Page last updated: 2024-11-07

5-(dimethylamino)-n-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide

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Description

5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide: structure in first source; endothelin receptor antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122272
CHEMBL ID267458
CHEBI ID92993
SCHEMBL ID802730
MeSH IDM0227512

Synonyms (25)

Synonym
5-dimethylamino-naphthalene-1-sulfonic acid (3,4-dimethyl-isoxazol-5-yl)-amide
5-dimethylamino-naphthalene-1-sulfonic acid (3,4-dimethyl-2,3-dihydro-oxazol-5-yl)-amide
5-dimethylamino-naphthalene-1-sulfonic acid (3,4-dimethyl-isoxazol-5-yl)-amide (bms 182874)
bdbm50034435
tocris-1441
NCGC00025164-01
bms-182874
5-ddins
1-naphthalenesulfonamide, 5-(dimethylamino)-n-(3,4-dimethyl-5-isoxazolyl)-
5-(dimethylamino)-n-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide
bms 182874
153042-42-3
L009159
CHEMBL267458 ,
5-(dimethylamino)-n-(3,4-dimethyl-1,2-oxazol-5-yl)naphthalene-1-sulfonamide
BRD-K56509348-003-01-3
SCHEMBL802730
DTXSID60165205
CHEBI:92993
Q27164725
5-(dimethylamino)-n-(3,4-dimethylisoxazol-5-yl)naphthalene-1-sulfonamide
E87723
HY-118497
CS-0066140
AKOS040748001

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic parameters were obtained after an intravenous and a range of oral doses of BMS-182874 in rats."( Pharmacokinetics and metabolism of endothelin receptor antagonist: contribution of kidneys in the overall in vivo N-demethylation.
Chong, S; Humphreys, WG; Obermeier, M, 2003
)
0.32

Bioavailability

ExcerptReferenceRelevance
" The compound has 70% oral bioavailability in rats."( 2,4-Diarylpyrrolidine-3-carboxylic acids--potent ETA selective endothelin receptor antagonists. 1. Discovery of A-127722.
Bal, R; Boyd, SA; Chiou, WJ; Dixon, DB; Hernandez, L; Jae, HS; Kester, JA; Mantei, RA; Marsh, KC; Novosad, EI; Opgenorth, TJ; Sorensen, BK; Tasker, AS; von Geldern, TW; Winn, M; Wu-Wong, JR, 1996
)
0.29
" Saturable first-pass metabolism and the role of extrahepatic tissue were evaluated as possible reasons for complete oral bioavailability despite extensive metabolic clearance."( Pharmacokinetics and metabolism of endothelin receptor antagonist: contribution of kidneys in the overall in vivo N-demethylation.
Chong, S; Humphreys, WG; Obermeier, M, 2003
)
0.32

