|
|
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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anti-Emetic
- Antiemetics
- Antipsychotic
- Antipsychotic Agents
- Antiviral (COVID-19)
- 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
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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,5,10-11H2,1-2H3InChIKey
ZPEIMTDSQAKGNT-UHFFFAOYSA-NSmiles
CN(C)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.