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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H35F3O6
Molecular Weight 500.5487
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(/[H])=C(/[H])\C[C@]1([H])[C@@]([H])(/C(/[H])=C(\[H])/[C@]([H])(COc2cccc(c2)C(F)(F)F)O)[C@@]([H])(C[C@]1([H])O)O

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

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_LBL.pdf

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRAVATAN Z

Approved Use

TRAVATAN Z® (travoprost ophthalmic solution) 0.004% is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

Launch Date

1.15871043E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.018 ng/mL
1 drop 1 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
FLUPROSTENOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.049 ng/mL
1 drop 1 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
FLUPROSTENOL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.039 ng × h/mL
1 drop 1 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
FLUPROSTENOL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
45 min
1 drop 1 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
FLUPROSTENOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
31.8 min
1 drop 1 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
FLUPROSTENOL plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
FLUPROSTENOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.004 % 1 times / 15 min multiple, ophthalmic
Overdose
Dose: 0.004 %, 1 times / 15 min
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / 15 min
Sources:
unhealthy
n = 1
Health Status: unhealthy
Sex: F
Population Size: 1
Sources:
Disc. AE: Abdominal cramps, Bleeding menstrual heavy...
AEs leading to
discontinuation/dose reduction:
Abdominal cramps (severe, 1 patient)
Bleeding menstrual heavy (severe, 1 patient)
Sources:
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
Disc. AE: Conjunctival hyperemia...
AEs leading to
discontinuation/dose reduction:
Conjunctival hyperemia (3%)
Sources:
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
Disc. AE: Hyperemia eye, Iritis...
AEs leading to
discontinuation/dose reduction:
Hyperemia eye (2 patients)
Iritis (1 patient)
Dermatitis (1 patient)
Upper respiratory infection (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Abdominal cramps severe, 1 patient
Disc. AE
0.004 % 1 times / 15 min multiple, ophthalmic
Overdose
Dose: 0.004 %, 1 times / 15 min
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / 15 min
Sources:
unhealthy
n = 1
Health Status: unhealthy
Sex: F
Population Size: 1
Sources:
Bleeding menstrual heavy severe, 1 patient
Disc. AE
0.004 % 1 times / 15 min multiple, ophthalmic
Overdose
Dose: 0.004 %, 1 times / 15 min
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / 15 min
Sources:
unhealthy
n = 1
Health Status: unhealthy
Sex: F
Population Size: 1
Sources:
Conjunctival hyperemia 3%
Disc. AE
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
Dermatitis 1 patient
Disc. AE
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
Iritis 1 patient
Disc. AE
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
Upper respiratory infection 1 patient
Disc. AE
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
Hyperemia eye 2 patients
Disc. AE
0.004 % 1 times / day multiple, ophthalmic
Recommended
Dose: 0.004 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.004 %, 1 times / day
Sources:
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol.
2004 Aug
Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study.
2008 May
Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction.
2008 Nov
A case of melancholic depression induced by beta-blocker antiglaucoma agents.
2008 Oct 6
Patents

Sample Use Guides

The recommended dosage is one drop in the affected eye(s) once daily in the evening. TRAVATAN Z® (travoprost ophthalmic solution) should not be administered more than once daily
Route of Administration: Topical
Travoprost stimulated the contraction of isolated non-pregnant female rat uterus in a concentration-dependent manner with the agonist potency EC(50)=1.3+/-0.07 nM
Name Type Language
TRAVOPROST
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
TRAVOPROST [INN]
Common Name English
TRAVOPROST [JAN]
Common Name English
TRAVOPROST [ORANGE BOOK]
Common Name English
TRAVOPROST [USP MONOGRAPH]
Common Name English
TRAVATAN
Brand Name English
NSC-760366
Code English
ISOPROPYL (Z)-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3R)-3-HYDROXY-4-((.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)OXY)-1-BUTENYL)CYCLOPENTYL)-5-HEPTENOATE
Systematic Name English
IZBA
Brand Name English
TRAVOPROST [MART.]
Common Name English
(1R-(1.ALPHA.(Z),2.BETA.(1E,3R*),3.ALPHA.,5.ALPHA.))-7-(3,5-DIHYDROXY-2-(3-HYDROXY-4-(3-(TRIFLUOROMETHYL)PHENOXY)-1-BUTENYL)CYCLOPENTYL)-5-HEPTENOIC ACID, 1-METHYLETHYL ESTER
Common Name English
TRAVOPROST [VANDF]
Common Name English
TRAVOPROST COMPONENT OF DUOTRAV
Brand Name English
TRAVOPROST [USAN]
Common Name English
TRAVOPROST [MI]
Common Name English
AL-6221
Code English
TRAVOPROST [WHO-DD]
Common Name English
OTX-TP
Common Name English
DUOTRAV COMPONENT TRAVOPROST
Brand Name English
TRAVOPROST [USP-RS]
Common Name English
TRAVOPROST [EMA EPAR]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175454
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
EMA ASSESSMENT REPORTS TRAVATAN (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
NCI_THESAURUS C78568
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
WHO-VATC QS01EE04
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
EMA ASSESSMENT REPORTS DUOTRAV (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
WHO-ATC S01EE04
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
EMA ASSESSMENT REPORTS IZBA (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
NDF-RT N0000007706
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
NDF-RT N0000007706
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
NCI_THESAURUS C29705
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
EMA ASSESSMENT REPORTS IZBA (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
NDF-RT N0000007706
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
EMA ASSESSMENT REPORTS DUOTRAV (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
EMA ASSESSMENT REPORTS TRAVATAN (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
Code System Code Type Description
INN
7775
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
WIKIPEDIA
TRAVOPROST
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
CAS
157283-68-6
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
DRUG BANK
DB00287
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
EVMPD
SUB12613MIG
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
LACTMED
Travoprost
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
FDA UNII
WJ68R08KX9
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200799
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
DRUG CENTRAL
2716
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
NCI_THESAURUS
C47766
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
IUPHAR
7102
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
RXCUI
283809
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M11008
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1673001
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY USP-RS
MESH
C438103
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY
PUBCHEM
5282226
Created by admin on Fri Jun 25 21:01:59 UTC 2021 , Edited by admin on Fri Jun 25 21:01:59 UTC 2021
PRIMARY