Page last updated: 2024-12-07

fr 139317

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Description

FR 139317: endothelin receptor A antagonist; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID107810
CHEMBL ID352396
SCHEMBL ID2124350
MeSH IDM0212979

Synonyms (29)

Synonym
d-alanine, n-((hexahydro-1h-azepin-1-yl)carbonyl)-l-leucyl-1-methyl-d-tryptophyl-3-(2-pyridinyl)-
fr 139317
d-alanine, n-(n-(n-((hexahydro-1h-azepin-1-yl)carbonyl)-l-leucyl)-1-methyl-d-tryptophyl)-3-(2-pyridinyl)-
2-((1-(hexahydro-1h-azepinyl)carbonyl)amino-4-methylpentanoyl)-3-(-(1-methyl-1h-indolyl)propionyl)amino-3-(2-pyridyl)propionic acid
gtpl998
tocris-1210
NCGC00025042-01
fr139317
NCGC00025042-02
bdbm50286804
CHEMBL352396 ,
(2r)-2-[[(2r)-2-[[(2s)-2-(azepane-1-carbonylamino)-4-methylpentanoyl]amino]-3-(1-methylindol-3-yl)propanoyl]amino]-3-pyridin-2-ylpropanoic acid
(r)-2-[(r)-2-{(s)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoylamino}-3-(1-methyl-1h-indol-3-yl)-propionylamino]-3-pyridin-2-yl-propionic acid
142375-60-8
SCHEMBL2124350
F-180 ,
n-[n-[n-[(hexahydro-1h-azepin-1-yl)carbonyl]-l-leucyl]-1-methyl-d-tryptophyl]-3-(2-pyridinyl)-d-alanine
AKOS024456467
sr-01000597371
SR-01000597371-1
(2r)-2-{[(2r)-2-({(2s)-2-[(1-azepanylcarbonyl)amino]-4-methylpentanoyl}amino)-3-(1-methyl-1h-indol-3-yl)propanoyl]amino}-3-(2-pyridinyl)propanoic acid
(r)-2-((r)-2-((s)-2-(azepane-1-carboxamido)-4-methylpentanamido)-3-(1-methyl-1h-indol-3-yl)propanamido)-3-(pyridin-2-yl)propanoic acid
HMS3676O03
n-{2-[(2-{[(azepan-1-yl)(hydroxy)methylidene]amino}-1-hydroxy-4-methylpentylidene)amino]-1-hydroxy-3-(1-methyl-1h-indol-3-yl)propylidene}-3-pyridin-2-ylalanine
DTXSID30931419
Q27077729
HMS3412O03
(2r)-2-[[(2r)-2-[[(2s)-2-(azepane-1-carbonylamino)-4-methylpentanoyl]amino]-3-(1-methylindol-3-yl)propanoyl]amino]-3-pyridin-2-ylpropanoic acid.
d-alanine,n-[(hexahydro-1h-azepin-1-yl)carbonyl]-l-leucyl-1-methyl-d-tryptophyl-3-(2-pyridinyl)-

Research Excerpts

Overview

FR 139317 seems to be a selective ETA-receptor antagonist which competitively antagonizes the endothelin-1- and endothelins-2-induced contractions of guinea-pig isolated pulmonary arteries.

ExcerptReferenceRelevance
"5. FR 139317 seems to be a selective ETA-receptor antagonist which competitively antagonizes the endothelin-1- and endothelin-2-induced contractions of guinea-pig isolated pulmonary arteries."( A novel ETA-receptor antagonist, FR 139317, inhibits endothelin-induced contractions of guinea-pig pulmonary arteries, but not trachea.
Cardell, LO; Edvinsson, L; Uddman, R, 1993
)
1.08

Treatment

ExcerptReferenceRelevance
"Pre-treatment with FR 139317 (i.v."( Role of endothelin ET(A)- and ET(B)-receptors in haemodynamic compensation following haemorrhage in anaesthetized rats.
Lim, SL; Palacios, B; Pang, CC, 2002
)
0.63

