Iloprost
(5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
Molecular Identity
Iloprost
(5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
PubChem CID: 5311181
Iloprost is 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. It has a role as a vasodilator agent and a platelet aggregation inhibitor. It is a monocarboxylic acid, a secondary alcohol and a carbobicyclic compound.
2D Structure
Properties
C22H32O4
Molecular Formula
360.50
Molecular Weight
g/mol
360.2301
Exact Mass
Da
2.8
XLogP
Drug-like (Lipinski: < 5)
77.8
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
4
H-Bond Acceptors
606
Complexity
SMILES
Canonical SMILES
SMILES: CC#CCC(C)C(C=CC1C(CC2C1CC(=CCCCC(=O)O)C2)O)OIsomeric SMILES
SMILES: CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)OSynonyms(20)
ILOPROST78919-13-8CiloprostVentavisEndoprostIlomedinAurlumynIloprostumZK-36374DTXSID2041046JED5K35YGLZK 36374ZK 00036374CHEBI:63916ZK-00036374
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Iloprost
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