Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Chlormezanone
- DrugBank Accession Number
- DB01178
- Background
A non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Chlormezanone (DB01178)
- Weight
- Average: 273.736
Monoisotopic: 273.022641652 - Chemical Formula
- C11H12ClNO3S
- Synonyms
- (±)-chlormezanone
- 2-(p-chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide
- 2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
- Chlormethazanone
- Chlormezanona
- Chlormezanone
- Chlormézanone
- Chlormezanonum
- Clormezanona
Pharmacology
- Indication
Used in the management of anxiety and in the treatment of muscle spasm.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Chlormezanone is a non-benzodiazepine muscle relaxant. It was discontinued worldwide in 1996 by its manufacturer due to confirmed serious and rare cutaneous reactions (toxic epidermal necrolysis).
- Mechanism of action
Chlormezanone binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.
Target Actions Organism ATranslocator protein agonistHumans - 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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include drowsiness, weakness, nausea, dizziness, abdominal pain, cerebral oedema and renal tubular necrosis, hyperglycaemia and hypoglycaemia, liver damage, encephalopathy, coma and death.
- 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 CNS depression can be increased when Chlormezanone is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Chlormezanone. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Chlormezanone. Agomelatine The risk or severity of CNS depression can be increased when Chlormezanone is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Chlormezanone. - Food Interactions
- 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.- International/Other Brands
- Fenaprim / Trancopal (WinthropSreon)
Categories
- ATC Codes
- M03BB02 — Chlormezanone
- M03BB — Oxazol, thiazine, and triazine derivatives
- M03B — MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
- M03 — MUSCLE RELAXANTS
- M — MUSCULO-SKELETAL SYSTEM
- M03BB — Oxazol, thiazine, and triazine derivatives
- M03B — MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
- M03 — MUSCLE RELAXANTS
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Anti-Anxiety Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Musculo-Skeletal System
- Neuromuscular Agents
- Oxazol, Thiazine, and Triazine Derivatives
- Peripheral Nervous System Agents
- Psychotropic Drugs
- Sulfur Compounds
- Thiazines
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Chlorobenzenes
- Alternative Parents
- Thiazinanes / Aryl chlorides / Tertiary carboxylic acid amides / Sulfones / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides show 2 more
- Substituents
- 1,3-thiazinane / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Chlorobenzene / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfone, lactam, monochlorobenzenes, 1,3-thiazine (CHEBI:3619)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- GP568V9G19
- CAS number
- 80-77-3
- InChI Key
- WEQAYVWKMWHEJO-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3
- IUPAC Name
- 2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione
- SMILES
- CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
References
- General References
- Wollina U, Hipler UC, Seeling A, Oelschlager H: Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro. Skin Pharmacol Physiol. 2005 May-Jun;18(3):132-8. [Article]
- Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]. Pharmazie. 2000 Apr;55(4):293-6. [Article]
- Oelschlager H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, Machts H, Riederer H, Rackur H: [Cleavage and biotransformation of the central muscle relaxant chlormezanone]. Pharmazie. 1998 Sep;53(9):620-4. [Article]
- Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers]. Therapie. 1990 Jul-Aug;45(4):315-9. [Article]
- External Links
- Human Metabolome Database
- HMDB0015309
- KEGG Drug
- D00268
- PubChem Compound
- 2717
- PubChem Substance
- 46505352
- ChemSpider
- 2616
- 2373
- ChEBI
- 3619
- ChEMBL
- CHEMBL1200714
- Therapeutic Targets Database
- DAP001252
- PharmGKB
- PA448939
- Wikipedia
- Chlormezanone
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Bipolar Disorder (BD) / Psychosis / Schizoaffective Disorders / Schizophrenia / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 1 Completed Not Available Axonal Change, Neuronal / Pain 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 116.2-118.6 Merck Index 2072 water solubility 2500 mg/L (at 25 °C) MERCK INDEX (1996) logP 1.3 Not Available - Predicted Properties
Property Value Source Water Solubility 1.61 mg/mL ALOGPS logP 0.84 ALOGPS logP 0.92 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 19.07 Chemaxon pKa (Strongest Basic) -2.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 54.45 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 64.88 m3·mol-1 Chemaxon Polarizability 25.72 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9167 Blood Brain Barrier + 0.9383 Caco-2 permeable - 0.5597 P-glycoprotein substrate Non-substrate 0.6347 P-glycoprotein inhibitor I Non-inhibitor 0.6885 P-glycoprotein inhibitor II Non-inhibitor 0.9959 Renal organic cation transporter Non-inhibitor 0.7164 CYP450 2C9 substrate Non-substrate 0.6022 CYP450 2D6 substrate Non-substrate 0.7983 CYP450 3A4 substrate Substrate 0.6616 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9375 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5186 Ames test Non AMES toxic 0.6263 Carcinogenicity Non-carcinogens 0.7622 Biodegradation Not ready biodegradable 0.6329 Rat acute toxicity 2.6246 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9892 hERG inhibition (predictor II) Non-inhibitor 0.7018
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.3033113 predictedDarkChem Lite v0.1.0 [M-H]- 152.28612 predictedDeepCCS 1.0 (2019) [M+H]+ 157.4480113 predictedDarkChem Lite v0.1.0 [M+H]+ 154.68167 predictedDeepCCS 1.0 (2019) [M+Na]+ 157.1610113 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.68452 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678)
- Specific Function
- androgen binding
- Gene Name
- TSPO
- Uniprot ID
- P30536
- Uniprot Name
- Translocator protein
- Molecular Weight
- 18827.81 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:25