ChemicalBook--->CAS DataBase List--->157283-68-6

157283-68-6

157283-68-6 Structure

157283-68-6 Structure
IdentificationMore
[Name]

Travoprost
[CAS]

157283-68-6
[Synonyms]

15(S)-FLU-IPR
15(S)-FLUPROSTENOL ISOPROPYL ESTER
(+/-)-16-(M-TRIFLUOROMETHYLPHENOXY)TETRANORPROSTAGLANDIN F2
(+)-9ALPHA,11ALPHA,15R-TRIHYDROXY-16-(3-(TRIFLUOROMETHYL)PHENOXY)-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER
9ALPHA,11ALPHA,15S-TRIHYDROXY-16(3-(TRIFLUOROMETHYL)PHENOXY)-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, ISOPROPYL ESTER
FLU-IPR
(+)-FLUPROSTENOL ISOPROPYL ESTER
FLUPROSTENOL ISOPROPYL ESTER
propan-2-yl (e)-7-[(1r,2s,3r,5s)-3,5-dihydroxy-2-[(e)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
TRAVOPROST
propan-2-yl 7-[(1R,2S,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
Propan-2-yl (E)-7-[(1R,2S,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
(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-Methylethyl Ester
AL 6221
Travaprost
Travatan
Travoprost, (±)-16-(m-Trifluoromethylphenoxy)tetranorprostaglandin F2
[EINECS(EC#)]

682-028-9
[Molecular Formula]

C26H35F3O6
[MDL Number]

MFCD03411995
[Molecular Weight]

500.55
[MOL File]

157283-68-6.mol
Chemical PropertiesBack Directory
[Appearance]

Colorless Oil
[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. ]

−20°C
[solubility ]

Dichloromethane (Sparingly, Sonicated), Chloroform (Sparingy), Methanol (Sparing
[form ]

ethanol solution
[pka]

13.43±0.20(Predicted)
[color ]

Colourless to Light Beige
[Usage]

Selective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol. Antiglaucoma
[BCS Class]

2
[Stability:]

Light Sensitive
[InChIKey]

MKPLKVHSHYCHOC-AHTXBMBWSA-N
[CAS DataBase Reference]

157283-68-6(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

F,Xi
[Risk Statements ]

R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

UN 1170 3/PG 2
[WGK Germany ]

1
[HS Code ]

2937500000
Hazard InformationBack Directory
[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)
[Uses]

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

treatment conditions arising from excess uric acid, eg chronic gout
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

Travoprost(157283-68-6)1HNMR
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