PGI2   Click here for help

GtoPdb Ligand ID: 1915

Synonyms: prostacyclin | prostacyclin I2 | prostaglandin I2 | vasocyclin
Approved drug
PGI2 is an approved drug (FDA (1995))
Comment: PGI2 is an endogenous prostaglandin. Synthetic PGI2 is known as epoprostenol. PG12 activates prostanoid family GPCRs.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 86.99
Molecular weight 352.22
XLogP 2.98
No. Lipinski's rules broken 0
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Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O
InChI InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
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Summary of Clinical Use Click here for help
Used in the long term treatment of primary pulmonary hypertension.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Activates the prostacylin receptor which causes the production of cAMP via adenylyl cyclase siganalling. cAMP then inhibits platelet activation. Binding of epoprostenol to prostacyclin receptors raises cAMP levels in the cytosol, which in turn activates protein kinase A. Protein kinase A phosphorylates and inhibits myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation.