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Substance Name: Metopimazine [USAN:INN:BAN]
RN: 14008-44-7
UNII: 238S75V9AV
InChIKey: BQDBKDMTIJBJLA-UHFFFAOYSA-N

Classification Codes

  • Anti-Emetic
  • Antiemetics
  • Autonomic Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Peripheral Nervous System Agents

Molecular Formula

  • C22-H27-N3-O3-S2

Molecular Weight

  • 445.6053
 
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Names and Synonyms

Name of Substance

  • Metopimazine
  • Metopimazine [USAN:INN:BAN]

Synonyms

  • 1-(3-(2-(Methylsulfonyl)-10H-phenothiazin-10-yl)propyl)-4-piperidinecarboxamide
  • 1-(3-(2-(Methylsulfonyl)phenothiazin-10-yl)propyl)-4-piperidinecarboxamide
  • 1-(3-(2-(Methylsulfonyl)phenothiazin-10-yl)propyl)isonipecotamide
  • 10-(3-(4-Carbamoylpiperidine)propyl)-2-(methanesulfonyl)phenothiazine
  • 2-Methylsulfonyl-10-(3-(4-carbamoylpiperidino)propyl)phenothiazine
  • 4-Piperidinecarboxamide, 1-(3-(2-(methanesulfonyl)phenothiazin-10-yl)propyl)-
  • 4-Piperidinecarboxamide, 1-(3-(2-(methylsulfonyl)-10H-phenothiazin-10-yl)propyl)-
  • BRN 4278585
  • EINECS 237-818-4
  • EXP 999
  • Metopimazina
  • Metopimazina [INN-Spanish]
  • Metopimazine
  • Metopimazinum
  • Metopimazinum [INN-Latin]
  • Nortrip
  • Phenothiazine, 10-(3-(4'-carbamoylpiperidino)propyl)-2-methylsulfonyl-
  • RP 9965
  • UNII-238S75V9AV
  • Vogalene

Systematic Names

  • 4-Piperidinecarboxamide, 1-(3-(2-(methylsulfonyl)-10H-phenothiazin-10-yl)propyl)-
  • Isonipecotamide, 1-(3-(2-(methylsulfonyl)phenothiazin-10-yl)propyl)-
  • Metopimazine

Registry Numbers

CAS Registry Number

  • 14008-44-7

FDA UNII

  • 238S75V9AV

Other Registry Number

  • 14170-03-7

System Generated Number

  • 0014008447

Structure Descriptors

InChI

1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)

InChIKey

BQDBKDMTIJBJLA-UHFFFAOYSA-N

Smiles

CS(=O)(=O)c1ccc2c(c1)N(c3ccccc3S2)CCCN4CCC(CC4)C(=O)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 500mg/kg (500mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
cat LDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
dog LD50 oral 500mg/kg (500mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
dog LD50 oral 500mg/kg (500mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
guinea pig LDLo oral 250mg/kg (250mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
guinea pig LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
mouse LD50 intraperitoneal 78mg/kg (78mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN SENSATION OF SMELL: OLFACTION
Oyo Yakuri. Pharmacometrics. Vol. 1, Pg. 97, 1967.
mouse LD50 intravenous 64mg/kg (64mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN SENSATION OF SMELL: OLFACTION
Oyo Yakuri. Pharmacometrics. Vol. 1, Pg. 97, 1967.
mouse LD50 oral 800mg/kg (800mg/kg)   Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles. Vol. 266, Pg. 2365, 1968.
mouse LD50 subcutaneous 315mg/kg (315mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 32, 1972.
rabbit LDLo oral 2gm/kg (2000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
rabbit LDLo oral 2gm/kg (2000mg/kg) BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
Oyo Yakuri. Pharmacometrics. Vol. 11, Pg. 561, 1976.
rat LD50 oral 976mg/kg (976mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous 1080mg/kg (1080mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 170.5 deg C   EXP
log P (octanol-water) 2.420 (none)   EST
Atmospheric OH Rate Constant 2.34E-10 cm3/molecule-sec 25 EST

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