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编号: 959
• 分子式: C30H38O5
• 平均质量: 478.61972
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: ciloprost
• 商标名: Ventavis
• 别名: iloprost; Iloprost

登记号

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

理论计算性质

JChem

• Acid pKa: 13.723218
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.942495
• LogD (pH = 7.4): 4.942495
• Log P: 4.942495
• 摩尔折射率: 139.853 cm^3
• 极化性: 53.542786 Å^3
• 极化表面积: 83.83 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 5.04
• LOG S: -5.38
• 溶解度: 2.00e-03 g/l

分子性质

理化性质

• 溶解度: Very slightly soluble
• 疏水性(logP): 4.8

详细说明

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