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Substance Name: Perphenazine [USP:INN:BAN:JAN]
RN: 58-39-9
UNII: FTA7XXY4EZ
InChIKey: RGCVKNLCSQQDEP-UHFFFAOYSA-N

Note

  • An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.

Molecular Formula

  • C21-H26-Cl-N3-O-S

Molecular Weight

  • 403.9754
 

Classification Codes

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

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Perphenazine

Synonyms

  • 1',1-(2-Idrossietil)-4,3-(2-cloro-10-fenotiazil)propilpiperazina
  • 1',1-(2-Idrossietil)-4,3-(2-cloro-10-fenotiazil)propilpiperazina [Italian]
  • 1-(2-Hydroxyethyl)-4-(3-(2-chloro-10-phenothiazinyl)propyl)piperazine
  • 1-Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-
  • 1-Piperazineethanol, 4-(3-(2-chlorophenothiazin-10-yl)propyl)-
  • 2-Chloro-10-(3-(1-(2-hydroxyethyl)-4-piperazinyl)propyl)phenothiazine
  • 2-Chloro-10-3-(1-(2-hydroxyethyl)-4-piperazinyl)propyl phenothiazine
  • 4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol
  • AI3-50151
  • Chlorperphenazine
  • Chlorpiprazine
  • Decentan
  • EINECS 200-381-5
  • Emesinal
  • Etaperazin
  • Etaperazine
  • Ethaperazine
  • F-mon
  • Fentazin
  • gamma-(4-(beta-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine
  • HSDB 3379
  • NSC 150866
  • Perfenazina
  • Perfenazina [INN-Spanish]
  • Perfenazina [Italian]
  • Perfenazine
  • Perphenan
  • Perphenazin
  • Perphenazine
  • Perphenazinum
  • Perphenazinum [INN-Latin]
  • Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-
  • PZC
  • Sch 3940
  • Thilatazin
  • Tranquisan
  • Trifaron
  • Trilafon
  • Trilifan
  • Triphenot
  • UNII-FTA7XXY4EZ

Systematic Names

  • 1-Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-
  • 1-Piperazineethanol, 4-(3-(2-chlorophenothiazin-10-yl)propyl)-
  • Perphenazine
  • Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-

Mixture Names

  • Etrafon
  • Triavil

Registry Numbers

CAS Registry Number

  • 58-39-9

FDA UNII

  • FTA7XXY4EZ

System Generated Number

  • 0000058399

Structure Descriptors

InChI

1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2

InChIKey

RGCVKNLCSQQDEP-UHFFFAOYSA-N

Smiles

c1ccc2c(c1)N(c3cc(ccc3S2)Cl)CCCN4CCN(CC4)CCO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 32mg/kg (32mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
cat LD50 intravenous 35mg/kg (35mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
cat LD50 subcutaneous > 2500ug/kg (2.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
cat LDLo oral 1gm/kg (1000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
dog LD50 intravenous 51mg/kg (51mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: REGIDITY		 Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
dog LD50 subcutaneous > 20mg/kg (20mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
human TDLo intramuscular 71428ng/kg (0.071428mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) British Medical Journal. Vol. 3, Pg. 867, 1967.
monkey LD50 subcutaneous > 510ug/kg (0.51mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 intraperitoneal 64mg/kg (64mg/kg)   Journal of Pharmaceutical Sciences. Vol. 59, Pg. 976, 1970.
mouse LD50 intravenous 19mg/kg (19mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY		 Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 oral 120mg/kg (120mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 185, 1973.
mouse LD50 subcutaneous > 80mg/kg (80mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
pigeon LD50 intramuscular 250mg/kg (250mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE		 Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
pigeon LD50 intravenous 32mg/kg (32mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE		 Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
rat LD50 intraperitoneal 146mg/kg (146mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 917, 1974.
rat LD50 intravenous 34mg/kg (34mg/kg)   Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
rat LD50 oral 318mg/kg (318mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
rat LD50 subcutaneous > 80mg/kg (80mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 97 deg C   EXP
pKa Dissociation Constant 7.94 (none)   EXP
log P (octanol-water) 4.2 (none)   EXP
Water Solubility 28.3 mg/L 24 EXP
Vapor Pressure 2.84E-13 mm Hg 25 EST
Henry's Law Constant 5.19E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.66E-10 cm3/molecule-sec 25 EST

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