propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate

• ChemBase编号: 172
• 分子式: C26H35F3O6
• 平均质量: 500.5477096
• 单一同位素质量: 500.2385735
• SMILES: FC(F)(F)c1cc(OC[C@H](O)/C=C/[C@@H]2[C@H]([C@@H](O)C[C@H]2O)C/C=C\CCCC(=O)OC(C)C)ccc1
• Canonical SMILES: CC(OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](COc1cccc(c1)C(F)(F)F)O)O)C
• InChI: InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1
• InChIKey: MKPLKVHSHYCHOC-AHTXBMBWSA-N

名称和登记号

名称

• IUPAC标准名: propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate
• IUPAC传统名: travoprost
• 商标名: Travatan; Travatan Z
• 别名: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; AL 6221; Travaprost; Travoprost; Travatan

登记号

• CAS号: 157283-68-6
• PubChem SID: 160963635; 46507637
• PubChem CID: 5282226

理论计算性质

JChem

• Acid pKa: 13.948069
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 3.839193
• LogD (pH = 7.4): 3.839193
• Log P: 3.839193
• 摩尔折射率: 127.8575 cm^3
• 极化性: 48.49126 Å^3
• 极化表面积: 96.22 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.02
• LOG S: -4.82
• 溶解度: 7.59e-03 g/l

分子性质

理化性质

• 溶解度: >16 mg/ml at 25.0°C; Acetonitrile; Chloroform; Dichloromethane; Methanol
• 外观: Colorless Oil
• 疏水性(logP): 4.6

安全信息

• 保存条件: -20°C; -20°C Freezer, Under Inert Atmosphere

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB00287

• Drug Groups: approved
• Description: Travoprost ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a synthetic prostaglandin F2alpha analogue. [Wikipedia]
• Indication: Ophthalmic solution used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication.
• Pharmacology: Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analogue that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid. The travoporst free acid is potent and highly selective for the FP prostanoid receptor.
• Toxicity: Symptoms of overexposure include irritation to the skin, eyes, nose, throat, and respiratory tract.
• Affected Organisms: Humans and other mammals
• Biotransformation: Travoprost, an isopropyl ester prodrug, is hydrolyzed by esterases in the cornea to its biologically active free acid. Systemically, travoprost free acid is metabolized to inactive metabolites via beta-oxidation of the α(carboxylic acid) chain to give the 1,2-dinor and 1,2,3,4-tetranor analogs, via oxidation of the 15-hydroxyl moiety, as well as via reduction of the 13,14 double bond.
• Absorption: Systemically absorbed when administered to the eye.
• Half Life: Terminal elimination half-life of travoprost free acid is 45 minutes.
• Elimination: Less than 2% of the topical ocular dose of travoprost was excreted in the urine within 4 hours as the travoprost free acid.
• References: Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. [Pubmed] ; Costagliola C, dell'Omo R, Romano MR, Rinaldi M, Zeppa L, Parmeggiani F: Pharmacotherapy of intraocular pressure - part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides. Expert Opin Pharmacother. 2009 Dec;10(17):2859-70. [Pubmed] ; Ferrari G, Scagliotti GV: Serum and urinary vascular endothelial growth factor levels in non-small cell lung cancer patients. Eur J Cancer. 1996 Dec;32A(13):2368-9. [Pubmed] ; Toris CB, Gabelt BT, Kaufman PL: Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction. Surv Ophthalmol. 2008 Nov;53 Suppl1:S107-20. [Pubmed] ; Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1554

Research Area: Cardiovascular Disease
Biological Activity:
Travoprost is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes. [1]

Toronto Research Chemicals - T715600

Selective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol. Antiglaucoma.

参考文献

• Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. Pubmed
• Costagliola C, dell'Omo R, Romano MR, Rinaldi M, Zeppa L, Parmeggiani F: Pharmacotherapy of intraocular pressure - part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides. Expert Opin Pharmacother. 2009 Dec;10(17):2859-70. Pubmed
• Ferrari G, Scagliotti GV: Serum and urinary vascular endothelial growth factor levels in non-small cell lung cancer patients. Eur J Cancer. 1996 Dec;32A(13):2368-9. Pubmed
• Toris CB, Gabelt BT, Kaufman PL: Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction. Surv Ophthalmol. 2008 Nov;53 Suppl1:S107-20. Pubmed
• Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. Pubmed
• http://en.wikipedia.org/wiki/Travoprost
• Hellberg, M.R., et al.: J. Ocul. Pharmacol. Ther., 17, 421 (2001)
• McCue, B.A., et al.: J. Pharm. Biomed. Anal., 28, 199 (2001)
• Schuman, J.S., et al.: Am. J. Ophthalmol., 140, 242 (2001)
• Carvalho, A.B., et al.: Vet. Ophthalmol., 9, 121 (2001)