iloprost   

GtoPdb Ligand ID: 1895

Synonyms: Ventavis®
iloprost is an approved drug (EMA (2003), FDA (2004))
Compound class: Synthetic organic
Comment: Iloprost is a synthetic analogue of PGI2.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 77.76
Molecular weight 360.23
XLogP 3.19
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC#CCC(C(C=CC1C(O)CC2C1CC(=CCCCC(=O)O)C2)O)C
Isomeric SMILES CC#CCC([C@@H](/C=C/C1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)C
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
InChI Key HIFJCPQKFCZDDL-SGSAMSKHSA-N
No information available.
Summary of Clinical Use
Iloprost is used to treat pulmonary arterial hypertension, scleroderma, Raynaud's phenomenon and ischemia.
Mechanism Of Action and Pharmacodynamic Effects
Iloprost binds with equal affinity to human prostanoid (IP1) and prostaglandin EP1 receptors. Clinically iloprost acts as a vasodilator, hypotensive, antidiuretic, and anti-coagulant. These properties ameliorate disease-associated pathology observed in the small pulmonary arteries of patients with pulmonary hypertension.
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