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Substance Name: Misoprostol [USAN:USP:INN:BAN:JAN]
RN: 59122-46-2
UNII: 0E43V0BB57
InChIKey: OJLOPKGSLYJEMD-URPKTTJQSA-N

Note

  • A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.

Molecular Formula

  • C22-H38-O5

Molecular Weight

  • 382.5372
 

Classification Codes

  • Abortifacient Agents
  • Abortifacient Agents, Nonsteroidal
  • Anti-Ulcer Agents
  • Anti-Ulcerative
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Oxytocics
  • Reproductive Control Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Misoprostol

Synonyms

  • (+-)-Methyl (1R,2R,3R)-3-hydroxy-2-((E)-(4RS)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate
  • (11-alpha,13E)-(+-)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester
  • BRN 4155643
  • CCRIS 6859
  • Cytotec
  • HSDB 3573
  • Isprelor
  • Methyl (+-)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate
  • Misogon
  • Misoprost
  • Misoprostil
  • Misoprostol
  • Misoprostolum
  • Misoprostolum [INN-Latin]
  • Misotac
  • Misotol
  • MVI 200
  • SC 29333
  • SC-29333
  • UNII-0E43V0BB57

Systematic Names

  • Misoprostol
  • Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11alpha,13E)-
  • Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11alpha,13E)-(+-)-

Superlist Name

  • Misoprostol

Mixture Name

  • Arthrotec

Registry Numbers

CAS Registry Number

  • 59122-46-2

FDA UNII

  • 0E43V0BB57

Other Registry Numbers

  • 138284-96-5
  • 143913-16-0
  • 62015-39-8
  • 92999-98-9

System Generated Number

  • 0059122462

Structure Descriptors

InChI

1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1

InChIKey

OJLOPKGSLYJEMD-URPKTTJQSA-N

Smiles

CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 10mg/kg (10mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 1055, 1993.
mouse LD50 intramuscular 16mg/kg (16mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 33, 1985.
mouse LD50 intraperitoneal 70mg/kg (70mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Digestive Diseases and Sciences. Vol. 30, Pg. 142S, 1985.
mouse LD50 oral 27mg/kg (27mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Digestive Diseases and Sciences. Vol. 30, Pg. 142S, 1985.
rat LD50 intramuscular 19mg/kg (19mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 33, 1985.
rat LD50 intraperitoneal 40mg/kg (40mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Digestive Diseases and Sciences. Vol. 30, Pg. 142S, 1985.
rat LD50 oral 81mg/kg (81mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 33, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 4.960 (none)   EST
Water Solubility 0.186 mg/L 25 EST
Henry's Law Constant 1.00E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.15E-10 cm3/molecule-sec 25 EST

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