DrugBank: Chlormezanone (DB01178)

targets (1)

Identification

Name

Chlormezanone

Accession Number

DB01178 (APRD00865)

Type

small molecule

Groups

approved, withdrawn

Description

A non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Chlormethazanone
Chlormethazone
Chlormezanon
Chlormezanone [BAN:INN:JAN]
Chlormezanonum [INN-Latin]
Clormetazanone
Clormetazon
Clormezanona [INN-Spanish]
Clormezanone [DCIT]
Dichloromethazanone
Dichloromezanone
dl-Chlormezanone

Salts

Not Available

Brand names

Name	Company
Alinam
Banabil-sintyal
Banabin
Banabin-Sintyal
Banabin-syntyal
Bisina
Chlomedinon
Clorilax
Lobak
Mio-Sed
Miorilax
Muskel
Muskel-Trancopal
Myolespen
Phenarol
Rexan
Rilansyl
Rilaquil
Rilasol
Rilassol
Rilax
Rillasol
Supotran
Suprotan
Tanafol
Trancopal
Trancote
Tranrilax
Transanate

Brand mixtures

Brand Name	Ingredients
Myoflex	Paracetamol + Chlormezanone

Categories

Anti-anxiety Agents
Benzodiazepines
Antipsychotics
Muscle Relaxants, Central

CAS number

80-77-3

Weight

Average: 273.736
Monoisotopic: 273.022641652

Chemical Formula

C₁₁H₁₂ClNO₃S

InChI Key

InChIKey=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

Plain Text

IUPAC Name

2-(4-chlorophenyl)-3-methyl-1$l^{6},3-thiazinane-1,1,4-trione

SMILES

CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Benzene and Derivatives
Halobenzenes
Lactams

Substructures

Amino Ketones
Sulfonyls
Benzene and Derivatives
Aliphatic and Aryl Amines
Aryl Halides
Halobenzenes
Sulfones
Heterocyclic compounds
Aromatic compounds
Carboxamides and Derivatives
Lactams
Sulfoxides

Pharmacology

Indication

Used in the management of anxiety and in the treatment of muscle spasm.

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.

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

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.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Sanofi aventis us llc

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	116.2 °C	PhysProp
water solubility	2500 mg/L (at 25 °C)	MERCK INDEX (1996)
logP	1.3	Not Available

Predicted Properties

Property	Value	Source
water solubility	1.61e+00 g/l	ALOGPS
logP	0.84	ALOGPS
logP	0.92	ChemAxon
logS	-2.2	ALOGPS
pKa (strongest acidic)	19.07	ChemAxon
pKa (strongest basic)	-2.5	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	3	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	54.45	ChemAxon
rotatable bond count	1	ChemAxon
refractivity	64.88	ChemAxon
polarizability	25.89	ChemAxon

References

Synthesis Reference

Not Available

General Reference

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. Pubmed
Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] Pharmazie. 2000 Apr;55(4):293-6. Pubmed
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. Pubmed
Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers] Therapie. 1990 Jul-Aug;45(4):315-9. Pubmed

External Links

Resource	Link
KEGG Drug	D00268
PubChem Compound	2717
PubChem Substance	46505352
ChemSpider	2616
ChEBI	3619
ChEMBL	3619
Therapeutic Targets Database	DAP001252
PharmGKB	PA448939
Wikipedia	http://en.wikipedia.org/wiki/Chlormezanone

ATC Codes

M03BB02

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Translocator protein Pharmacological action: yes Actions: agonist Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme Organism class: human UniProt ID: P30536 Gene: TSPO Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Translocator protein

Pharmacological action: yes
Actions: agonist

Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme

Organism class: human
UniProt ID: P30536 Link_out

Gene: TSPO Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19