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HomeProduct name listTravoprost

Travoprost

Synonym(s):(±)-16-(m-Trifluoromethylphenoxy)tetranorprostaglandin F2;Travoprost;Travoprost solution

  • CAS NO.:157283-68-6
  • Empirical Formula: C26H35F3O6
  • Molecular Weight: 500.55
  • MDL number: MFCD03411995
  • EINECS: 682-028-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Travoprost Structural

What is Travoprost?

Absorption

Travoprost is systemically absorbed through the cornea . In humans, peak plasma concentrations of travoprost free acid were low (25 pg/mL or less) and occurred within 30 minutes following topical ocular administration of one drop of 0.004% travoprost ophthalmic solution .

Toxicity

No cases of overdose have been reported for travoprost . A topical overdose is not likely to occur or to be associated with toxicity . A topical overdose of travoprost may be flushed from the eye(s) with lukewarm water . Treatment of a suspected oral ingestion is symptomatic and supportive .
Travoprost has harmful pharmacological effects on pregnancy and/or the fetus/new-born child. Travoprost should not be used during pregnancy unless clearly necessary . The medication subsequently must not be used in women of childbearing age/potential unless adequate contraceptive measures are in place .
It is unknown whether travoprost from the eye drops is excreted in human breast milk. Animal studies have shown excretion of travoprost and metabolites in breast milk . The use of travoprost by breast-feeding mothers is not recommended .
There are no data on the effects of TRAVATAN on human fertility . Animal studies showed no effect of travoprost on fertility at doses more than 250 times the maximum recommended human ocular dose .
Use in patients below the age of 16 years is not recommended because of potential safety concerns related to increased pigmentation following long-term chronic use .
No overall clinical differences in safety or effectiveness have been observed between elderly and other adult patients .
Travoprost has been studied in patients with mild to severe hepatic impairment and in patients with mild to severe renal impairment (creatinine clearance as low as 14 ml/min) . No dosage adjustment is necessary for these patients .

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, 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 properties

Colorless Oil

Originator

Alcon (US)

The Uses of Travoprost

Travoprost is a selective FP prostaglandin receptor agonist used to treat glaucoma (1,2).

The Uses of Travoprost

Selective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol. Antiglaucoma

The Uses of Travoprost

treatment conditions arising from excess uric acid, eg chronic gout

Background

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 analog . Having been a well-received therapeutic agent with demonstrated efficacy and safety, travoprost is currently approved by the US FDA as a first-line treatment for lowering intraocular pressure in patients with open-angle glaucoma or ocular hypotension . Furthermore, this approval also solidifies the medication as the first and only prostaglandin analog approved by the FDA for first-line treatment of glaucoma patients that does not contain the preservative benzalkonium chloride . Moreover, travoprost is also currently approved in the EU for the decrease of elevated intraocular pressure in paediatric patients aged 2 months to < 18 years with ocular hypertension or paediatric glaucoma .

What are the applications of Application

Fluprostenol isopropyl ester is a prodrug PGF2αR agonist

Indications

Travoprost ophthalmic solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension .
Travoprost is also currently indicated for the decrease of elevated intraocular pressure in paediatric patients aged 2 months to < 18 years with ocular hypertension or paediatric glaucoma .

What are the applications of Application

15(S)-Fluprostenol isopropyl ester is an unnatural C-15 epimer of Travoprost

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.

Pharmacokinetics

Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analog that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid . The travoprost 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 rapidly and extensively metabolized in the kidney, liver, and lung 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 .

Properties of Travoprost

Boiling point: 584.8±50.0 °C(Predicted)
alpha  D20 +14.6° (c = 1.0 in methylene chloride)
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
pka 13.43±0.20(Predicted)
form  ethanol solution
color  Colourless to Light Beige
Stability: Light Sensitive
CAS DataBase Reference 157283-68-6(CAS DataBase Reference)

Safety information for Travoprost

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P240:Ground/bond container and receiving equipment.
P241:Use explosion-proof electrical/ventilating/lighting/…/equipment.
P242:Use only non-sparking tools.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Travoprost

InChIKey MKPLKVHSHYCHOC-AHTXBMBWSA-N

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