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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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,8-11H2,1H3InChIKey
QZUDBNBUXVUHMW-UHFFFAOYSA-NSmiles
CN1CCN(CC1)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.