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Product Details:

  • Product Name: Travoprost
  • CAS #: 157283-68-6
  • Mode of Action:

    Travoprost free acid is a selective FP prostanoid receptor agonist and is believed to reduce intraocular pressure by increasing the drainage of aqueous humor, which is done primarily through increased uveoscleral outflow and to a lesser extent, trabecular outflow facility.

  • Pharmacodynamics:

    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.

  • Metabolism:

    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 _(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.

  • Toxicity:

    Symptoms of overexposure include irritation to the skin, eyes, nose, throat, and respiratory tract.

  • IUPAC: 5-Heptenoic acid, 7-((1R, 2R, 3R, 5S)-3, 5-dihydroxy-2-((1E, 3R)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl ester, (5Z)-
  • ATC: S01EE04
  • PubChem: 656627
  • DrugBank: DB00287 (APRD01271)
  • Formula: C26-H35-F3-O6
  • Molecular Mass: 500.551
  • Synonyms: (((1R)-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic acid, 1-methylethyl ester, (1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-7-(3,5-Dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic acid, 1-methylethyl ester, (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3R)-3-hydroxy-4-((alpha,alpha,alpha-trifluoro-m-isopropyl-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate, 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl ester, (1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-, AL-6221, AL6221, Izba, Travatan, Travatan Z, Travoprost, UNII-WJ68R08KX9
  • SMILES: C1[C@H]([C@@H]([C@H]([C@H]1O)CC=CCCCC(OC(C)C)=O)C=C[C@@H](COc1cc(ccc1)C(F)(F)F)O)O
  • AHFS Code: 53:32.0
  • InChl: 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
  • General Reference:

     

    1. Lim KS, Nau CB, OêByrne 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
    2. Costagliola C, dellêOmo 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
    3. 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
    4. 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
    5. Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. Pubmed

     

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