Dosage Studied

ExcerptRelevanceReference
" An identical dosage regimen of BQ-123 did not exhibit significant vasculoprotection (neointima:media ratio of 128% vehicle control)."( Endothelin receptor subtypes in the pathogenesis of angioplasty-induced neointima formation in the rat: a comparison of selective ETA receptor antagonism and dual ETA/ETB receptor antagonism using BQ-123 and SB 209670.
Douglas, SA; Elliott, JD; Louden, C; Ohlstein, EH; Vickery-Clark, LM, 1995
)
0.29
" When dosed orally at 10 mg/kg to conscious, normotensive rats infused with big ET-1, compounds such as 7m showed significant inhibition of the pressor response with a duration of effect lasting for the 5-h course of the experiment."( New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
Bath, C; Bradbury, RH; Butlin, RJ; Dennis, M; Heys, C; Hunt, SJ; James, R; Mortlock, AA; Sumner, NF; Tang, EK; Telford, B; Whiting, E; Wilson, C, 1997
)
0.3
" The suitability and robustness of the method for in vivo samples were confirmed by analysis of BMS from mouse plasma and tissues dosed with BMS."( Determination of endothelin antagonist BMS182874 in plasma by high-performance liquid chromatography.
Chavanpatil, MD; Gulati, A; Rajeshkumar, NV, 2006
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
sulfonic acid derivative
[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 (32)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency39.81070.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency35.48130.177814.390939.8107AID2147
phosphopantetheinyl transferaseBacillus subtilisPotency50.11870.141337.9142100.0000AID1490
USP1 protein, partialHomo sapiens (human)Potency44.66840.031637.5844354.8130AID504865
thyroid stimulating hormone receptorHomo sapiens (human)Potency15.84890.001318.074339.8107AID926; AID938
cytochrome P450 2C9 precursorHomo sapiens (human)Potency0.63100.00636.904339.8107AID883
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency39.81070.001815.663839.8107AID894
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency25.11890.354828.065989.1251AID504847
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency19.95260.031610.279239.8107AID884; AID885
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency28.18380.251215.843239.8107AID504327
lethal factor (plasmid)Bacillus anthracis str. A2012Potency12.58930.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency0.63100.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
[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)
Endothelin receptor type BHomo sapiens (human)Ki50.00000.00010.05430.3710AID66691; AID66692
Endothelin-1 receptorHomo sapiens (human)IC50 (µMol)0.23000.00000.76479.9000AID66341; AID68499; AID68661; AID68662
Endothelin-1 receptorHomo sapiens (human)Ki0.05150.00000.430010.0000AID68473; AID68488; AID68489; AID68659
Endothelin-1 receptorRattus norvegicus (Norway rat)IC50 (µMol)0.01500.00001.774610.0000AID66057
Endothelin-1 receptorRattus norvegicus (Norway rat)Ki200.00000.00000.00210.0065AID66213
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (109)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIEndothelin receptor type BHomo sapiens (human)
neural crest cell migrationEndothelin receptor type BHomo sapiens (human)
positive regulation of protein phosphorylationEndothelin receptor type BHomo sapiens (human)
renin secretion into blood streamEndothelin receptor type BHomo sapiens (human)
regulation of heart rateEndothelin receptor type BHomo sapiens (human)
regulation of pHEndothelin receptor type BHomo sapiens (human)
cell surface receptor signaling pathwayEndothelin receptor type BHomo sapiens (human)
negative regulation of adenylate cyclase activityEndothelin receptor type BHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEndothelin receptor type BHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEndothelin receptor type BHomo sapiens (human)
nervous system developmentEndothelin receptor type BHomo sapiens (human)
peripheral nervous system developmentEndothelin receptor type BHomo sapiens (human)
posterior midgut developmentEndothelin receptor type BHomo sapiens (human)
positive regulation of cell population proliferationEndothelin receptor type BHomo sapiens (human)
gene expressionEndothelin receptor type BHomo sapiens (human)
negative regulation of neuron maturationEndothelin receptor type BHomo sapiens (human)
response to organic cyclic compoundEndothelin receptor type BHomo sapiens (human)
vein smooth muscle contractionEndothelin receptor type BHomo sapiens (human)
