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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H29F3O6
Molecular Weight 458.468
Optical Activity ( + )
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of FLUPROSTENOL, (+)-

SMILES

O[C@@H](COC1=CC(=CC=C1)C(F)(F)F)\C=C\[C@H]2[C@H](O)C[C@H](O)[C@@H]2C\C=C/CCCC(O)=O

InChI

InChIKey=WWSWYXNVCBLWNZ-QIZQQNKQSA-N
InChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1

HIDE SMILES / InChI
Molecular Formula C23H29F3O6
Molecular Weight 458.468
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.

Originator

Approval Year

2001
194
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 1.4 nM [EC50]
Agonist
2678
 49.9 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Infertility
14
Sources: DOI: 10.1080/00480169.1974.34145 https://www.ncbi.nlm.nih.gov/pubmed/6911921
 Primary
Preclinical
Unknown

Approved Use

Unknown
Preventing
Preclinical
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.018 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021994lbl.pdf
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28437175
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28437175
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021994lbl.pdf
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28437175
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%
REVIEW
https://www.ema.europa.eu/en/documents/scientific-discussion/travatan-epar-scientific-discussion_en.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/25259759
unhealthy
n = 1
Health Status: unhealthy
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/25259759
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:
https://pubmed.ncbi.nlm.nih.gov/25259759
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
Disc. AE: Conjunctival hyperemia...
AEs leading to
discontinuation/dose reduction:
Conjunctival hyperemia (3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/25259759
unhealthy
n = 1
Health Status: unhealthy
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/25259759
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:
https://pubmed.ncbi.nlm.nih.gov/25259759
unhealthy
n = 1
Health Status: unhealthy
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/25259759
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
unhealthy
n = 336
Health Status: unhealthy
Population Size: 336
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
esterase
72
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
esterase
72
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:746859
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:746859
ChemicalBook
CB5703458
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5703458
MolPort
MolPort-006-167-507
https://www.molport.com/shop/molecule-link/MolPort-006-167-507
ZINC
ZINC000004474682
http://zinc15.docking.org/substances/ZINC000004474682
eMolecules
26757104
https://www.emolecules.com/cgi-bin/more?vid=26757104
PubMed

PubMed

TitleDatePubMed
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
2000 Jan 17
Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study.
2008 May
A case of melancholic depression induced by beta-blocker antiglaucoma agents.
2008 Oct 6
Outcome of raised intraocular pressure in uveitic eyes with and without a corticosteroid-induced hypertensive response.
2009 Aug
Pharmacotherapy of intraocular pressure - part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides.
2009 Dec
Patents

Patents

021994-001
3
US20040198817
3
US5665773
3
US8178582
3
WO2013093528A1
3

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Sat Dec 16 09:17:01 GMT 2023
Edited
by admin
on Sat Dec 16 09:17:01 GMT 2023
Record UNII
MEH3MCE8X1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUPROSTENOL, (+)-
Common Name English
TRAVOPROST RELATED COMPOUND A [USP IMPURITY]
Common Name English
(+)-FLUPROSTENOL
Common Name English
(5Z ,13E )-(9S,11R,15R )-9,11,15-TRIHYDROXY-16-(M-TRIFLUOROMETHYLPHENOXY)-17,18,19,20-TETRANOR-5,13-PROSTADIENOIC ACID
Common Name English
AL-5848
Code English
16-(M-TRIFLUOROMETHYLPHENOXY)-17,18,19,20-TETRANORPROSTAGLANDIN F2.ALPHA.
Systematic Name English
TRAVOPROST ACID
Common Name English
TRAVOPROST RELATED COMPOUND A [USP-RS]
Common Name English
5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3R)-3-HYDROXY-4-(3-(TRIFLUOROMETHYL)PHENOXY)-1-BUTEN-1-YL)CYCLOPENTYL)-, (5Z)-
Systematic Name English
TRAVOPROST RELATED COMPOUND A
Common Name English
Code System Code Type Description
CAS
54276-17-4
Created by admin on Sat Dec 16 09:17:01 GMT 2023 , Edited by admin on Sat Dec 16 09:17:01 GMT 2023
PRIMARY
PUBCHEM
5311100
Created by admin on Sat Dec 16 09:17:01 GMT 2023 , Edited by admin on Sat Dec 16 09:17:01 GMT 2023
PRIMARY
RS_ITEM_NUM
1673012
Created by admin on Sat Dec 16 09:17:01 GMT 2023 , Edited by admin on Sat Dec 16 09:17:01 GMT 2023
PRIMARY
DRUG BANK
DBMET02216
Created by admin on Sat Dec 16 09:17:01 GMT 2023 , Edited by admin on Sat Dec 16 09:17:01 GMT 2023
PRIMARY
FDA UNII
MEH3MCE8X1
Created by admin on Sat Dec 16 09:17:01 GMT 2023 , Edited by admin on Sat Dec 16 09:17:01 GMT 2023
PRIMARY
CHEBI
60782
Created by admin on Sat Dec 16 09:17:01 GMT 2023 , Edited by admin on Sat Dec 16 09:17:01 GMT 2023
PRIMARY
Related Record Type Details
Structure of FLUPROSTENOL
RACEMATE -> ENANTIOMER
PROSTAGLANDIN F2-ALPHA RECEPTOR
TARGET -> AGONIST
Related Record Type Details
Structure of TRAVOPROST
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of TRAVOPROST
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of FLUPROSTENOL, (+)-
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC TOPICAL OCULAR ADMINISTRATION

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