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CHEBI:63916 - iloprost

ChEBI IDCHEBI:63916
ChEBI Nameiloprost
Stars
DefinitionA carbobicyclic compound that is prostaglandin I2 in which the endocyclic oxygen is replaced by a methylene group and in which the (1E,3S)-3-hydroxyoct-1-en-1-yl side chain is replaced by a (3R)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl group. A synthetic analogue of prostacyclin, it is used as the trometamol salt (generally by intravenous infusion) for the treatment of peripheral vascular disease and pulmonary hypertension.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H32O4
Net Charge0
Average Mass360.494
Monoisotopic Mass360.23006
SMILES[H][C@]1(/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]2C/C(=C\CCCC(=O)O)C[C@@H]21
InChIInChI=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
InChIKeyHIFJCPQKFCZDDL-ACWOEMLNSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Applications:
platelet aggregation inhibitor  A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
vasodilator agent  A drug used to cause dilation of the blood vessels.
ChEBI Ontology
Outgoing Relation(s)
iloprost (CHEBI:63916) has role platelet aggregation inhibitor (CHEBI:50427)
iloprost (CHEBI:63916) has role vasodilator agent (CHEBI:35620)
iloprost (CHEBI:63916) is a carbobicyclic compound (CHEBI:36785)
iloprost (CHEBI:63916) is a monocarboxylic acid (CHEBI:25384)
iloprost (CHEBI:63916) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]hexahydropentalen-2(1H)-ylidene]pentanoic acid
INNs  Source
iloprostumChemIDplus
iloprostChemIDplus
Synonym  Source
(16R,S)-methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I2ChemIDplus
Manual XrefsDatabases
DE2845770Patent
US4692464Patent
D02721KEGG DRUG
DB01088DrugBank
IloprostWikipedia
1422DrugCentral
Registry NumbersSources
Reaxys:4329060Reaxys
CAS:78919-13-8KEGG DRUG
Citations