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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H35F3O6
Molecular Weight 500.5477
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TRAVOPROST

SMILES

CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC2=CC(=CC=C2)C(F)(F)F

InChI

InChIKey=MKPLKVHSHYCHOC-AHTXBMBWSA-N
InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H35F3O6
Molecular Weight 500.5477
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analogue that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid. The travoporst free acid is potent and highly selective for the FP prostanoid receptor. Travoprost free acid is a selective FP prostanoid receptor agonist and is believed to reduce intraocular pressure by increasing the drainage of aqueous humor, which is done primarily through increased uveoscleral outflow and to a lesser extent, trabecular outflow facility. Travoprost ophthalmic solution is used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication. Travoprost is known by the brand names of Travatan and Travatan Z, manufactured by Alcon.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.4 nM [EC50]
49.9 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRAVATAN Z
Primary
Unknown
Preventing
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
0.049 ng/mL
1 drop 1 times / day multiple, ocular
FLUPROSTENOL plasma
Homo sapiens
0.018 ng/mL
1 drop 1 times / day multiple, ocular
FLUPROSTENOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.039 ng × h/mL
1 drop 1 times / day multiple, ocular
FLUPROSTENOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
31.8 min
1 drop 1 times / day multiple, ocular
FLUPROSTENOL plasma
Homo sapiens
45 min
1 drop 1 times / day multiple, ocular
FLUPROSTENOL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
FLUPROSTENOL plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Mare: single dose - 263 ug in 5 ml
Route of Administration: Intramuscular
In Vitro Use Guide
FP-receptor-mediated phosphoinositide (PI) turnover and [Ca(2+)](i) mobilization were measured in human trabecular meshwork (h-TM) cells by determining the accumulation of [(3)H]-inositol phosphates ([(3)H]-IPs). Travoprost acid concentration-dependently stimulated production of [(3)H]-IPs in h-TM cells with the following agonist potency EC(50) = 2.4 nM
Substance Class Chemical
Record UNII
WJ68R08KX9
Record Status Validated (UNII)
Record Version