Structure via PubChem · Public domain (PubChem)
prostacyclin
Sign in to saveAlso known as epoprostenol, prostaglandin I2, PGI2, (5Z,9alpha,11alpha,13e,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid, Epoprostenol, (5Z,13e)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate, Prostaglandin x
Prostacyclin (also called prostaglandin I2 or PGI2) is a prostaglandin member of the eicosanoid family of lipid molecules. It inhibits platelet activation and is also an effective vasodilator.
Chemical data
- Formula
- C20H32O5
- Molecular weight
- 352.5 g/mol
- IUPAC name
- (5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid
- SMILES
- CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O)O
- InChIKey
- KAQKFAOMNZTLHT-OZUDYXHBSA-N
- XLogP
- 2.9
- Polar surface area
- 87 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1995
- Admin. routes
- parenteral
- Indications
- Recurrent thrombophlebitis, subarachnoid hemorrhage, pulmonary arterial hypertension, ischemia reperfusion injury
via ChEMBL · EBI
Research
21,008 papers- Prostacyclin for pulmonary arterial hypertension.The Cochrane database of systematic reviews · 2019
- Targeting prostacyclin: all gain with no pain?Blood · 2023
- Prostacyclin Mitigates Renal Fibrosis by Activating Fibroblast Prostaglandin I 2 Receptor.Journal of the American Society of Nephrology : JASN · 2024
- Prostacyclin in Moscow.Cardiovascular research · 2024
- Muscle Injuries Induce a Prostacyclin-PPARγ/PGC1a-FAO Spike That Boosts Regeneration.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 352.224974
Show 8 more facts
- chemical formula
- C₂₀H₃₂O₅
- canonical SMILES
- CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)O)O2)O)O
- isomeric SMILES
- CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2O\C(C[C@H]12)=C/CCCC(O)=O
- NCI Thesaurus ID
- C61748
- subject has role
- primary metabolite
- found in taxon
- Homo sapiens
- Commons category
- Prostacyclin
- significant drug interaction
- apixaban
Sources (6)
via Wikidata · CC0
~9 min read
Encyclopedic overview
12 sectionsContents
- Function
- Medical uses
- Degradation
- Mechanism
- Members
- Pharmacology
- Synthesis
- Biosynthesis
- Artificial synthesis
- History
- References
- External links
Prostacyclin (also called prostaglandin I2 or PGI2) is a prostaglandin member of the eicosanoid family of lipid molecules. It inhibits platelet activation and is also an effective vasodilator.
When used as a drug, it is also known as epoprostenol. The terms are sometimes used interchangeably.
Excerpted from Wikipedia’s “prostacyclin” article, available under the CC BY-SA 4.0 licence.