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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: pgi2

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1995))
IUPAC Name Click here for help
(5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[d]furan-2-ylidene]pentanoic acid
International Nonproprietary Names Click here for help
INN number INN
4725 epoprostenol
Synonyms Click here for help
prostacyclin | prostacyclin I2 | prostaglandin I2 | vasocyclin
Database Links Click here for help
Specialist databases
GPCRdb Ligand PGI2
Other databases
CAS Registry No. 35121-78-9 (source: Scifinder)
ChEMBL Ligand CHEMBL1139
DrugBank Ligand DB01240
DrugCentral Ligand 1034
GtoPdb PubChem SID 135651541
PubChem CID 5282411
Search Google for chemical match using the InChIKey KAQKFAOMNZTLHT-OZUDYXHBSA-N
Search Google for chemicals with the same backbone KAQKFAOMNZTLHT
Search PubMed clinical trials epoprostenol
Search PubMed titles epoprostenol
Search PubMed titles/abstracts epoprostenol
UniChem Compound Search for chemical match using the InChIKey KAQKFAOMNZTLHT-OZUDYXHBSA-N
UniChem Connectivity Search for chemical match using the InChIKey KAQKFAOMNZTLHT-OZUDYXHBSA-N
Wikipedia Prostacyclin