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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:47 UTC
HMDB IDHMDB0014507
Secondary Accession Numbers
  • HMDB14507
Metabolite Identification
Common NameClozapine
DescriptionA tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent. [PubChem]
Structure
Data?1582753187
Synonyms
ValueSource
ClozapinChEBI
ClozapinaChEBI
ClozapinumChEBI
ClozarilKegg
LeponexHMDB
Chemical FormulaC18H19ClN4
Average Molecular Weight326.823
Monoisotopic Molecular Weight326.129824335
IUPAC Name6-chloro-10-(4-methylpiperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene
Traditional Nameclozapine
CAS Registry Number5786-21-0
SMILES
CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12
InChI Identifier
InChI=1S/C18H19ClN4/c1-22-8-10-23(11-9-22)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3
InChI KeyQZUDBNBUXVUHMW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzodiazepines. Dibenzodiazepines are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by diazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub ClassDibenzodiazepines
Direct ParentDibenzodiazepines
Alternative Parents
Substituents
  • Dibenzodiazepine
  • 1,4-benzodiazepine
  • N-methylpiperazine
  • N-alkylpiperazine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Imidolactam
  • Piperazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amidine
  • Secondary amine
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carboxylic acid amidine
  • Propargyl-type 1,3-dipolar organic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 - 184 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.19 g/LNot Available
LogP2.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM178.830932474
[M+H]+Not Available177.536http://allccs.zhulab.cn/database/detail?ID=AllCCS00000995
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP10(3.67) g/LALOGPS
logP10(3.4) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)15.9ChemAxon
pKa (Strongest Basic)7.35ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area30.87 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity97.36 m³·mol⁻¹ChemAxon
Polarizability35.77 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ClozapineCN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C124119.6Standard polar33892256
ClozapineCN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C122903.2Standard non polar33892256
ClozapineCN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C122885.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clozapine,1TMS,isomer #1CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC12802.3Semi standard non polar33892256
Clozapine,1TMS,isomer #1CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC12744.5Standard non polar33892256
Clozapine,1TMS,isomer #1CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C)C3=CC=CC=C23)CC13933.8Standard polar33892256
Clozapine,1TBDMS,isomer #1CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC12935.4Semi standard non polar33892256
Clozapine,1TBDMS,isomer #1CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC12955.4Standard non polar33892256
Clozapine,1TBDMS,isomer #1CN1CCN(C2=NC3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)CC14013.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clozapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r5-9064000000-0f31b1de88be42ac83812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clozapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-qTof , Positive-QTOFsplash10-00b9-0298000000-50d2ee0b52827fd1aee32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-qTof , Positive-QTOFsplash10-00di-2690000000-daaa74a4f85f5e8b59262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00di-0090000000-bc2ca4d5a76a5facf8972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-004i-0009000000-986bc19f7e7e8602d0052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00b9-0049000000-d6315d4aeb74c251e9392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00di-0090000000-27fd28450826291cc8c62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00di-0290000000-474b25ea27690471db0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-0006-0970000000-a58015260aaddb4245bd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-0006-0930000000-3ccfd048a34fdb4f594f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-004i-0009000000-7df53c42e3b1618bfdec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-004i-0049000000-7522cc8ebf988effc7922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00di-0090000000-bd138be4ae488c201ed32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00di-0190000000-68c8b78f304c38b7b7b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-0006-0980000000-a9dd724f32c02059c5102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-0006-0930000000-61c0f65f163824ddd5942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine LC-ESI-ITFT , positive-QTOFsplash10-00di-0090000000-da747a0572aa2c21683f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine , positive-QTOFsplash10-002f-0930000000-614883dbe075268cf23a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine , positive-QTOFsplash10-00b9-0298000000-50d2ee0b52827fd1aee32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clozapine , positive-QTOFsplash10-00di-2690000000-daaa74a4f85f5e8b59262017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clozapine 10V, Positive-QTOFsplash10-004i-0009000000-b771968b218f574a20312016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clozapine 20V, Positive-QTOFsplash10-004i-1049000000-24dab1e16fa5778e3f052016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clozapine 40V, Positive-QTOFsplash10-004i-2190000000-6b669cd26b101d106f1c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clozapine 10V, Negative-QTOFsplash10-004i-0009000000-178d40f752b4d092a8a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clozapine 20V, Negative-QTOFsplash10-004i-0029000000-5b7197f427b8cfdcdac22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clozapine 40V, Negative-QTOFsplash10-0006-4290000000-33f870d86d2adcc8f0492016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00363 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00363 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 IDDB00363
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10442628
KEGG Compound IDC06924
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClozapine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID3766
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. Vaddadi KS, Soosai E, Vaddadi G: Low blood selenium concentrations in schizophrenic patients on clozapine. Br J Clin Pharmacol. 2003 Mar;55(3):307-9. [PubMed:12630982 ]
  2. Alvir JM, Lieberman JA, Safferman AZ, Schwimmer JL, Schaaf JA: Clozapine-induced agranulocytosis. Incidence and risk factors in the United States. N Engl J Med. 1993 Jul 15;329(3):162-7. [PubMed:8515788 ]
  3. Lane HY, Chang YC, Chang WH, Lin SK, Tseng YT, Jann MW: Effects of gender and age on plasma levels of clozapine and its metabolites: analyzed by critical statistics. J Clin Psychiatry. 1999 Jan;60(1):36-40. [PubMed:10074876 ]
  4. Naheed M, Green B: Focus on clozapine. Curr Med Res Opin. 2001;17(3):223-9. [PubMed:11900316 ]