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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:43:37 UTC
HMDB IDHMDB0015309
Secondary Accession Numbers
  • HMDB15309
Metabolite Identification
Common NameChlormezanone
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.
Structure
Data?1582753281
Synonyms
ValueSource
(+-)-ChlormezanoneChEBI
2-(p-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxideChEBI
2-(p-Chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxideChEBI
ChlormethazanoneChEBI
ChlormezanonaChEBI
ChlormezanonumChEBI
TrancopalKegg
ChlormethazoneHMDB
ChlormezanonHMDB
ClormetazanoneHMDB
ClormetazonHMDB
ClormezanoneHMDB
DichloromethazanoneHMDB
DichloromezanoneHMDB
DL-ChlormezanoneHMDB
Chemical FormulaC11H12ClNO3S
Average Molecular Weight273.736
Monoisotopic Molecular Weight273.022641652
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
CAS Registry Number80-77-3
SMILES
CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
InChI Identifier
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
InChI KeyWEQAYVWKMWHEJO-UHFFFAOYSA-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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point116.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.61 g/LNot Available
LogP1.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available158.198http://allccs.zhulab.cn/database/detail?ID=AllCCS00000870
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP10(0.84) g/LALOGPS
logP10(0.92) g/LChemAxon
logS10(-2.2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlormezanoneCN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O3253.9Standard polar33892256
ChlormezanoneCN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O2158.1Standard non polar33892256
ChlormezanoneCN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O2272.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chlormezanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fi0-3900000000-5e5d0d06b736cd6e312d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlormezanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-7900000000-6c729f1a3c9cb4241b452014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone LC-ESI-qTof , Positive-QTOFsplash10-0kmi-0690000000-1392c5b54088e4de1cda2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone , positive-QTOFsplash10-0kmi-0690000000-1392c5b54088e4de1cda2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone 45V, Positive-QTOFsplash10-00e9-9800000000-6a7c54ed417bbe3bf39c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone 15V, Negative-QTOFsplash10-0a59-0980000000-f53a3c2f328bf92ecea22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone 30V, Negative-QTOFsplash10-001i-3920000000-72d4eeb6dec00afcf7142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone 60V, Negative-QTOFsplash10-00di-9000000000-6d971fd886764cbe9edc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlormezanone 45V, Negative-QTOFsplash10-00e9-9800000000-160e4ad7fa10bdfbce0e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 10V, Positive-QTOFsplash10-00di-1390000000-8bee31987cb996a6941d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 20V, Positive-QTOFsplash10-00di-3290000000-fe5427b04dacecf713b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 40V, Positive-QTOFsplash10-0006-8900000000-d26b01b91b77c8ccf5ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 10V, Negative-QTOFsplash10-00di-0290000000-13d72ad524b7d05b5dd42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 20V, Negative-QTOFsplash10-0udi-1920000000-f5d97bfa6c8356b4baf42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 40V, Negative-QTOFsplash10-0a4r-7900000000-66d56cc398b6ac3900a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 10V, Positive-QTOFsplash10-00di-0090000000-fd587e06fea093c002172021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 20V, Positive-QTOFsplash10-0ufr-0910000000-d1589364a7086eeb574d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 40V, Positive-QTOFsplash10-0uxr-2900000000-941a0471defcde1f16b62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 10V, Negative-QTOFsplash10-00di-0090000000-0ebbdf325da9547d6d6a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 20V, Negative-QTOFsplash10-03k9-1390000000-fb20b8fdbf901e9ead652021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlormezanone 40V, Negative-QTOFsplash10-01q9-9160000000-435ff6a491b5b8c517962021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01178 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01178 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01178
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2616
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlormezanone
METLIN IDNot Available
PubChem Compound2717
PDB IDNot Available
ChEBI ID3619
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers]. Therapie. 1990 Jul-Aug;45(4):315-9. [PubMed:2399514 ]
  2. 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:9770210 ]
  3. Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]. Pharmazie. 2000 Apr;55(4):293-6. [PubMed:10798243 ]
  4. 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:15897685 ]

Enzymes

General function:
Signal transduction mechanisms
Specific function:
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. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
Gene Name:
TSPO
Uniprot ID:
P30536
Molecular weight:
18778.7
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: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. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]