5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

• ChemBase ID: 1109
• Molecular Formular: C20H32O5
• Molecular Mass: 352.46508
• Monoisotopic Mass: 352.22497412
• SMILES: O1[C@@H]2[C@@H]([C@H]([C@H](O)C2)/C=C/[C@@H](O)CCCCC)CC1=CCCCC(=O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1CC(=CCCCC(=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
• InChIKey: KAQKFAOMNZTLHT-VVUHWYTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid; 5-[(2Z,3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid
• IUPAC Traditional name: 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; epoprostenol
• Brand Name: Flolan
• Synonyms: PGI2; Prostacyclin; Prostaglandin I2; Epoprostenol; Prostacyclin

Database IDs

• CAS Number: 35121-78-9
• PubChem SID: 46507362; 160964572
• PubChem CID: 5280427; 114805; 5282411
• ATC CODE: B01AC09
• CHEMBL: 962
• DrugBank ID: DB01240
• Wikipedia Title: Prostacyclin

CALCULATED PROPERTIES

JChem

• LogD (pH = 5.5): 1.3110825
• LogD (pH = 7.4): -0.44954696
• Log P: 2.4157045
• Molar Refractivity: 99.0069 cm^3
• Polarizability: 38.081345 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true
• Acid pKa: 4.4292903
• H Acceptors: 5
• H Donor: 3

ALOGPS 2.1

• Log P: 3.83
• LOG S: -3.41
• Solubility (Water): 1.36e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3

DETAILS

DrugBank - DB01240

• Drug Groups: approved
• Description: A prostaglandin that is a powerful vasodilator and inhibits platelet aggregation. It is biosynthesized enzymatically from prostaglandin endoperoxides in human vascular tissue. The sodium salt has been also used to treat primary pulmonary hypertension.
• Indication: For the long-term intravenous treatment of primary pulmonary hypertension and pulmonary hypertension associated with the scleroderma spectrum of disease in NYHA Class III and Class IV patients who do not respond adequately to conventional therapy.
• Pharmacology: Epoprostenol has two major pharmacological actions: (1) direct vasodilation of pulmonary and systemic arterial vascular beds, and (2) inhibition of platelet aggregation. In animals, the vasodilatory effects reduce right and left ventricular afterload and increase cardiac output and stroke volume. The effect of epoprostenol on heart rate in animals varies with dose. At low doses, there is vagally mediated brudycardia, but at higher doses, epoprostenol causes reflex tachycardia in response to direct vasodilation and hypotension. No major effects on cardiac conduction have been observed. Additional pharmacologic effects of epoprostenol in animals include bronchodilation, inhibition of gastric acid secretion, and decreased gastric emptying. No available chemical assay is sufficiently sensitive and specific to assess the in vivo human pharmacokinetics of epoprostenol.
• Toxicity: Symptoms of overdose are extensions of its dose-limiting pharmacologic effects and include flushing, headache, hypotension, nausea, vomiting, and diarrhea. Most events were self-limiting and resolved with reduction or withholding of epoprostenol. Single intravenous doses at 10 and 50 mg/kg (2703 and 27,027 times the recommended acute phase human dose based on body surface area) were lethal to mice and rats, respectively. Symptoms of acute toxicity were hypoactivity, ataxia, loss of righting reflex, deep slow breathing, and hypothermia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Epoprostenol is metabolized to 2 primary metabolites: 6-keto-PGF1α (formed by spontaneous degradation) and 6,15-diketo-13,14-dihydro-PGF1α (enzymatically formed), both of which have pharmacological activity orders of magnitude less than epoprostenol in animal test systems. Fourteen additional minor metabolites have been isolated from urine, indicating that epoprostenol is extensively metabolized in humans.
• Half Life: The in vitro half-life of epoprostenol in human blood at 37°C and pH 7.4 is approximately 6 minutes; the in vivo half-life of epoprostenol in humans is therefore expected to be no greater than 6 minutes.
• Elimination: Epoprostenol is metabolized to 2 primary metabolites: 6-keto-PGF1α (formed by spontaneous degradation) and 6,15-diketo-13,14-dihydro-PGF1α (enzymatically formed), both of which have pharmacological activity orders of magnitude less than epoprostenol in animal test systems. Fourteen additional minor metabolites have been isolated from urine, indicating that epoprostenol is extensively metabolized in humans.
• Distribution: * 357 mL/kg
• External Links: Wikipedia; RxList; Drugs.com