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Substance Name: Chlorpromazine [USP:INN:BAN]
RN: 50-53-3
UNII: U42B7VYA4P
InChIKey: ZPEIMTDSQAKGNT-UHFFFAOYSA-N

Note

  • The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.

Molecular Formula

  • C17-H19-Cl-N2-S

Molecular Weight

  • 318.8701
 

Classification Codes

  • Anti-Emetic
  • Antiemetics
  • Antipsychotic
  • Antipsychotic Agents
  • Autonomic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Dopamine Agents
  • Dopamine Antagonists
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Tranquilizing Agents

Names and Synonyms

Name of Substance

  • Chlorpromazine
  • Chlorpromazine [USP:INN:BAN]

MeSH Heading

  • Chlorpromazine

Synonyms

  • 2-Chloro-10-(3-(dimethylamino)propyl)phenothiazine
  • 2-Chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine
  • 2-Chloropromazine
  • 2-Cloro-10 (3-dimetilaminopropil)fenotiazina
  • 2-Cloro-10 (3-dimetilaminopropil)fenotiazina [Italian]
  • 4560 R.P.
  • Aminazin
  • Aminazine
  • Ampliactil
  • BC 135
  • CCRIS 3711
  • Chlor-Promanyl
  • Chlorderazin
  • Chloro-3 (dimethylamino-3 propyl)-10 phenothiazine
  • Chloro-3 (dimethylamino-3 propyl)-10 phenothiazine [French]
  • Chloropromazine
  • Chlorpromados
  • Chlorpromazin
  • Chlorpromazine
  • Chlorpromazinum
  • Chlorpromazinum [INN-Latin]
  • Clorpromazina
  • Clorpromazina [INN-Spanish]
  • Clorpromazina [Italian]
  • Contomin
  • CPZ
  • EINECS 200-045-8
  • Elmarin
  • Esmind
  • Fenactil
  • Fenaktyl
  • Fraction AB
  • GG 407
  • HL 5746
  • HSDB 3033
  • Largactil
  • Largactilothiazine
  • Largactyl
  • Megaphen
  • N-(3-Dimethylaminopropyl)-3-chlorophenothiazine
  • Novomazina
  • NSC 167745
  • Phenactyl
  • Proma
  • Promactil
  • Promazil
  • Propaphenin
  • Prozil
  • Psychozine
  • Sanopron
  • SKF 2601-A
  • Thorazine
  • Thorazine Suppositories
  • Torazina
  • UNII-U42B7VYA4P
  • Wintermin

Systematic Names

  • 10H-Phenothiazine-10-propanamine, 2-chloro-N,N-dimethyl-
  • Chlorpromazine
  • Phenothiazine, 2-chloro-10-(3-(dimethylamino)propyl)-

Mixture Name

  • Chlorpromazine

Registry Numbers

CAS Registry Number

  • 50-53-3

FDA UNII

  • U42B7VYA4P

System Generated Number

  • 0000050533

Structure Descriptors

InChI

InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3

InChIKey

ZPEIMTDSQAKGNT-UHFFFAOYSA-N

Smiles

CN(C)CCCN1c2ccccc2Sc3ccc(Cl)cc13

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous > 10mg/kg (10mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
cat LDLo oral 100mg/kg (100mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
child LDLo oral 37500ug/kg (37.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA		 New England Journal of Medicine. Vol. 256, Pg. 527, 1957.
dog LD50 intravenous 30mg/kg (30mg/kg) BLOOD: HEMORRHAGE

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: EMPHYSEMA		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 118, Pg. 358, 1959.
dog LD50 subcutaneous > 20mg/kg (20mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
dog LDLo oral 250mg/kg (250mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: REGIDITY		 Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
guinea pig LD50 intraperitoneal 87mg/kg (87mg/kg)   Medicina Experimentalis. Vol. 8, Pg. 237, 1963.
guinea pig LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
human TDLo oral 8570ug/kg/12D (8.57mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: TREMOR

BEHAVIORAL: WAKEFULNESS		 Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 93, 1972.
infant TDLo oral 20mg/kg (20mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION		 American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
mammal (species unspecified) LD50 oral 500mg/kg (500mg/kg) BEHAVIORAL: ANTICONVULSANT

BEHAVIORAL: ALTERATION OF CLASSICAL CONDITIONING		 Journal of Medicinal Chemistry. Vol. 8, Pg. 836, 1965.
man TDLo oral 8900ug/kg (8.9mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA American Journal of Emergency Medicine. Vol. 14, Pg. 467, 1996.
man TDLo oral 217mg/kg/19D (217mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BLOOD: AGRANULOCYTOSIS		 Journal of Clinical Psychiatry. Vol. 46, Pg. 341, 1985.
monkey LD50 subcutaneous > 5mg/kg (5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LC50 inhalation 209mg/m3/2H (209mg/m3) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: MUSCLE WEAKNESS

BLOOD: LEUKOPENIA		 Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 10, Pg. 73, 1968.
mouse LD50 intraperitoneal 14mg/kg (14mg/kg)   Farmaco, Edizione Scientifica. Vol. 14, Pg. 269, 1959.
mouse LD50 intravenous 16mg/kg (16mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY		 Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 oral 135mg/kg (135mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 118, Pg. 358, 1959.
mouse LD50 subcutaneous 33mg/kg (33mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: ATAXIA		 Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 unreported 82500ug/kg (82.5mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
mouse LDLo intramuscular 300mg/kg (300mg/kg)   Therapie. Vol. 15, Pg. 1064, 1960.
rabbit LD50 intravenous 16mg/kg (16mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959.
rat LC50 inhalation 209mg/m3/2H (209mg/m3) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BLOOD: LEUKOPENIA

BEHAVIORAL: MUSCLE WEAKNESS		 Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 10, Pg. 73, 1968.
rat LD50 intraperitoneal 137mg/kg (137mg/kg)   German Offenlegungsschrift Patent Document. Vol. #2350222,
rat LD50 intravenous 23mg/kg (23mg/kg)   Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
rat LD50 oral 142mg/kg (142mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 261, 1968.
rat LD50 subcutaneous 75mg/kg (75mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960.
women TDLo oral 200ug/kg (0.2mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BEHAVIORAL: SLEEP		 New York State Journal of Medicine. Vol. 57, Pg. 1922, 1957.
women TDLo oral 16800ug/kg/3W (16.8mg/kg) BLOOD: AGRANULOCYTOSIS Postgraduate Medical Journal. Vol. 69, Pg. 885, 1993.
women TDLo oral 166mg/kg/18D- (166mg/kg) BLOOD: OTHER CHANGES

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA		 Postgraduate Medical Journal. Vol. 53, Pg. 278, 1977.
women TDLo oral 240mg/kg/30D- (240mg/kg) BLOOD: AGRANULOCYTOSIS

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT		 Journal of Clinical Psychiatry. Vol. 46, Pg. 341, 1985.
women TDLo oral 240mg/kg/30D (240mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BLOOD: AGRANULOCYTOSIS		 Journal of Clinical Psychiatry. Vol. 46, Pg. 341, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
pKa Dissociation Constant 9.3 (none) 25 EXP
log P (octanol-water) 5.41 (none)   EXP
Water Solubility 2.55 mg/L 24 EXP
Vapor Pressure 1.77E-07 mm Hg 25 EST
Henry's Law Constant 3.95E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.45E-10 cm3/molecule-sec 25 EST

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