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Substance Name: Gemeprost [USAN:INN:BAN:JAN]
RN: 64318-79-2
UNII: 45KZB1FOLS
InChIKey: KYBOHGVERHWSSV-VNIVIJDLSA-N

Note

  • Used for preoperative dilation of cervix before surgical abortion.

Molecular Formula

  • C23-H38-O5

Molecular Weight

  • 394.5482
 

Classification Codes

  • Abortifacient Agents
  • Abortifacient Agents, Nonsteroidal
  • Human Data
  • Prostaglandin
  • Reproductive Control Agents
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Gemeprost
  • Gemeprost [USAN:INN:BAN:JAN]

Synonyms

  • 16,16-Dimethyl-trans-delta(sup 2)-prostaglandin E1 methyl ester
  • 16,16-Dimethyl-trans-delta-2-PGE1 methyl ester
  • 16,16-Dimethyl-trans-delta-2-prostaglandin e1 methyl ester
  • Carprost
  • Cervagem
  • EINECS 264-775-9
  • Gemeprost
  • Gemeprostum
  • Gemeprostum [INN-Latin]
  • Methyl (E)-7-((1R,2R,3R)-3-hydroxy-2-((E)-(3R)-3-hydroxy-4,4-dimethyl-1-octenyl)-5-oxocyclopentyl)-2-heptenoate
  • Methyl 16,16-dimethyl-trans-delta-2-PGE1
  • ONO 802
  • Preglandin
  • SC 37681
  • SC-37681
  • trans-2,3-Didehydro-16,16-dimethyl PGE1 methyl ester
  • UNII-45KZB1FOLS

Systematic Names

  • (2E,11alpha,13E,15R)-11,15-Dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oic acid, methyl ester
  • Gemeprost
  • Prosta-2,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, methyl ester, (2E,11alpha,13E,15R)-

Registry Numbers

CAS Registry Number

  • 64318-79-2

FDA UNII

  • 45KZB1FOLS

Other Registry Number

  • 65135-28-6

System Generated Number

  • 0064318792

Structure Descriptors

InChI

1S/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13+/t17-,18-,20-,21-/m1/s1

InChIKey

KYBOHGVERHWSSV-VNIVIJDLSA-N

Smiles

CCCCC(C)(C)[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCC/C=C/C(=O)OC)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravaginal 36mg/kg (36mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
mouse LD50 intravenous 29500ug/kg (29.5mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
mouse LD50 oral 59mg/kg (59mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
mouse LD50 subcutaneous 32500ug/kg (32.5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
rat LD50 intravaginal 32500ug/kg (32.5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
rat LD50 intravenous 28600ug/kg (28.6mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
rat LD50 oral 56500ug/kg (56.5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.
rat LD50 subcutaneous 22600ug/kg (22.6mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Gendai Iryo. Modern Medical Care. Vol. 14, Pg. 188, 1982.