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Substance Name: Prochlorperazine [USP:INN:BAN:JAN]
RN: 58-38-8
UNII: YHP6YLT61T
InChIKey: WIKYUJGCLQQFNW-UHFFFAOYSA-N

Note

  • A phenothiazine antipsychotic used principally in the treatment of NAUSEA; VOMITING; and VERTIGO. It is more likely than CHLORPROMAZINE to cause EXTRAPYRAMIDAL DISORDERS. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612)

Molecular Formula

  • C20-H24-Cl-N3-S

Molecular Weight

  • 373.9496
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Prochlorperazine
  • Prochlorperazine [USP:INN:BAN:JAN]

MeSH Heading

  • Prochlorperazine

Synonyms

  • 10H-Phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-
  • 2-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-phenothiazine
  • 2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-10H-phenothiazine
  • 2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine
  • 3-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine
  • 3-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine
  • 6140 RP
  • Bayer A 173
  • Capazine
  • Chlormeprazine
  • Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazine
  • Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazine [French]
  • Chlorperazine
  • Compazine
  • Compazine Suppositories
  • COMPRO
  • EINECS 200-379-4
  • Emelent
  • HSDB 3171
  • Kronocin
  • Meterazin
  • Meterazine
  • N-(gamma-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazine
  • Nipodal
  • Novamin
  • Phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-
  • Prochlorperazin
  • Prochlorperazine
  • Prochlorperazinum
  • Prochlorperazinum [INN-Latin]
  • Prochlorpermazine
  • Prochlorpromazine
  • Procloperazine
  • Proclorperazina
  • Proclorperazina [INN-Spanish]
  • Proclorperazine
  • RP 6140
  • SKF 4657
  • Stemetil
  • Tementil
  • Temetid
  • UNII-YHP6YLT61T

Systematic Names

  • 10H-Phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-
  • Phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-
  • Prochlorperazine

Mixture Name

  • Eskatrol

Registry Numbers

CAS Registry Number

  • 58-38-8

FDA UNII

  • YHP6YLT61T

System Generated Number

  • 0000058388

Structure Descriptors

InChI

1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3

InChIKey

WIKYUJGCLQQFNW-UHFFFAOYSA-N

Smiles

CN1CCN(CC1)CCCN2c3ccccc3Sc4c2cc(cc4)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 2mg/kg/24H-I (2mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Annals of Emergency Medicine. Vol. 30, Pg. 234, 1997.
dog LDLo intravenous 100mg/kg (100mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 213, 1973.
dog LDLo oral 102mg/kg (102mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 213, 1973.
human TDLo oral 560ug/kg/10H- (0.56mg/kg) BEHAVIORAL: HEADACHE

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
New England Journal of Medicine. Vol. 312, Pg. 1125, 1985.
mouse LD50 intraperitoneal 120mg/kg (120mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 152, Pg. 1371, 1958.
mouse LD50 intravenous 85mg/kg (85mg/kg)   Cesko-Slovenska Farmacie. Vol. 16, Pg. 255, 1967.
mouse LD50 oral 400mg/kg (400mg/kg)   Drugs in Japan Vol. 6, Pg. 722, 1982.
mouse LD50 subcutaneous 350mg/kg (350mg/kg)   Psychopharmacologia Vol. 2, Pg. 209, 1961.
rabbit LD50 intravenous > 5mg/kg (5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959.
rat LD50 intraperitoneal 400mg/kg (400mg/kg)   Farmakologiya i Toksikologiya Vol. 24, Pg. 136, 1961.
rat LD50 intravenous > 20mg/kg (20mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 120, Pg. 450, 1959.
rat LD50 oral 1800mg/kg (1800mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 213, 1973.
women TDLo multiple routes 800ug/kg/4D-I (0.8mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Annals of Internal Medicine. Vol. 52, Pg. 538, 1960.
women TDLo oral 4500ug/kg/3D- (4.5mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
British Journal of Clinical Practice. Vol. 28, Pg. 201, 1974.
women TDLo unreported 1800ug/kg/2D- (1.8mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Annals of Internal Medicine. Vol. 52, Pg. 538, 1960.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 228 deg C   EXP
pKa Dissociation Constant 8.1 (none)   EXP
log P (octanol-water) 4.88 (none)   EXP
Water Solubility 15 mg/L 24 EXP
Vapor Pressure 2.73E-09 mm Hg 25 EST
Henry's Law Constant 1.07E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.52E-10 cm3/molecule-sec 25 EST

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