Bioavailability

ExcerptReferenceRelevance
" Comparison of urea 2 with a series of well-absorbed compounds using delta log P analysis suggested that 2 has an excess capacity for forming hydrogen bonds with solvent."( Azole endothelin antagonists. 3. Using delta log P as a tool to improve absorption.
Calzadilla, SV; Chiou, W; Dayton, BD; Dixon, DB; Hernandez, L; Hoffman, DJ; Kester, JA; Marsh, KC; Nellans, HN; Opgenorth, TJ; von Geldern, TW; Wu-Wong, JR, 1996
)
0.29

Dosage Studied

ExcerptRelevanceReference
" A dose-response curve for response to ET-1 was plotted for cumulative concentrations (from 10(-11) to 10(-8) mol/l) in the presence and absence of 10(-6) mol/l FR 139317 (a selective antagonist of ET(A) receptors)."( The vasoconstriction induced by endothelin-1 is mediated only by ET(A) receptors in mesenteric small resistance arteries of spontaneously hypertensive rats and Wistar Kyoto rats.
Agabiti-Rosei, E; Bettoni, G; Castellano, M; Pasini, G; Piccoli, A; Porteri, E; Rizzoni, D, 1997
)
0.49
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (24)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID886
Chain A, CruzipainTrypanosoma cruziPotency15.84890.002014.677939.8107AID1476
cytochrome P450 2C9 precursorHomo sapiens (human)Potency6.30960.00636.904339.8107AID883
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency15.84890.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency31.62280.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency6.30960.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
sialic acid transportSialinHomo sapiens (human)
monoatomic ion transportSialinHomo sapiens (human)
amino acid transportSialinHomo sapiens (human)
response to bacteriumSialinHomo sapiens (human)
carbohydrate transmembrane transportSialinHomo sapiens (human)
D-glucuronate transmembrane transportSialinHomo sapiens (human)
proton transmembrane transportSialinHomo sapiens (human)
sialic acid transportSialinHomo sapiens (human)
monoatomic anion transportSialinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
carbohydrate:proton symporter activitySialinHomo sapiens (human)
sialic acid transmembrane transporter activitySialinHomo sapiens (human)
sialic acid:proton symporter activitySialinHomo sapiens (human)
D-glucuronate transmembrane transporter activitySialinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
lysosomal membraneSialinHomo sapiens (human)
cytosolSialinHomo sapiens (human)
plasma membraneSialinHomo sapiens (human)
membraneSialinHomo sapiens (human)
basolateral plasma membraneSialinHomo sapiens (human)
synaptic vesicle membraneSialinHomo sapiens (human)
plasma membraneSialinHomo sapiens (human)
lysosomeSialinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1669242Lipophilicity, log Pof the compound2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.
AID1669241Inhibition of human recombinant-Sialin expressed in HEK293 cells assessed as reduction in [3H]Neu5Ac transport pre-incubated for 15 mins at pH 5.5 followed by 15 mins wash at pH 7 at room temperature by liquid scintillation counting method relative to con2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.
AID1669224Ratio of Km for Neu5Ac to Ic50 for test compound for inhibition of human recombinant-Sialin expressed in HEK293 cells assessed as reduction in [3H]Neu5Ac uptake at 30 to 300 uM incubated for 15 mins by liquid scintillation counting method2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.
AID1669222Inhibition of human recombinant-Sialin expressed in HEK293 cells assessed as reduction in [3H]Neu5Ac uptake at 30 to 300 uM incubated for 15 mins by liquid scintillation counting method2020Journal of medicinal chemistry, 08-13, Volume: 63, Issue:15
Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.
AID1345905Human ETA receptor (Endothelin receptors)1995British journal of pharmacology, May, Volume: 115, Issue:1
ETA receptor-mediated constrictor responses to endothelin peptides in human blood vessels in vitro.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (217)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's166 (76.50)18.2507
2000's42 (19.35)29.6817
2010's6 (2.76)24.3611
2020's3 (1.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.78

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.78 (24.57)
Research Supply Index5.39 (2.92)
Research Growth Index4.17 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (1.37%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other216 (98.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]