calcium-mediated signalingEndothelin receptor type BHomo sapiens (human)
cGMP-mediated signalingEndothelin receptor type BHomo sapiens (human)
heparin metabolic processEndothelin receptor type BHomo sapiens (human)
melanocyte differentiationEndothelin receptor type BHomo sapiens (human)
regulation of fever generationEndothelin receptor type BHomo sapiens (human)
aldosterone metabolic processEndothelin receptor type BHomo sapiens (human)
enteric smooth muscle cell differentiationEndothelin receptor type BHomo sapiens (human)
positive regulation of urine volumeEndothelin receptor type BHomo sapiens (human)
renal sodium excretionEndothelin receptor type BHomo sapiens (human)
epithelial fluid transportEndothelin receptor type BHomo sapiens (human)
vasoconstrictionEndothelin receptor type BHomo sapiens (human)
vasodilationEndothelin receptor type BHomo sapiens (human)
negative regulation of apoptotic processEndothelin receptor type BHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionEndothelin receptor type BHomo sapiens (human)
macrophage chemotaxisEndothelin receptor type BHomo sapiens (human)
response to painEndothelin receptor type BHomo sapiens (human)
enteric nervous system developmentEndothelin receptor type BHomo sapiens (human)
regulation of epithelial cell proliferationEndothelin receptor type BHomo sapiens (human)
negative regulation of protein metabolic processEndothelin receptor type BHomo sapiens (human)
canonical Wnt signaling pathwayEndothelin receptor type BHomo sapiens (human)
positive regulation of penile erectionEndothelin receptor type BHomo sapiens (human)
establishment of endothelial barrierEndothelin receptor type BHomo sapiens (human)
renal sodium ion absorptionEndothelin receptor type BHomo sapiens (human)
calcium ion transmembrane transportEndothelin receptor type BHomo sapiens (human)
cellular response to lipopolysaccharideEndothelin receptor type BHomo sapiens (human)
protein transmembrane transportEndothelin receptor type BHomo sapiens (human)
podocyte differentiationEndothelin receptor type BHomo sapiens (human)
endothelin receptor signaling pathwayEndothelin receptor type BHomo sapiens (human)
renal albumin absorptionEndothelin receptor type BHomo sapiens (human)
neuroblast migrationEndothelin receptor type BHomo sapiens (human)
chordate pharynx developmentEndothelin receptor type BHomo sapiens (human)
response to sodium phosphateEndothelin receptor type BHomo sapiens (human)
response to endothelinEndothelin receptor type BHomo sapiens (human)
developmental pigmentationEndothelin receptor type BHomo sapiens (human)
mitotic cell cycleEndothelin-1 receptorHomo sapiens (human)
branching involved in blood vessel morphogenesisEndothelin-1 receptorHomo sapiens (human)
response to hypoxiaEndothelin-1 receptorHomo sapiens (human)
in utero embryonic developmentEndothelin-1 receptorHomo sapiens (human)
blood vessel remodelingEndothelin-1 receptorHomo sapiens (human)
response to amphetamineEndothelin-1 receptorHomo sapiens (human)
regulation of heart rateEndothelin-1 receptorHomo sapiens (human)
glomerular filtrationEndothelin-1 receptorHomo sapiens (human)
cardiac chamber formationEndothelin-1 receptorHomo sapiens (human)
left ventricular cardiac muscle tissue morphogenesisEndothelin-1 receptorHomo sapiens (human)
atrial cardiac muscle tissue developmentEndothelin-1 receptorHomo sapiens (human)
cardiac neural crest cell migration involved in outflow tract morphogenesisEndothelin-1 receptorHomo sapiens (human)
noradrenergic neuron differentiationEndothelin-1 receptorHomo sapiens (human)
intracellular calcium ion homeostasisEndothelin-1 receptorHomo sapiens (human)
smooth muscle contractionEndothelin-1 receptorHomo sapiens (human)
mitochondrion organizationEndothelin-1 receptorHomo sapiens (human)
signal transductionEndothelin-1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayEndothelin-1 receptorHomo sapiens (human)
activation of adenylate cyclase activityEndothelin-1 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayEndothelin-1 receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEndothelin-1 receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEndothelin-1 receptorHomo sapiens (human)
respiratory gaseous exchange by respiratory systemEndothelin-1 receptorHomo sapiens (human)
regulation of blood pressureEndothelin-1 receptorHomo sapiens (human)
cell population proliferationEndothelin-1 receptorHomo sapiens (human)
response to woundingEndothelin-1 receptorHomo sapiens (human)
