clozapine   Click here for help

GtoPdb Ligand ID: 38

Synonyms: Clorazil® | HF-1854
Approved drug
clozapine is an approved drug (FDA (1989))
Compound class: Synthetic organic
Comment: Note that PubChem CID 2818 has different double bond structure on the central heptane ring which results in a different InChIKey. Our structure is an exact match for the chemical structure in the INN record for this compound.

The major active metabolite of clozapine is N-desmethylclozapine.
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View more information in the IUPHAR Pharmacology Education Project: clozapine

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 30.87
Molecular weight 326.13
XLogP 3.86
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCN(CC1)C1=Nc2cc(Cl)ccc2Nc2c1cccc2
Isomeric SMILES CN1CCN(CC1)C1=Nc2cc(Cl)ccc2Nc2c1cccc2
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
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Summary of Clinical Use Click here for help
Antipsychotic agent used in the treatment of treatment resistant schizophrenia. This drug may also be used to reduce suicide risk in psychotic patients (US) and for the treatment of psychosis in Parkinson's disease (Europe)
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Clozapine is a selective monoaminergic antagonist, whose actions arise predominantly through high affinity interactions with serotonin 5HT2 receptors, dopamine D2 receptors, α1- and α2-adrenoceptors, and histamine H1 receptors. Antagonistic effects at D2 receptors in the mesolimbic pathway and 5-HT2A receptors in the frontal cortex likely contribute to the antipsychotic action of clozapine in schizophrenia patients.