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Substance Name: Dinoprostone [USAN:USP:INN:BAN:JAN]
RN: 363-24-6
UNII: K7Q1JQR04M
InChIKey: XEYBRNLFEZDVAW-ARSRFYASSA-N

Note

  • The most common and most biologically active of the mammalian prostaglandins. It exhibits most biological activities characteristic of prostaglandins and has been used extensively as an oxytocic agent. The compound also displays a protective effect on the intestinal mucosa.

Molecular Formula

  • C20-H32-O5

Molecular Weight

  • 352.468
 

Classification Codes

  • Drug / Therapeutic Agent
  • Hormone
  • Human Data
  • Mutation Data
  • Oxytocic
  • Oxytocics
  • Prostaglandin
  • Reproductive Control Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Dinoprostone

Synonyms

  • (15S)-Prostaglandin E2
  • (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid
  • 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-, l-
  • 7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
  • Cervidil
  • Cerviprime
  • Cerviprost
  • Dinoproston
  • Dinoprostona
  • Dinoprostona [INN-Spanish]
  • Dinoprostone
  • Dinoprostonum
  • Dinoprostonum [INN-Latin]
  • EINECS 206-656-6
  • Enzaprost E
  • Glandin
  • l-7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
  • l-PGE2
  • l-Prostaglandin E2
  • Minprositin E2
  • Minprostin E2
  • NSC 165560
  • NSC 196514
  • PGE2
  • Prepidil
  • Propess
  • Prostaglandin E2
  • Prostarmon E
  • Prostenone
  • Prostin
  • Prostin E2
  • U 12062
  • U-12,062
  • U-12062
  • UNII-K7Q1JQR04M

Systematic Names

  • 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)- (8CI)
  • Dinoprostone
  • Prosta-5,13-dien-1-oic acid, (5Z,11-alpha,13E,15S)-11,15-dihydroxy-9-oxo-
  • Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11alpha,13E,15S)-

Registry Numbers

CAS Registry Number

  • 363-24-6

FDA UNII

  • K7Q1JQR04M

System Generated Number

  • 0000363246

Structure Descriptors

InChI

1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

InChIKey

XEYBRNLFEZDVAW-ARSRFYASSA-N

Smiles

C1([C@@H]([C@H]([C@@H](C1)O)\C=C\[C@@H](O)CCCCC)C\C=C/CCCC(=O)O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 intraperitoneal 1mg/kg (1mg/kg)   Prostaglandins, Leukotrienes and Medicine. Vol. 17, Pg. 309, 1985.
mouse LD50 intravenous 23200ug/kg (23.2mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 787, 1974.
mouse LD50 oral 750mg/kg (750mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 787, 1974.
mouse LD50 subcutaneous 19700ug/kg (19.7mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 787, 1974.
rat LD50 intravenous 59500ug/kg (59.5mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 787, 1974.
rat LD50 oral 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 787, 1974.
rat LD50 subcutaneous 31600ug/kg (31.6mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 787, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 67 deg C   EXP
log P (octanol-water) 2.82 (none)   EXP
Water Solubility 58.1 mg/L 25 EST
Vapor Pressure 1.68E-13 mm Hg 25 EST
Henry's Law Constant 1.56E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.63E-10 cm3/molecule-sec 25 EST

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