gene expressionEndothelin-1 receptorHomo sapiens (human)
protein kinase A signalingEndothelin-1 receptorHomo sapiens (human)
regulation of glucose transmembrane transportEndothelin-1 receptorHomo sapiens (human)
neural crest cell fate commitmentEndothelin-1 receptorHomo sapiens (human)
artery smooth muscle contractionEndothelin-1 receptorHomo sapiens (human)
neuron remodelingEndothelin-1 receptorHomo sapiens (human)
heparin metabolic processEndothelin-1 receptorHomo sapiens (human)
thyroid gland developmentEndothelin-1 receptorHomo sapiens (human)
cellular response to oxidative stressEndothelin-1 receptorHomo sapiens (human)
embryonic heart tube developmentEndothelin-1 receptorHomo sapiens (human)
aorta developmentEndothelin-1 receptorHomo sapiens (human)
vasoconstrictionEndothelin-1 receptorHomo sapiens (human)
norepinephrine metabolic processEndothelin-1 receptorHomo sapiens (human)
middle ear morphogenesisEndothelin-1 receptorHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionEndothelin-1 receptorHomo sapiens (human)
cellular response to human chorionic gonadotropin stimulusEndothelin-1 receptorHomo sapiens (human)
enteric nervous system developmentEndothelin-1 receptorHomo sapiens (human)
sympathetic nervous system developmentEndothelin-1 receptorHomo sapiens (human)
axon extensionEndothelin-1 receptorHomo sapiens (human)
embryonic skeletal system developmentEndothelin-1 receptorHomo sapiens (human)
neuromuscular processEndothelin-1 receptorHomo sapiens (human)
sodium ion homeostasisEndothelin-1 receptorHomo sapiens (human)
canonical Wnt signaling pathwayEndothelin-1 receptorHomo sapiens (human)
face developmentEndothelin-1 receptorHomo sapiens (human)
axonogenesis involved in innervationEndothelin-1 receptorHomo sapiens (human)
establishment of endothelial barrierEndothelin-1 receptorHomo sapiens (human)
pharyngeal arch artery morphogenesisEndothelin-1 receptorHomo sapiens (human)
renal sodium ion absorptionEndothelin-1 receptorHomo sapiens (human)
calcium ion transmembrane transportEndothelin-1 receptorHomo sapiens (human)
cellular response to follicle-stimulating hormone stimulusEndothelin-1 receptorHomo sapiens (human)
cellular response to luteinizing hormone stimulusEndothelin-1 receptorHomo sapiens (human)
protein transmembrane transportEndothelin-1 receptorHomo sapiens (human)
glomerular endothelium developmentEndothelin-1 receptorHomo sapiens (human)
podocyte differentiationEndothelin-1 receptorHomo sapiens (human)
endothelin receptor signaling pathway involved in heart processEndothelin-1 receptorHomo sapiens (human)
renal albumin absorptionEndothelin-1 receptorHomo sapiens (human)
vascular associated smooth muscle cell developmentEndothelin-1 receptorHomo sapiens (human)
mesenchymal cell apoptotic processEndothelin-1 receptorHomo sapiens (human)
sympathetic neuron axon guidanceEndothelin-1 receptorHomo sapiens (human)
semaphorin-plexin signaling pathway involved in axon guidanceEndothelin-1 receptorHomo sapiens (human)
podocyte apoptotic processEndothelin-1 receptorHomo sapiens (human)
meiotic cell cycle process involved in oocyte maturationEndothelin-1 receptorHomo sapiens (human)
cranial skeletal system developmentEndothelin-1 receptorHomo sapiens (human)
response to acetylcholineEndothelin-1 receptorHomo sapiens (human)
regulation of protein localization to cell leading edgeEndothelin-1 receptorHomo sapiens (human)
positive regulation of cation channel activityEndothelin-1 receptorHomo sapiens (human)
endothelin receptor signaling pathwayEndothelin-1 receptorHomo sapiens (human)
developmental pigmentationEndothelin-1 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
endothelin receptor activityEndothelin receptor type BHomo sapiens (human)
protein bindingEndothelin receptor type BHomo sapiens (human)
peptide hormone bindingEndothelin receptor type BHomo sapiens (human)
type 1 angiotensin receptor bindingEndothelin receptor type BHomo sapiens (human)
phosphatidylinositol phospholipase C activityEndothelin-1 receptorHomo sapiens (human)
endothelin receptor activityEndothelin-1 receptorHomo sapiens (human)
protein bindingEndothelin-1 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneEndothelin receptor type BHomo sapiens (human)
nuclear membraneEndothelin receptor type BHomo sapiens (human)
plasma membraneEndothelin receptor type BHomo sapiens (human)
plasma membraneEndothelin-1 receptorHomo sapiens (human)
plasma membraneEndothelin-1 receptorHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (35)

