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Substance Name: Pimozide [USAN:USP:INN:BAN:JAN]
RN: 2062-78-4
UNII: 1HIZ4DL86F
InChIKey: YVUQSNJEYSNKRX-UHFFFAOYSA-N

Note

  • A diphenylbutylpiperidine that is effective as an antipsychotic agent and as an alternative to HALOPERIDOL for the suppression of vocal and motor tics in patients with Tourette syndrome. Although the precise mechanism of action is unknown, blockade of postsynaptic dopamine receptors has been postulated. (From AMA Drug Evaluations Annual, 1994, p403).

Molecular Formula

  • C28-H29-F2-N3-O

Molecular Weight

  • 461.5531
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antipsychotic
  • Antipsychotic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Dopamine Agents
  • Dopamine Antagonists
  • Drug / Therapeutic Agent
  • Human Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Tranquilizing Agents
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Names and Synonyms

Name of Substance

  • Pimozide
  • Pimozide [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Pimozide

Synonyms

  • 1-(1-(4,4-Bis(p-fluorophenyl)butyl)-4-piperidyl)-2-benzimidazolinone
  • 1-(4,4-Bis(p-fluorophenyl)butyl)-4-(2-oxo-1-benzimidazolinyl)piperidine
  • 2H-Benzimidazol-2-one, 1-(1-(4,4-bis(4-fluorophenyl)butyl)-4-piperidinyl)-1,3-dihydro-
  • 5-24-02-00367 (Beilstein Handbook Reference)
  • BRN 0729089
  • CCRIS 9172
  • EINECS 218-171-7
  • McN-JR-6238
  • NSC 170984
  • Opiran
  • Orap
  • Pimozide
  • Pimozidum
  • Pimozidum [INN-Latin]
  • Primozida
  • Primozida [INN-Spanish]
  • R 6238
  • UNII-1HIZ4DL86F

Systematic Names

  • 2H-Benzimidazol-2-one, 1-(1-(4,4-bis(4-fluorophenyl)butyl)-4-piperidinyl)-1,3-dihydro-
  • Pimozide

Superlist Name

  • Pimozide

Registry Numbers

CAS Registry Number

  • 2062-78-4

FDA UNII

  • 1HIZ4DL86F

System Generated Number

  • 0002062784

Structure Descriptors

InChI

InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)

InChIKey

YVUQSNJEYSNKRX-UHFFFAOYSA-N

Smiles

Fc1ccc(cc1)C(CCCN2CCC(CC2)N3C(=O)Nc4ccccc34)c5ccc(F)cc5

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 32mg/kg (32mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 5, Pg. 106, 1974.
dog LD50 oral 40mg/kg (40mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 261, 1968.
guinea pig LD50 oral 189mg/kg (189mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR		 Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 261, 1968.
man TDLo oral 7714ug/kg/15W (7.714mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FLUID INTAKE

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED		 Journal of Clinical Pyschopharmacology. Vol. 12, Pg. 140, 1992.
mouse LD50 intraperitoneal 1070mg/kg (1070mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 5, Pg. 106, 1974.
mouse LD50 intravenous 14mg/kg (14mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 288, 1972.
mouse LD50 oral 228mg/kg (228mg/kg) BEHAVIORAL: ATAXIA Collection of Czechoslovak Chemical Communications. Vol. 42, Pg. 1179, 1977.
mouse LD50 subcutaneous > 16gm/kg (16000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 6, Pg. 629, 1972.
mouse LD50 subcutaneous > 16gm/kg (16000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS		 Kiso to Rinsho. Clinical Report. Vol. 6, Pg. 629, 1972.
rabbit LD50 intravenous 22mg/kg (22mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 5, Pg. 106, 1974.
rabbit LD50 oral 40mg/kg (40mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 5, Pg. 106, 1974.
rat LD50 intraperitoneal 350mg/kg (350mg/kg)   Drugs in Japan Vol. 6, Pg. 639, 1982.
rat LD50 intravenous 90mg/kg (90mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 5, Pg. 106, 1974.
rat LD50 oral 1100mg/kg (1100mg/kg)   Drugs in Japan Vol. 6, Pg. 639, 1982.
rat LD50 subcutaneous > 11gm/kg (11000mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE		 Kiso to Rinsho. Clinical Report. Vol. 6, Pg. 629, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 214-218 deg C   EXP
pKa Dissociation Constant 8.63 (none)   EXP
log P (octanol-water) 6.3 (none)   EXP
Water Solubility 10 mg/L 25 EXP
Vapor Pressure 6.25E-13 mm Hg 25 EST
Henry's Law Constant 1.10E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.46E-10 cm3/molecule-sec 25 EST

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