2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate

• ChemBase ID: 959
• Molecular Formular: C30H38O5
• Molecular Mass: 478.61972
• Monoisotopic Mass: 478.27192432
• SMILES: OC1C(C2C(C1)C/C(=C/CCCC(=O)OCC(=O)c1ccccc1)/C2)/C=C/C(O)C(CC#CC)C
• Canonical SMILES: CC#CCC(C(/C=C/C1C(O)CC2C1C/C(=C\CCCC(=O)OCC(=O)c1ccccc1)/C2)O)C
• InChI: InChI=1S/C30H38O5/c1-3-4-10-21(2)27(31)16-15-25-26-18-22(17-24(26)19-28(25)32)11-8-9-14-30(34)35-20-29(33)23-12-6-5-7-13-23/h5-7,11-13,15-16,21,24-28,31-32H,8-10,14,17-20H2,1-2H3/b16-15+,22-11-
• InChIKey: CZUMMMDKQYRZDP-JCAXBLPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate
• IUPAC Traditional name: ciloprost
• Brand Name: Ventavis
• Synonyms: iloprost; Iloprost

Database IDs

• CAS Number: 78919-13-8
• PubChem SID: 46507818; 160964422
• PubChem CID: 6443959

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.723218
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.942495
• LogD (pH = 7.4): 4.942495
• Log P: 4.942495
• Molar Refractivity: 139.853 cm^3
• Polarizability: 53.542786 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.04
• LOG S: -5.38
• Solubility (Water): 2.00e-03 g/l

PROPERTIES

Physical Property

• Solubility: Very slightly soluble
• Hydrophobicity(logP): 4.8

DETAILS

DrugBank - DB01088

• Drug Groups: approved; investigational
• Description: Iloprost is a synthetic analogue of prostacyclin PGI2. Iloprost dilates systemic and pulmonary arterial vascular beds. It is used to treat pulmonary arterial hypertension (PAH).
• Indication: Used for the treatment of pulmonary arterial hypertension.
• Pharmacology: Iloprost is a synthetic analogue of prostacyclin PGI2. Iloprost dilates systemic and pulmonary arterial vascular beds. It also affects platelet aggregation but the relevance of this effect to the treatment of pulmonary hypertension is unknown. The two diastereoisomers of iloprost differ in their potency in dilating blood vessels, with the 4S isomer substantially more potent than the 4R isomer.
• Toxicity: Overdoses can lead to hypotension, headache, flushing, nausea, vomiting, and diarrhea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. Iloprost is metabolized principally via beta-oxidation of the carboxyl side chain.
• Absorption: Rapidly absorbed with bioavailability of 63%
• Half Life: 20-30 minutes
• Protein Binding: 60%
• Distribution: * 0.7 to 0.8 L/kg
• Clearance: * 20 mL/min/kg [Normal subjects]
• External Links: Wikipedia; RxList; Drugs.com