Page last updated: 2024-12-10

fluprostenol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

fluprostenol: synthetic prostaglandin F 2 alpha analog used as an abortifacient; RN given refers to ((1alpha(Z),2beta(1E,3R*),3alpha,5alpha)-(+-))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

fluprostenol : An organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5311100
CHEMBL ID1201379
CHEBI ID60782
SCHEMBL ID230607
MeSH IDM0048846

Synonyms (76)

Synonym
BRD-K31611373-001-02-7
travoprost acid
CHEBI:60782 ,
rac-(5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-{(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl}cyclopentyl]hept-5-enoic acid
fluprostenolum
travoprost free acid
gtpl1940
IDI1_033806
BSPBIO_001336
fluprostenol
NCGC00160386-01
NCGC00160386-02
einecs 255-029-3
fluprostenol [inn:ban]
ici 81,008
fluprostenolum [inn-latin]
NCGC00160386-04
HMS1989C18
40666-16-8
BML2-G08
HMS1791C18
HMS1361C18
(5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid
(z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoic acid
NCGC00160386-05
ici-81008
fluoprostenol
CHEMBL1201379
dtxcid5026122
tox21_111778
dtxsid7046122 ,
cas-40666-16-8
358s7vue5n ,
unii-358s7vue5n
(+)-fluprostenol
54276-17-4
fluprostenol, (+)-
unii-meh3mce8x1
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)-
(5z ,13e )-(9s,11r,15r )-9,11,15-trihydroxy-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-5,13-prostadienoic acid
meh3mce8x1 ,
16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranorprostaglandin f2alpha
al-5848
[3h](+)-fluprostenol
(5z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(1e,3r)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
gtpl3417
[3h]-(+)-fluprostenol
16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranorprostaglandin f2.alpha.
SCHEMBL230607
5-heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-(1.alpha.(z),2.beta.(1e,3r*),3.alpha.,5.alpha.)-,(+/-)-
fluprostenol [inn]
fluprostenol [mi]
(+/-)-(z)-7-((1r*,2r*,3r*,5s*)-3,5-dihydroxy-2-((e)-(3r*)-3-hydroxy-4-((.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate
ici 80,008 free acid
5-heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, (1.alpha.(z),2.beta.(1e,3r*),3.alpha.,5.alpha.)-
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)-rel-
(+/-)-fluprostenol
ici-80008 free acid
(z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((r,e)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoic acid
(5z)-7-((1r,2r,3r,5s)-2-((r,e)-4-(3-(trifluoromethyl)phenoxy)-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid
(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
AKOS024458212
HMS3648H08
HMS3402C18
bdbm50206025
fluprostenol travoprost acid
DB11519
Q27077691
sr-01000946504
SR-01000946504-1
[1r-[1alpha(z),2beta(1e,3r*),3alpha,5alpha]]-7-[3,5-dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid
MS-28380
HY-108560
EX-A3612
BT176360
CS-0029169

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment with fluprostenol or combined fluprostenol/CTGF induced the activity of matrix metalloproteinase 2 (MMP2) in TM cells, whereas treatment with CTGF alone had no effects on MMP2 activity."( The prostaglandin f2α analog fluprostenol attenuates the fibrotic effects of connective tissue growth factor on human trabecular meshwork cells.
Fuchshofer, R; Junglas, B; Kuespert, S; Tamm, ER,
)
0.76

