Chlormezanone (T3D3009)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-21 20:28:33 UTC
Update Date2014-12-24 20:25:55 UTC
Accession NumberT3D3009
Identification
Common NameChlormezanone
ClassSmall Molecule
DescriptionChlormezanone is only found in individuals that have used or taken this drug. It is a non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm. [PubChem]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.
Compound Type
  • Amide
  • Amine
  • Anti-Anxiety Agent
  • Antipsychotic Agent
  • Benzodiazepine
  • Drug
  • Metabolite
  • Muscle Relaxant, Central
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(+-)-Chlormezanone
(±)-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
Chlormethazone
Chlormezanon
Chlormezanona
Chlormezanonum
Clormetazanone
Clormetazon
Clormezanona
Clormezanone
Dichloromethazanone
Dichloromezanone
Dl-Chlormezanone
Fenaprim
Trancopal
Chemical FormulaC11H12ClNO3S
Average Molecular Mass273.736 g/mol
Monoisotopic Mass273.023 g/mol
CAS Registry Number80-77-3
IUPAC Name2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione
Traditional Name2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione
SMILESCN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
InChI IdentifierInChI=1/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
InChI KeyInChIKey=WEQAYVWKMWHEJO-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes 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
  • Aryl chloride
  • Aryl halide
  • 1,3-thiazinane
  • Sulfone
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point116.2-118.6°C
Boiling PointNot Available
Solubility2500 mg/L (at 25°C)
LogP1.3
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP0.84ALOGPS
logP0.92ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)19.07ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area54.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.88 m³·mol⁻¹ChemAxon
Polarizability25.72 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fi0-3900000000-5e5d0d06b736cd6e312d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0kmi-0690000000-1392c5b54088e4de1cda2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kmi-0690000000-1392c5b54088e4de1cda2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00e9-9800000000-6a7c54ed417bbe3bf39c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a59-0980000000-f53a3c2f328bf92ecea22021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-3920000000-72d4eeb6dec00afcf7142021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00di-9000000000-6d971fd886764cbe9edc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00e9-9800000000-160e4ad7fa10bdfbce0e2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1390000000-8bee31987cb996a6941d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3290000000-fe5427b04dacecf713b82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8900000000-d26b01b91b77c8ccf5ff2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-13d72ad524b7d05b5dd42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1920000000-f5d97bfa6c8356b4baf42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-7900000000-66d56cc398b6ac3900a02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-fd587e06fea093c002172021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0910000000-d1589364a7086eeb574d2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-2900000000-941a0471defcde1f16b62021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-0ebbdf325da9547d6d6a2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-1390000000-fb20b8fdbf901e9ead652021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-9160000000-435ff6a491b5b8c517962021-10-11View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-7900000000-6c729f1a3c9cb4241b452014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityChlormezanone 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.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the management of anxiety and in the treatment of muscle spasm.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include drowsiness, weakness, nausea, dizziness, abdominal pain, cerebral oedema and renal tubular necrosis, hyperglycaemia and hypoglycaemia, liver damage, encephalopathy, coma and death.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01178
HMDB IDHMDB15309
PubChem Compound ID2717
ChEMBL IDCHEMBL1200714
ChemSpider ID2616
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID3619
BioCyc IDNot Available
CTD IDNot Available
Stitch IDChlormezanone
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkChlormezanone
References
Synthesis ReferenceNot Available
MSDST3D3009.pdf
General References
  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. [15897685 ]
  2. Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]. Pharmazie. 2000 Apr;55(4):293-6. [10798243 ]
  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. [9770210 ]
  4. Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers]. Therapie. 1990 Jul-Aug;45(4):315-9. [2399514 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Translocator protein
General Function:
Cholesterol binding
Specific 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).
Gene Name:
TSPO
Uniprot ID:
P30536
Molecular Weight:
18827.81 Da
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. [17139284 ]
  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. [17016423 ]