CHEBI:3766 - clozapine

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ChEBI Name clozapine
ChEBI ID CHEBI:3766
Definition A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H19ClN4
Net Charge 0
Average Mass 326.824
Monoisotopic Mass 326.130
InChI 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
InChIKey QZUDBNBUXVUHMW-UHFFFAOYSA-N
SMILES N1=C(C2=CC=CC=C2NC3=CC=C(C=C13)Cl)N4CCN(CC4)C
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
(via benzodiazepine )
Application(s): serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
second generation antipsychotic
Antipsychotic drugs which can have different modes of action but which tend to be less likely than first generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements.
GABA modulator
A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors appear to have at least three allosteric sites at which modulators act: a site at which benzodiazepines act by increasing the opening frequency of gamma-aminobutyric acid-activated chloride channels; a site at which barbiturates act to prolong the duration of channel opening; and a site at which some steroids may act.
(via benzodiazepine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing clozapine (CHEBI:3766) has role adrenergic antagonist (CHEBI:37887)
clozapine (CHEBI:3766) has role dopaminergic antagonist (CHEBI:48561)
clozapine (CHEBI:3766) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
clozapine (CHEBI:3766) has role environmental contaminant (CHEBI:78298)
clozapine (CHEBI:3766) has role GABA antagonist (CHEBI:65259)
clozapine (CHEBI:3766) has role histamine antagonist (CHEBI:37956)
clozapine (CHEBI:3766) has role muscarinic antagonist (CHEBI:48876)
clozapine (CHEBI:3766) has role second generation antipsychotic (CHEBI:65191)
clozapine (CHEBI:3766) has role serotonergic antagonist (CHEBI:48279)
clozapine (CHEBI:3766) has role xenobiotic (CHEBI:35703)
clozapine (CHEBI:3766) is a N-arylpiperazine (CHEBI:46848)
clozapine (CHEBI:3766) is a N-methylpiperazine (CHEBI:46920)
clozapine (CHEBI:3766) is a benzodiazepine (CHEBI:22720)
clozapine (CHEBI:3766) is a organochlorine compound (CHEBI:36683)
IUPAC Name
8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine
INNs Sources
clozapina ChEBI
clozapine ChEBI
clozapinum ChEBI
Synonyms Sources
Clozapin DrugBank
Clozapine KEGG COMPOUND
Database Links Databases
C06924 KEGG COMPOUND
Clozapine Wikipedia
D00283 KEGG DRUG
DB00363 DrugBank
FR1334944 Patent
HMDB14507 HMDB
NL293201 Patent
US3539573 Patent
View more database links
Registry Numbers Types Sources
0764984 Beilstein Registry Number Beilstein
5786-21-0 CAS Registry Number ChemIDplus
764984 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18690109 PubMed citation Europe PMC
18766167 PubMed citation Europe PMC
20825390 PubMed citation Europe PMC
24219174 PubMed citation Europe PMC
Last Modified
06 July 2016