Toxicity

ExcerptReferenceRelevance
" This is a significant limitation because sustained changes in blood pressure are often accompanied by changes in heart rate and together can lead to cardiac hypertrophy and myocardial degeneration in animals, and major adverse cardiovascular events (MACE) in humans."( Natriuretic Peptides as Cardiovascular Safety Biomarkers in Rats: Comparison With Blood Pressure, Heart Rate, and Heart Weight.
Engle, SK; Watson, DE, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" U-46619 evoked a sharp decrease in microvessel diameter within a 10(-7)-10(-4)M gamut, with the dose-response profiles at 5- and 10-min timepoints remaining essentially parallel over the tested range of concentrations."( Vascular activities of prostaglandins and selective prostanoid receptor agonists in human retinal microvessels.
Nieves, AL; Spada, CS; Woodward, DF, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
antiglaucoma drugAny drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
prostaglandin receptor agonistAn agonist that binds to and activates prostaglandin receptors.
female contraceptive drugA chemical substance or agent with contraceptive activity in females.
abortifacientA chemical substance that interrupts pregnancy after implantation.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
prostaglandins Falpha
hydroxy monocarboxylic acidAny monocarboxylic acid which also contains a separate (alcoholic or phenolic) hydroxy substituent.
(trifluoromethyl)benzenesAn organofluorine compound that is (trifluoromethyl)benzene and derivatives arising from substitution of one or more of the phenyl hydrogens.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.04470.003245.467312,589.2998AID2517
AR proteinHomo sapiens (human)Potency23.91450.000221.22318,912.5098AID743036
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency2.39140.000214.376460.0339AID720691
estrogen nuclear receptor alphaHomo sapiens (human)Potency20.05430.000229.305416,493.5996AID743069; AID743075; AID743080
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin F2-alpha receptorHomo sapiens (human)EC50 (µMol)0.00360.00360.07620.2500AID1331417
Prostaglandin E2 receptor EP3 subtypeHomo sapiens (human)EC50 (µMol)3.40000.00252.54055.0000AID1331418
Prostacyclin receptorHomo sapiens (human)EC50 (µMol)10.00000.00040.05450.3470AID1331419
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayProstaglandin F2-alpha receptorHomo sapiens (human)
parturitionProstaglandin F2-alpha receptorHomo sapiens (human)
positive regulation of cell population proliferationProstaglandin F2-alpha receptorHomo sapiens (human)
positive regulation of gene expressionProstaglandin F2-alpha receptorHomo sapiens (human)
response to estradiolProstaglandin F2-alpha receptorHomo sapiens (human)
response to lipopolysaccharideProstaglandin F2-alpha receptorHomo sapiens (human)
negative regulation of apoptotic processProstaglandin F2-alpha receptorHomo sapiens (human)
cellular response to prostaglandin D stimulusProstaglandin F2-alpha receptorHomo sapiens (human)
inflammatory responseProstaglandin F2-alpha receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin F2-alpha receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin F2-alpha receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
cell deathProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
positive regulation of fever generationProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
intestine smooth muscle contractionProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
negative regulation of gastric acid secretionProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerProstacyclin receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstacyclin receptorHomo sapiens (human)
cell-cell signalingProstacyclin receptorHomo sapiens (human)
negative regulation of platelet-derived growth factor receptor signaling pathwayProstacyclin receptorHomo sapiens (human)
response to lipopolysaccharideProstacyclin receptorHomo sapiens (human)
negative regulation of smooth muscle cell proliferationProstacyclin receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstacyclin receptorHomo sapiens (human)
inflammatory responseProstacyclin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
prostaglandin F receptor activityProstaglandin F2-alpha receptorHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
guanyl-nucleotide exchange factor activityProstacyclin receptorHomo sapiens (human)
prostacyclin receptor activityProstacyclin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionProstaglandin F2-alpha receptorHomo sapiens (human)
cytoplasmProstaglandin F2-alpha receptorHomo sapiens (human)
plasma membraneProstaglandin F2-alpha receptorHomo sapiens (human)
plasma membraneProstaglandin F2-alpha receptorHomo sapiens (human)
nuclear envelopeProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
cytosolProstacyclin receptorHomo sapiens (human)
plasma membraneProstacyclin receptorHomo sapiens (human)
plasma membraneProstacyclin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1346343Human EP3 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346394Human FP receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346425Mouse FP receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346422Human TP receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1331417Agonist activity at human prostaglandin FP receptor expressed in CHO cells assessed as increase in intracellular calcium level by Fura 2-AM dye based fluorescence assay2017ACS medicinal chemistry letters, Jan-12, Volume: 8, Issue:1
Discovery of Novel Seven-Membered Prostacyclin Analogues as Potent and Selective Prostaglandin FP and EP3 Dual Agonists.
AID1331419Agonist activity at human IP receptor expressed in CHO cells assessed as increase in intracellular cAMP level by HTRF method2017ACS medicinal chemistry letters, Jan-12, Volume: 8, Issue:1
Discovery of Novel Seven-Membered Prostacyclin Analogues as Potent and Selective Prostaglandin FP and EP3 Dual Agonists.
AID1331418Agonist activity at human EP3 receptor expressed in CHO cells assessed as increase in intracellular calcium level by Fura 2-AM dye based fluorescence assay2017ACS medicinal chemistry letters, Jan-12, Volume: 8, Issue:1
Discovery of Novel Seven-Membered Prostacyclin Analogues as Potent and Selective Prostaglandin FP and EP3 Dual Agonists.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (94)

TimeframeStudies, This Drug (%)All Drugs %
pre-199025 (26.60)18.7374
1990's20 (21.28)18.2507
2000's31 (32.98)29.6817
2010's14 (14.89)24.3611
2020's4 (4.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.62

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.62 (24.57)
Research Supply Index4.61 (2.92)
Research Growth Index4.43 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.02%)5.53%
Reviews2 (2.04%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other95 (96.94%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]