U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00287doi: 10.1080/00480169.1974.34145
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/12490597 | https://www.ncbi.nlm.nih.gov/pubmed/8921038

(+)-Fluprostenol is the optically active enantiomer of fluprostenol. It is a potent and highly selective prostaglandin F2-alpha (FP) receptor agonist. (+)-Fluprostenol corrected corpora lutea persistence in the mares without significant clinical side effects. It was also an effective at inducing parturition in alpacas.

Approval Year

TargetsConditions

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

2006
Sources: DOI: 10.1080/00480169.1974.34145 https://www.ncbi.nlm.nih.gov/pubmed/6911921
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
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
Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction.
2008 Nov
Prostanoids for the management of glaucoma.
2008 Nov
Niacin promotes adipogenesis by reducing production of anti-adipogenic PGF2α through suppression of C/EBPβ-activated COX-2 expression.
2011 Apr
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:36:48 GMT 2023
Edited
by admin
on Fri Dec 15 16:36:48 GMT 2023
Record UNII
WJ68R08KX9
Record Status Validated (UNII)
Record Version
  • Download
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 [WHO-DD]
Common Name English
TRAVOPROST [MI]
Common Name English
AL-6221
Code 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 Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
EMA ASSESSMENT REPORTS TRAVATAN (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
WHO-VATC QS01EE04
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
EMA ASSESSMENT REPORTS DUOTRAV (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
WHO-ATC S01EE04
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
EMA ASSESSMENT REPORTS IZBA (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
NCI_THESAURUS C29705
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
EMA ASSESSMENT REPORTS IZBA (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
EMA ASSESSMENT REPORTS DUOTRAV (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
EMA ASSESSMENT REPORTS TRAVATAN (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
Code System Code Type Description
USAN
JJ-93
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
INN
7775
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
WIKIPEDIA
TRAVOPROST
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
CAS
157283-68-6
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
DRUG BANK
DB00287
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
EVMPD
SUB12613MIG
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
SMS_ID
100000089312
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
LACTMED
Travoprost
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
FDA UNII
WJ68R08KX9
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200799
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
DRUG CENTRAL
2716
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
DAILYMED
WJ68R08KX9
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
RS_ITEM_NUM
1673001
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
NCI_THESAURUS
C47766
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
IUPHAR
7102
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
RXCUI
283809
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID80896948
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
MERCK INDEX
m11008
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY Merck Index
CHEBI
746859
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
MESH
C438103
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
PUBCHEM
5282226
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
NSC
760366
Created by admin on Fri Dec 15 16:36:48 GMT 2023 , Edited by admin on Fri Dec 15 16:36:48 GMT 2023
PRIMARY
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