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.
AID68661Ability to inhibit [125I]ET1 binding to vascular smooth muscle (vsm)- A10 cells1994Journal of medicinal chemistry, Feb-04, Volume: 37, Issue:3
The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.
AID25328Acidity constant was measured1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID68499Inhibition of specific binding of [125-I]ET-1 to human endothelin A receptor1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID66040Antagonism of ET-1 induced increase in intracellular Ca+2 in rabbit carotid artery rings1994Journal of medicinal chemistry, Feb-04, Volume: 37, Issue:3
The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.
AID68471Percent inhibition at 10 uM of displacement of radiolabeled endothelin-1 [125-I]ET-1 from membranes prepared from cloned human Endothelin A receptor expressed in mouse erythroleukemic (MEL) cells1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID66341Inhibitory concentration against Endothelin A receptor2004Journal of medicinal chemistry, Mar-11, Volume: 47, Issue:6
Selective optimization of side activities: another way for drug discovery.
AID184481Mean dose ratio(MDR) for inhibition of pressor response 3 hr after oral administration of compound at 10 mg/kg to conscious, normotensive rats1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID66213Selectivity for the ET-A receptor over ETB receptor was observed in rat cerebellar membranes1994Journal of medicinal chemistry, Feb-04, Volume: 37, Issue:3
The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.
AID66041Ability to inhibit Endothelin A receptor induced contractions in rabbit carotid artery rings (ETA) was determined in an in vitro functional assay.1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-bip
AID225828In vivo prevention of ET-1-induced sudden death in rats by pretreatment with endothelin receptor antagonist at a dose of 10 mg/kg p.o.; nd = not determined1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Discovery and optimization of a novel class of orally active nonpeptidic endothelin-A receptor antagonists.
AID184483Mean dose ratio(MDR) for inhibition of pressor response 5 hr after oral administration of compound at 10 mg/kg to conscious, normotensive rats1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID184479Mean dose ratio(MDR) for inhibition of pressor response 0.5 hr after oral administration of compound at 10 mg/kg to conscious, normotensive rats1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID66691Inhibitory activity against human Endothelin B receptor in chinese hamster ovary cells1996Journal of medicinal chemistry, Mar-01, Volume: 39, Issue:5
2,4-Diarylpyrrolidine-3-carboxylic acids--potent ETA selective endothelin receptor antagonists. 1. Discovery of A-127722.
AID166824Functional vascular ET-1 antagonism was determined in rabbit aorta rings with intact endothelium1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Discovery and optimization of a novel class of orally active nonpeptidic endothelin-A receptor antagonists.
AID68488Inhibitory activity against human Endothelin A receptor in chinese hamster ovary cells1996Journal of medicinal chemistry, Mar-01, Volume: 39, Issue:5
2,4-Diarylpyrrolidine-3-carboxylic acids--potent ETA selective endothelin receptor antagonists. 1. Discovery of A-127722.
AID66209Ability to inhibit binding of [125I]ET1 to membranes prepared from A10 rat thoracic aorta smooth muscle Endothelin A receptor1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-bip
AID68489Tested for binding affinity for human Endothelin A receptor by measuring its ability to displace [125I]-ET-1 from chinese hamster ovary cells(CHO)1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Pyrrolidine-3-carboxylic acids as endothelin antagonists. 3. Discovery of a potent, 2-nonaryl, highly selective ETA antagonist (A-216546).
AID22751Pharmacokinetic profile-half life was evaluated in rats upon intravenous administration1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Pyrrolidine-3-carboxylic acids as endothelin antagonists. 3. Discovery of a potent, 2-nonaryl, highly selective ETA antagonist (A-216546).
AID68659Binding affinity towards ET1 receptor was determined in A10 cells1994Journal of medicinal chemistry, Feb-04, Volume: 37, Issue:3
The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.
