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Travoprost

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Travoprost Basic information
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)
  • Flash point:17 °C
  • storage temp. −20°C
  • pka13.43±0.20(Predicted)
  • form ethanol solution
  • InChIKeyMKPLKVHSHYCHOC-AHTXBMBWSA-N
  • CAS DataBase Reference157283-68-6(CAS DataBase Reference)
Safety Information
  • Hazard Codes F,Xi
  • Risk Statements 11-36/37/38
  • Safety Statements 16-26-36-7
  • RIDADR UN 1170 3/PG 2
  • WGK Germany 1
  • HS Code 2937500000
MSDS
Travoprost Usage And Synthesis
  • DescriptionTravoprost 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 PGF, 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 PGF, (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 PropertiesColorless Oil
  • OriginatorAlcon (US)
  • UsesSelective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol. Antiglaucoma
  • Usestreatment conditions arising from excess uric acid, eg chronic gout
  • DefinitionChEBI: 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 nameTravatan
  • General DescriptionTravoprost (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.
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