(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide

• ChemBase编号: 126156
• 分子式: C25H37NO4
• 平均质量: 415.56558
• 单一同位素质量: 415.27225867
• SMILES: O=C(NCC)CCC/C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1C=C[C@@H](O)CCc1ccccc1
• Canonical SMILES: CCNC(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1C=C[C@H](CCc1ccccc1)O)O
• InChI: InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/t20-,21+,22+,23-,24+/m0/s1
• InChIKey: AQOKCDNYWBIDND-UDIRQSBCSA-N

名称和登记号

名称

• IUPAC标准名: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
• IUPAC传统名: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
• 商标名: Lumigan
• 别名: Bimatoprost; 17-Phenyl-tri-norprostaglandin F2α-ethyl amide; (5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide; 5-trans-Bimatoprost; (5E)-Bimatoprost; Bimatoprost

登记号

• CAS号: 155206-00-1; 1163135-95-2
• MDL号: MFCD03411999
• PubChem SID: 162220497
• PubChem CID: 5311027; 66509082
• CHEBI ID: 51230
• ATC码: S01EE03
• CHEMBL: 1200963
• Chemspider ID: 4470565
• DailyMed ID: 46098
• DrugBank ID: DB00905
• IUPHAR配体索引: 1958
• 美国药典/FDA物质标识码: QXS94885MZ
• 维基百科标题: Bimatoprost
• Medline Plus: a602030

理论计算性质

• Acid pKa: 14.34702
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): 2.6292617
• LogD (pH = 7.4): 2.6292624
• Log P: 2.6292624
• 摩尔折射率: 122.8312 cm^3
• 极化性: 47.097137 Å^3
• 极化表面积: 89.79 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: solid

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 给药途径: Topical (eye drops)
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: C (US)

产品相关信息

• 纯度: ≥95%
• Empirical Formula (Hill Notation): C25H37NO4

详细说明

Sigma Aldrich - P6740

Application
Potent FP prostanoid receptor agonist used in animal models for glaucoma.

Toronto Research Chemicals - B386810

The trans-isomer used in the improved process for the production and purification of Bimatoprost (B386800).