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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GroupsApproved, Withdrawn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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
FenaprimNot Available
TrancopalWinthropSreon
Brand mixtures
Brand NameIngredients
MyoflexParacetamol + Chlormezanone
SaltsNot Available
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-1λ⁶,3-thiazinane-1,1,4-trione
SMILES
CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • 1,3-thiazinane
  • Aryl halide
  • Aryl chloride
  • Tertiary carboxylic acid amide
  • Sulfone
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9167
Blood Brain Barrier+0.9383
Caco-2 permeable-0.5597
P-glycoprotein substrateNon-substrate0.6347
P-glycoprotein inhibitor INon-inhibitor0.6885
P-glycoprotein inhibitor IINon-inhibitor0.9959
Renal organic cation transporterNon-inhibitor0.7164
CYP450 2C9 substrateNon-substrate0.6022
CYP450 2D6 substrateNon-substrate0.7983
CYP450 3A4 substrateSubstrate0.6616
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.9375
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5186
Ames testNon AMES toxic0.6263
CarcinogenicityNon-carcinogens0.7622
BiodegradationNot ready biodegradable0.6329
Rat acute toxicity2.6246 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9892
hERG inhibition (predictor II)Non-inhibitor0.7018
Pharmacoeconomics
ManufacturersNot Available
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 Solubility1.61 mg/mLALOGPS
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 Area54.45 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.88 m3·mol-1ChemAxon
Polarizability25.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS1D NMR
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
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