U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H19ClN4
Molecular Weight 326.823
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOZAPINE

SMILES

CN1CCN(CC1)C2=NC3=CC(Cl)=CC=C3NC4=CC=CC=C24

InChI

InChIKey=QZUDBNBUXVUHMW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Clozapine was discovered in 1958 by an anesthetist and now it is used for the treatment of schizophrenia. Although the exact mechanism of its action is unknown, the effect of clozapine on schizophrenia is associated with inhibition of dopamine D2 and serotonin 2A receptors.

CNS Activity

Approval Year

1989
74
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2205
Schizophrenia
 160.0 nM [Ki]
Antagonist
2205
Schizophrenia
 5.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Dopamine D2 receptor
Serotonin 2a (5-HT2a) receptor
Approved
7817
CLOZARIL
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
Antipsychotic medications and the elderly: effects on cognition and implications for use.
2001
Olanzapine: an updated review of its use in the management of schizophrenia.
2001
Protein thiol oxidation by haloperidol results in inhibition of mitochondrial complex I in brain regions: comparison with atypical antipsychotics.
2001 Apr
New onset diabetes and atypical antipsychotics.
2001 Feb
Bodyweight gain with atypical antipsychotics. A comparative review.
2001 Jan
Electroconvulsive therapy in rehabilitation: the Hong Kong experience.
2001 Mar
5-HT(2A) and D(2) receptor blockade increases cortical DA release via 5-HT(1A) receptor activation: a possible mechanism of atypical antipsychotic-induced cortical dopamine release.
2001 Mar
Atypical antipsychotics and hyperglycaemia.
2001 Mar
Clozapine and pulmonary embolus.
2001 Mar
Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?: A new hypothesis.
2001 Mar
Patents

Patents

JP2002511409A
21
JP2005528380A
6
JP2006505569A
63
JP2007514770A
70
JP2008528532A
12
JP2011526251A
110
JP2013544838A
2
JPH10175865A
4

Sample Use Guides

In Vivo Use Guide
Start with 12.5 mg once daily or twice daily, then increase the total daily dosage in increments of 25 mg to 50 mg per day (if well-tolerated) in order to reach 300 mg to 450 mg per day, in divided doses, by the end of 2 weeks.
Route of Administration: Oral
In Vitro Use Guide
The effects of antipsychotic medication on the energy metabolism of OLN-93 cells were analyzed by adding a vehicle (0.01% HCl, same dissolving solution used to solubilize the antipsychotics), 1 or 10 ug/ml of clozapine to the cell culture for 6 or 24 h.
Name Type Language
CLOZAPINE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
CLOZAPINE [WHO-DD]
Common Name English
CLOZAPINE [JAN]
Common Name English
LEPONEX
Brand Name English
8-CHLORO-11-(4-METHYL-1-PIPERAZINYL)-5H-DIBENZO(B,E)(1,4)DIAZEPINE
Systematic Name English
CLOZAPINE [MI]
Common Name English
CLOZAPINE (CLOZARIL) [VANDF]
Common Name English
CLOZAPINE (FAZACLO) [VANDF]
Common Name English
CLOZAPINE [USAN]
Common Name English
CLOZAPINE RESOLUTION MIXTURE [USP-RS]
Common Name English
CLOZARIL
Brand Name English
CLOZAPINE [HSDB]
Common Name English
HF-1854
Code English
FAZACLO
Brand Name English
CLOZAPINE [INN]
Common Name English
CLOZAPINE (VERSACLOZ) [VANDF]
Common Name English
CLOZAPINE RESOLUTION MIXTURE
USP-RS  
Common Name English
CLOZAPINE [EP]
Common Name English
CLOZAPINE (IVAX) [VANDF]
Common Name English
5H-DIBENZO(B,E)(1,4)DIAZEPINE, 8-CHLORO-11-(4-METHYL-1-PIPERAZINYL)-
Systematic Name English
CLOZAPINE [USP]
Common Name English
CLOZAPINE (CARACO) [VANDF]
Common Name English
HF 1854
Code English
CLOZAPINE (MYLAN) [VANDF]
Common Name English
CLOZAPINE [VANDF]
Common Name English
CLOZAPINE (UDL) [VANDF]
Common Name English
CLOZAPINE (TEVA) [VANDF]
Common Name English
CLOZAPINE [MART.]
Common Name English
CLOZAPINE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
LIVERTOX 230
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
NDF-RT N0000175430
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
WHO-VATC QN05AH02
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
WHO-ATC N05AH02
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
Code System Code Type Description
IUPHAR
38
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
EPA CompTox
5786-21-0
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
JAPANESE REVIEW
CLOZARIL
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY APPROVED APRIL 2009
MESH
D003024
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
LactMed
5786-21-0
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
MERCK INDEX
M3676
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY Merck Index
DRUG BANK
DB00363
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
HSDB
5786-21-0
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
CAS
1333667-72-3
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
ALTERNATIVE
WIKIPEDIA
CLOZAPINE
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
CAS
5786-21-0
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
INN
2612
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
EVMPD
SUB06787MIG
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
RXCUI
2626
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY RxNorm
ECHA (EC/EINECS)
227-313-7
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
ChEMBL
CHEMBL42
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
NCI_THESAURUS
C28936
Created by admin on Tue Mar 06 10:23:54 UTC 2018 , Edited by admin on Tue Mar 06 10:23:54 UTC 2018
PRIMARY
ACTIVE MOIETY
Structure of CLOZAPINE
METABOLITE ACTIVE (PARENT)
Structure of NORCLOZAPINE
METABOLITE LESS ACTIVE (PARENT)
Structure of CLOZAPINE N-OXIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966