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. 

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)

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

• Language:English Provider:SigmaAldrich

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 PGF_2α, 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_2α, (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(157283-68-6)Related Product Information

• Anisole
• Glycolic acid
• CHLOROPHOSPHONAZO III
• (Trifluoromethoxy)benzene
• Methylparaben
• Prostaglandin E2
• Hydroxy silicone oil
• Epoprostenol
• Propane
• HYDROXYAPATITE TYPE I
• 4-Hydroxybenzaldehyde
• Prostaglandin E1
• Bimatoprost
• Latanoprost
• (+)-Fluprostenol
• 9-KETO FLUPROSTENOL
• 9-keto Fluprostenol isopropyl ester
• 15-Keto Travoprost