AID167575In vitro functional antagonistic testing by obtaining ET-1 concentration response curves in rabbit carotid artery rings in the presence or absence of antagonist.1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Discovery and structure-activity relationships of sulfonamide ETA-selective antagonists.
AID186747Antihypertensive activity administered orally at 100 uM was determined in vivo in rats1994Journal of medicinal chemistry, Feb-04, Volume: 37, Issue:3
The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.
AID68662Antagonism of ET-1 induced increase in intracellular Ca+2 in vsm-A10 cells1994Journal of medicinal chemistry, Feb-04, Volume: 37, Issue:3
The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.
AID68473Inhibition of Human Endothelin A receptor expressed in CHO Cells.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Biphenylsulfonamide endothelin receptor antagonists. 2. Discovery of 4'-oxazolyl biphenylsulfonamides as a new class of potent, highly selective ET(A) antagonists.
AID66692Tested for binding affinity for human Endothelin B receptor by measuring its ability to displace [125I]-ET-3 from chinese hamster ovary cells(CHO)1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Pyrrolidine-3-carboxylic acids as endothelin antagonists. 3. Discovery of a potent, 2-nonaryl, highly selective ETA antagonist (A-216546).
AID225109Ability to protect rats from ET-1 induced sudden death in rats after peroral administration1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Discovery and optimization of a novel class of orally active nonpeptidic endothelin-A receptor antagonists.
AID66201Inhibition of [125I]endothelin-l binding to endothelin A receptor of rat thoracic aorta smooth muscle cells1995Journal of medicinal chemistry, Feb-17, Volume: 38, Issue:4
Three-dimensional quantitative structure-activity relationships of sulfonamide endothelin inhibitors.
AID184482Mean dose ratio(MDR) for inhibition of pressor response 5 min after intravenous administration of compound at 10 mg/kg to pithed rats1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID18622Bioavailability in rat1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Pyrrolidine-3-carboxylic acids as endothelin antagonists. 3. Discovery of a potent, 2-nonaryl, highly selective ETA antagonist (A-216546).
AID184480Mean dose ratio(MDR) for inhibition of pressor response 1 hr after oral administration of compound at 10 mg/kg to conscious, normotensive rats1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
New non-peptide endothelin-A receptor antagonists: synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-,-N-pyrimidinyl-,-N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides.
AID225823In vivo prevention of ET-1-induced sudden death in 6 rats by pretreatment with endothelin receptor antagonist at a dose of 30 mg/kg p.o.1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Discovery and optimization of a novel class of orally active nonpeptidic endothelin-A receptor antagonists.
AID66057Antagonism of [125 I]ET-1 binding to the rat endothelin receptor in vascular smooth muscle VSM-A10 cells.1995Journal of medicinal chemistry, Apr-14, Volume: 38, Issue:8
Discovery and structure-activity relationships of sulfonamide ETA-selective antagonists.
AID67025Ability to inhibit binding of [125I]-ET-1 to membranes prepared from A10 rat cerebellum (Endothelin B receptor)1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-bip
AID225829In vivo prevention of ET-1-induced sudden death in rats by pretreatment with endothelin receptor antagonist at a dose of 30 mg/kg p.o.; nd = not determined1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Discovery and optimization of a novel class of orally active nonpeptidic endothelin-A receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (73)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's29 (39.73)18.2507
2000's35 (47.95)29.6817
2010's7 (9.59)24.3611
2020's2 (2.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.03

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 Index10.03 (24.57)
Research Supply Index4.30 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.03)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.74%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other71 (97.26%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]