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Substance Name: Iloprost [USAN:INN:BAN]
RN: 78919-13-8
UNII: JED5K35YGL
InChIKey: HIFJCPQKFCZDDL-ACWOEMLNSA-N

Note

  • An eicosanoid, derived from the cyclooxygenase pathway of arachidonic acid metabolism. It is a stable and synthetic analog of EPOPROSTENOL, but with a longer half-life than the parent compound. Its actions are similar to prostacyclin. Iloprost produces vasodilation and inhibits platelet aggregation.

Molecular Formula

  • C22-H32-O4

Molecular Weight

  • 360.4908
 

Classification Codes

  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Hematologic Agents
  • Platelet Aggregation Inhibitors
  • Reproductive Effect
  • Treatment of Pulmonary Hypertension (Prostacyclin Analogue)
  • Vasodilator Agents

Names and Synonyms

Name of Substance

  • Iloprost
  • Iloprost [USAN:INN:BAN]

MeSH Heading

  • Iloprost

Synonyms

  • (16R,S)-Methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I(sub 2)
  • (E)-(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-((E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl)-delta(sup 2(1H),delta)-pentalenevaleric acid
  • (E)-5-(3aS,4R,5R,6aS)-5-Hydroxy-4((E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-inyl)perhydropentalen-2-yliden)valeriansaeure
  • BAY Q6256
  • Ciloprost
  • Iloprost
  • Iloprostum
  • Iloprostum [Latin]
  • UNII-JED5K35YGL
  • Ventavis
  • ZK 00036374
  • ZK 36374

Systematic Names

  • (E)-(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-((E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl)-delta(sup 2(1H),delta)-pentalenevaleric acid
  • Pentanoic acid, 5-(hexahydro-5-hydroxy-4-(3-hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)-pentalenylidene)-

Registry Numbers

CAS Registry Number

  • 78919-13-8

FDA UNII

  • JED5K35YGL

Other Registry Number

  • 73873-87-7

System Generated Number

  • 0078919138

Structure Descriptors

InChI

1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1

InChIKey

HIFJCPQKFCZDDL-ACWOEMLNSA-N

Smiles

CC#CCC(C)[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2C\C(=C/CCCC(=O)O)\C[C@H]12

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 201mg/kg (201mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
New Cardiovascular Drugs. Vol. 4, Pg. 209, 1986.
mouse LD50 oral > 100mg/kg (100mg/kg)   Drugs of the Future. Vol. 6, Pg. 676, 1981.
rat LD50 intravenous 119mg/kg (119mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
New Cardiovascular Drugs. Vol. 4, Pg. 209, 1986.
rat LD50 oral > 100mg/kg (100mg/kg)   Drugs of the Future. Vol. 6, Pg. 676, 1981.