CHEBI:63916 - iloprost

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ChEBI Name iloprost
ChEBI ID CHEBI:63916
Definition A 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.
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Formula C22H32O4
Net Charge 0
Average Mass 360.48710
Monoisotopic Mass 360.230
InChI 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 [H][C@]1(\C=C\[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]2C\C(C[C@H]12)=C/CCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
iloprost ChemIDplus
iloprostum ChemIDplus
Synonym Source
(16R,S)-methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I2 ChemIDplus
Database Links Databases
1422 DrugCentral
D02721 KEGG DRUG
DB01088 DrugBank
DE2845770 Patent
Iloprost Wikipedia
US4692464 Patent
View more database links
Registry Numbers Types Sources
4329060 Reaxys Registry Number Reaxys
78919-13-8 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
14719835 PubMed citation Europe PMC
15232651 PubMed citation Europe PMC
15241524 PubMed citation Europe PMC
19436672 PubMed citation Europe PMC
Last Modified
22 February 2017