Organism UGamma-aminobutyric acid receptor subunit alpha-1 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Clomethiazole is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Clomethiazole can be increased when it is combined with Abametapir. Abatacept The metabolism of Clomethiazole can be increased when combined with Abatacept. Acetaminophen The metabolism of Clomethiazole can be decreased when combined with Acetaminophen. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Clomethiazole. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Clomethiazole. Adalimumab The metabolism of Clomethiazole can be increased when combined with Adalimumab. Agomelatine The risk or severity of adverse effects can be increased when Clomethiazole is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Clomethiazole. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Clomethiazole. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Clomethiazole hydrochloride 85223EMG44 6001-74-7 OFXYKSLKNMTBHK-UHFFFAOYSA-N - International/Other Brands
- Zendra
Categories
- ATC Codes
- N05CX04 — Clomethiazole, combinations
- N05CX — Hypnotics and sedatives in combination, excl. barbiturates
- N05C — HYPNOTICS AND SEDATIVES
- N05 — PSYCHOLEPTICS
- N — NERVOUS SYSTEM
- Drug Categories
- Anticonvulsants
- Central Nervous System Agents
- Central Nervous System Depressants
- Compounds used in a research, industrial, or household setting
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- GABA Agents
- GABA Modulators
- Hypnotics and Sedatives
- Nervous System
- Neuroprotective Agents
- Neurotransmitter Agents
- Protective Agents
- Psycholeptics
- Sulfur Compounds
- Thiazoles
- 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
- 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]
- 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]
- External Links
- PubChem Compound
- 10783
- PubChem Substance
- 347827773
- ChemSpider
- 10327
- BindingDB
- 234400
- 2372
- ChEBI
- 92875
- ChEMBL
- CHEMBL315795
- ZINC
- ZINC000000001192
- Wikipedia
- Chlormethiazole
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1
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
Property Value Source Water Solubility 0.674 mg/mL ALOGPS logP 2.47 ALOGPS logP 1.77 Chemaxon logS -2.4 ALOGPS pKa (Strongest Basic) 3.18 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.89 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 40.37 m3·mol-1 Chemaxon Polarizability 16.14 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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
- 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]
- 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
- 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]
- 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
- 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]
- 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
- 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