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Identification
NameChlormezanone
Accession NumberDB01178  (APRD00865)
Typesmall molecule
Groupsapproved, withdrawn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
Thumb
Synonyms
SynonymLanguageCode
(+-)-ChlormezanoneNot AvailableNot Available
(±)-chlormezanoneNot AvailableNot Available
2-(P-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxideNot AvailableNot Available
2-(P-Chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxideNot AvailableNot Available
ChlormethazanoneNot AvailableNot Available
ChlormezanonaNot AvailableNot Available
ChlormezanoneNot AvailableINN, BAN, JAN
ChlormezanonumLatinINN
ClormezanonaSpanishINN
SaltsNot Available
Brand names
NameCompany
FenaprimNot Available
TrancopalWinthropSreon
Brand mixtures
Brand NameIngredients
MyoflexParacetamol + Chlormezanone
Categories
CAS number80-77-3
WeightAverage: 273.736
Monoisotopic: 273.022641652
Chemical FormulaC11H12ClNO3S
InChI KeyWEQAYVWKMWHEJO-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-1$l^{6},3-thiazinane-1,1,4-trione
SMILES
CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassHalobenzenes
Direct parentChlorobenzenes
Alternative parentsThiazinanes; Aryl Chlorides; Sulfones; Tertiary Carboxylic Acid Amides; Tertiary Amines; Sulfoxides; Carboxylic Acids; Polyamines; Organochlorides
Substituentsaryl chloride; aryl halide; 1,3-thiazinane; sulfone; tertiary carboxylic acid amide; tertiary amine; sulfoxide; carboxamide group; polyamine; carboxylic acid derivative; carboxylic acid; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
Pharmacology
IndicationUsed in the management of anxiety and in the treatment of muscle spasm.
PharmacodynamicsChlormezanone 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 actionChlormezanone 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point116.2-118.6Merck Index 2072
water solubility2500 mg/L (at 25 °C)MERCK INDEX (1996)
logP1.3Not Available
Predicted Properties
PropertyValueSource
water solubility1.61e+00 g/lALOGPS
logP0.84ALOGPS
logP0.92ChemAxon
logS-2.2ALOGPS
pKa (strongest acidic)19.07ChemAxon
pKa (strongest basic)-2.5ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area54.45ChemAxon
rotatable bond count1ChemAxon
refractivity64.88ChemAxon
polarizability25.89ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. 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
  2. Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] Pharmazie. 2000 Apr;55(4):293-6. Pubmed
  3. 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
  4. 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
ResourceLink
KEGG DrugD00268
PubChem Compound2717
PubChem Substance46505352
ChemSpider2616
ChEBI3619
ChEMBLCHEMBL1200714
Therapeutic Targets DatabaseDAP001252
PharmGKBPA448939
WikipediaChlormezanone
ATC CodesM03BB02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Translocator protein

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Translocator protein P30536 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 11, 2014 08:14