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 ID: 172
• Molecular Formular: C26H35F3O6
• Molecular Mass: 500.5477096
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: travoprost
• Brand Name: Travatan; Travatan Z
• Synonyms: (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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.948069
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.839193
• LogD (pH = 7.4): 3.839193
• Log P: 3.839193
• Molar Refractivity: 127.8575 cm^3
• Polarizability: 48.49126 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.02
• LOG S: -4.82
• Solubility (Water): 7.59e-03 g/l

PROPERTIES

Physical Property

• Solubility: >16 mg/ml at 25.0°C; Acetonitrile; Chloroform; Dichloromethane; Methanol
• Apperance: Colorless Oil
• Hydrophobicity(logP): 4.6

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere

Product Information

• Salt Data: Free Base

DETAILS

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.

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
• 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)