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Substance Name: Alprostadil [USAN:USP:INN:BAN:JAN]
RN: 745-65-3
UNII: F5TD010360
InChIKey: GMVPRGQOIOIIMI-DWKJAMRDSA-N

Note

  • A potent vasodilator agent that increases peripheral blood flow.

Molecular Formula

  • C20-H34-O5

Molecular Weight

  • 354.4836
 

Classification Codes

  • Cardiovascular Agents
  • Fibrin Modulating Agents
  • Fibrinolytic Agents
  • Hematologic Agents
  • Hormone
  • Human Data
  • Mutation Data
  • Platelet Aggregation Inhibitors
  • Reproductive Effect
  • Urological Agents
  • Vasodilator
  • Vasodilator Agents

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Alprostadil

Synonyms

  • (-)-Protaglandin E1
  • (1R,2R,3R)-3-Hydroxy-2-((E)-(3S)-3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid
  • 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid
  • 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid
  • AI3-62116
  • Alprostadil
  • Alprostadilum
  • Alprostadilum [INN-Latin]
  • Alprox-TD
  • Caverject
  • Caverject Impulse
  • Edex
  • EINECS 212-017-2
  • Femprox
  • l-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid
  • l-PGE1
  • l-Prostaglandin E1
  • Lipoprost
  • Liprostin
  • Minprog
  • Muse
  • NSC 165559
  • ONO 1608
  • PGE-1
  • Promostan
  • Prostaglandin E1
  • Prostandin
  • Prostin
  • Prostin VR
  • Prostin VR Pediatric
  • Prostivas
  • Topiglan
  • U 10136
  • U-10,136
  • UNII-F5TD010360
  • Vasaprostan
  • Vitaros

Systematic Names

  • Alprostadil
  • Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)-
  • Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, l-
  • Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11alpha,13E,15S)-

Registry Numbers

CAS Registry Number

  • 745-65-3

FDA UNII

  • F5TD010360

Other Registry Numbers

  • 22299-37-2
  • 50-83-9
  • 50865-30-0

System Generated Number

  • 0000745653

Structure Descriptors

InChI

1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

InChIKey

GMVPRGQOIOIIMI-DWKJAMRDSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 19800ug/kg (19.8mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
mouse LD50 intravenous 21mg/kg (21mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
mouse LD50 oral 186mg/kg (186mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
mouse LD50 subcutaneous 26400ug/kg (26.4mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 intraarterial 21mg/kg (21mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 499, 1983.
rat LD50 intraperitoneal 24900ug/kg (24.9mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 intravenous 19200ug/kg (19.2mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 oral 228mg/kg (228mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.
rat LD50 subcutaneous 18600ug/kg (18.6mg/kg)   Drugs in Japan Vol. 6, Pg. 47, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 4.85 (none) 25 EXP
log P (octanol-water) 3.2 (none)   EXP
Water Solubility 26.7 mg/L 25 EST
Vapor Pressure 2.29E-13 mm Hg 25 EST
Henry's Law Constant 1.78E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.11E-10 cm3/molecule-sec 25 EST

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