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Substance Name: Clozapine [USAN:USP:INN:BAN]
RN: 5786-21-0
UNII: J60AR2IKIC
InChIKey: QZUDBNBUXVUHMW-UHFFFAOYSA-N

Note

  • A 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.

Molecular Formula

  • C18-H19-Cl-N4

Molecular Weight

  • 326.8291
 

Classification Codes

  • Antipsychotic
  • Antipsychotic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • GABA Agents
  • GABA Antagonists
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Serotonin Agents
  • Serotonin Antagonists
  • Tranquilizing Agents

Names and Synonyms

Name of Substance

  • Clozapine
  • Clozapine [USAN:USP:INN:BAN]

MeSH Heading

  • Clozapine

Synonyms

  • 5-25-11-00364 (Beilstein Handbook Reference)
  • 5H-Dibenzo(b,e)(1,4)diazepine, 8-chloro-11-(4-methyl-1-piperazinyl)-
  • 8-Chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine
  • BRN 0764984
  • CCRIS 9171
  • Clorazil
  • Clozapin
  • Clozapina
  • Clozapina [INN-Spanish]
  • Clozapine
  • Clozapinum
  • Clozapinum [INN-Latin]
  • Clozaril
  • EINECS 227-313-7
  • Fazaclo
  • Fazaclo ODT
  • HF 1854
  • HF-1854
  • HSDB 6478
  • Iprox
  • Leponex
  • LX 100-129
  • UNII-J60AR2IKIC
  • Versacloz
  • W-801

Systematic Names

  • 5H-Dibenzo(b,e)(1,4)diazepine, 8-chloro-11-(4-methyl-1-piperazinyl)-
  • Clozapine

Registry Numbers

CAS Registry Number

  • 5786-21-0

FDA UNII

  • J60AR2IKIC

System Generated Number

  • 0005786210

Structure Descriptors

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

CN1CCN(CC1)C2=Nc3cc(ccc3Nc4c2cccc4)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 4762ug/kg (4.762mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ANTIPSYCHOTIC
American Journal of Emergency Medicine. Vol. 14, Pg. 462, 1996.
dog LD50 oral 145mg/kg (145mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
guinea pig LD50 oral 510mg/kg (510mg/kg)   Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
human TDLo oral 5mg/kg/7D-I (5mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 919, 1972.
man TDLo oral 4286ug/kg/11D (4.286mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
Journal of Clinical Pyschopharmacology. Vol. 13, Pg. 155, 1993.
man TDLo oral 5357ug/kg/5D- (5.357mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: ANTIPSYCHOTIC

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Journal of Clinical Pyschopharmacology. Vol. 12, Pg. 139, 1992.
man TDLo oral 27mg/kg/13D-I (27mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)"
Journal of Clinical Psychiatry. Vol. 55, Pg. 38, 1994.
man TDLo oral 40mg/kg (40mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Veterinary and Human Toxicology. Vol. 41, Pg. 20, 1999.
man TDLo oral 86mg/kg/15D-I (86mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
British Journal of Psychiatry. Vol. 173, Pg. 440, 1998.
man TDLo oral 270mg/kg/6W-I (270mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BLOOD: AGRANULOCYTOSIS

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
Annales de Medecine Interne. Vol. 144, Pg. 494, 1993.
man TDLo oral 429mg/kg/60D- (429mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) American Journal of Psychiatry. Vol. 152, Pg. 649, 1995.
man TDLo oral 429mg/kg (429mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 325, 2000.
man TDLo oral 2211mg/kg/37W (2211mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" Journal of Clinical Pyschopharmacology. Vol. 15, Pg. 287, 1995.
man TDLo oral 3280mg/kg/82W (3280mg/kg) BLOOD: AGRANULOCYTOSIS American Journal of Psychiatry. Vol. 153, Pg. 1503, 1996.
mouse LD50 intraperitoneal 90mg/kg (90mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
mouse LD50 intravenous 36500ug/kg (36.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 667, 1973.
mouse LD50 oral 150mg/kg (150mg/kg)   Journal of Medicinal Chemistry. Vol. 23, Pg. 878, 1980.
mouse LD50 subcutaneous 194mg/kg (194mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 667, 1973.
rat LD50 intramuscular 210mg/kg (210mg/kg)   Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
rat LD50 intravenous 41600ug/kg (41.6mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 667, 1973.
rat LD50 oral 251mg/kg (251mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 667, 1973.
rat LD50 subcutaneous 240mg/kg (240mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 667, 1973.
women TDLo oral 20mg/kg (20mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

BLOOD: LEUKOPENIA

BEHAVIORAL: COMA
Annals of Internal Medicine. Vol. 121, Pg. 722, 1994.
women TDLo oral 28mg/kg/2W-I (28mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS Lancet. Vol. 340, Pg. 251, 1992.
women TDLo oral 96mg/kg/48D-I (96mg/kg) BLOOD: AGRANULOCYTOSIS

BLOOD: LEUKOPENIA
Human Psychopharmacology. Vol. 13, Pg. 583, 1998.
women TDLo oral 104mg/kg/26D- (104mg/kg) BLOOD: EOSINOPHILIA Journal of Clinical Psychiatry. Vol. 59, Pg. 195, 1998.
women TDLo oral 168mg/kg/4W-I (168mg/kg) BLOOD: AGRANULOCYTOSIS Netherlands Journal of Medicine. Vol. 52, Pg. 26, 1998.
women TDLo oral 280mg/kg/5W-I (280mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

BLOOD: EOSINOPHILIA
American Journal of Psychiatry. Vol. 150, Pg. 985, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 183-184 deg C   EXP
pKa Dissociation Constant 7.5 (none)   EXP
log P (octanol-water) 3.23 (none)   EXP
Water Solubility 11.8 mg/L 25 EST
Vapor Pressure 9.48E-09 mm Hg 25 EST
Henry's Law Constant 9.29E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.76E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.