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| | Travoprost Basic information |
| Product Name: | Travoprost | | Synonyms: | (+)-9ALPHA,11ALPHA,15R-TRIHYDROXY-16-(3-(TRIFLUOROMETHYL)PHENOXY)-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER;(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-methyethyl ester;(+/-)-16-(M-TRIFLUOROMETHYLPHENOXY)TETRANORPROSTAGLANDIN F2;15(S)-FLU-IPR;15(S)-FLUPROSTENOL ISOPROPYL ESTER;5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-, 1-methylethyl ester, (5Z)-;9ALPHA,11ALPHA,15S-TRIHYDROXY-16(3-(TRIFLUOROMETHYL)PHENOXY)-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER;(+)-FLUPROSTENOL ISOPROPYL ESTER | | CAS: | 157283-68-6 | | MF: | C26H35F3O6 | | MW: | 500.55 | | EINECS: | 682-028-9 | | Product Categories: | Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Prostaglandins | | Mol File: | 157283-68-6.mol |  |
| | Travoprost Chemical Properties |
| alpha | D20 +14.6° (c = 1.0 in methylene chloride) | | Boiling point | 584.8±50.0 °C(Predicted) | | density | 1.245±0.06 g/cm3(Predicted) | | Fp | 17 °C | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | Dichloromethane (Sparingly, Sonicated), Chloroform (Sparingy), Methanol (Sparing | | form | ethanol solution | | pka | 13.43±0.20(Predicted) | | color | Colourless to Light Beige | | BCS Class | 2 | | Stability: | Light Sensitive | | InChIKey | MKPLKVHSHYCHOC-AHTXBMBWSA-N | | CAS DataBase Reference | 157283-68-6(CAS DataBase Reference) |
| | Travoprost Usage And Synthesis |
| Description | Travoprost was launched in the US as Travatan?, an ophthalmic solution (0.004%)
administered topically for the treatment of elevated intraocular hypertension (lOP) through
open-angle glaucoma, a common optic neuropathy and a leading cause of blindness.
Travoprost is the isopropyl ester of (+)-fluprostenol, a new prostaglandin derivative
belonging to the PGF2α, analog class. This compound can be prepared in 8 steps from a
bicyclic lactone aldehyde by a Wittig alkylidenation followed, after 2 ketonic reductions, by
a lactol opening to prostenoic acid while protecting and deprotecting appropriately.
Travoprost is a full agonist of FP receptors with a greater affinity than PGF2α, (K1 = 52 nM).
Pharmacologic studies in rabbits treated daily for a week demonstrated a significant
increase of the microvascular optic nerve head blood flow without significant alterations in
the systemic flow. In several placebo-controlled clinical studies with hundreds of patients
suffering from open-angle glaucoma or ocular hypertension, travoprost (1 to 4 pm daily)
dose-dependently reduced lOP (by about 30% at 4 pm); it was shown equal or superior to
latanoprost, another prostaglandin analog (5 pm daily) or the adrenergic ~-blocker timolol
(500 pm bid). In addition, travoprost was safe and well tolerated with a low incidence of
conjunctival hyperaemia. | | Chemical Properties | Colorless Oil | | Originator | Alcon (US) | | Uses | Travoprost is a selective FP prostaglandin receptor agonist used to treat glaucoma (1,2). | | Uses | treatment conditions arising from excess uric acid, eg chronic gout | | Uses | Selective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol. Antiglaucoma | | Definition | ChEBI: The isopropyl ester of prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophth
lmic solutions of travoprost are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. It is a pro-drug; the isopropyl ester group is hydrolysed by esterases in the co
nea to the biologically active free acid, fluprostenol. | | Brand name | Travatan | | General Description | Travoprost (Travatan and Travatan-Z) is supplied asa 2.5- or 5.0-mL sterile 0.004% ophthalmic solution in a4.0- or 7.5-mL size container. Travoprost is claimed to bethe most potent and FP-specific analog in this product category. Cautions and side effects are similar to those givenpreviously. |
| | Travoprost Preparation Products And Raw materials |
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