Clozapine

Clozapine

Clinical data
Trade names	Clozaril, FazaClo, Versacloz
AHFS/Drugs.com	Monograph
MedlinePlus	a691001
Pregnancy category	AU: C US: B (No risk in non-human studies)
Routes of administration	Oral
ATC code	N05AH02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	60 to 70%
Metabolism	Liver, by several isozymes
Biological half-life	6 to 26 hours (mean value 14.2 hours in steady state conditions)
Excretion	80% in metabolized state: 30% biliary and 50% kidney
Identifiers
IUPAC name 8-Chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine
CAS Number	5786-21-0 Y
PubChem CID	2818
IUPHAR/BPS	38
DrugBank	DB00363 Y
ChemSpider	10442628 Y
UNII	J60AR2IKIC
KEGG	D00283 Y
ChEBI	CHEBI:3766 Y
ChEMBL	CHEMBL42 Y
ECHA InfoCard	100.024.831
Chemical and physical data
Formula	C18H19ClN4
Molar mass	326.83 g·mol−1
3D model (Jmol)	Interactive image
Melting point	183 °C (361 °F)
Solubility in water	0.1889 mg/mL (20 °C)
SMILES CN1CCN(CC1)C2=Nc3cc(ccc3Nc4c2cccc4)Cl
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 Y Key:QZUDBNBUXVUHMW-UHFFFAOYSA-N Y

Clozapine, sold under the brand name Clozaril among others, is an atypical antipsychotic medication. It is mainly used for schizophrenia that does not improve following the use of other antipsychotic medications. In those with schizophrenia and schizoaffective disorder it may decrease the rate of suicidal behavior. It is possibly more effective than typical antipsychotics and in those who are treatment resistant. It is taken by mouth. Clozapine is associated with a relatively high risk of low white blood cells which may result in death. To decrease this risk it is recommended that the blood be regularly monitored. Other serious risks include seizures, inflammation of the heart, high blood sugar levels, and in older people with psychosis as a result of dementia an increased risk of death. Common side effects include drowsiness, dry mouth, low blood pressure, trouble seeing, and dizziness. The potentially permanent movement disorder tardive dyskinesia occurs in about 5% of people. Its mechanism of action is not entirely clear.

Clozapine was first made in 1958 and sold commercially in 1972. It was the first atypical antipsychotic. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is between 0.05 and 2.10 USD per day as of 2014.