Page last updated: 2024-11-06

bms 180448

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

Description

BMS 180448: a potassium channel opener with cardioprotective and vasodilator properties; BMS-180426 is enantiomer with no antiischemic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122031
CHEMBL ID11802
MeSH IDM0224952
PubMed CID60880
CHEMBL ID44340
SCHEMBL ID4254900
SCHEMBL ID13970141
MeSH IDM0224952

Synonyms (22)

Synonym
bms 180448
trans-n-(4-chlorophenyl)-n'-cyano-n''-(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2h-1-benzopyran-4-yl)guanidine
guanidine, n-(4-chlorophenyl)-n'-cyano-n''-(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2h-1-benzopyran-4-yl)-, trans-
CHEMBL11802 ,
1-(4-chlorophenyl)-3-cyano-2-[(3r,4s)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine
144264-47-1
bdbm50409908
DTXSID90162661
AKOS040750825
bms-180448
CHEMBL44340
1-(4-chlorophenyl)-3-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine
144301-94-0
9b1i77ms94 ,
unii-9b1i77ms94
guanidine, n-(4-chlorophenyl)-n'-cyano-n''-(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2h-1-benzopyran-4-yl)-, (3s-trans)-
guanidine, n-(4-chlorophenyl)-n'-cyano-n''-((3s,4r)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2h-1-benzopyran-4-yl)-
SCHEMBL4254900
SCHEMBL13970141
Q27272290
DTXSID501107038
n-(4-chlorophenyl)-n'-cyano-n''-[(3s,4r)-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2h-1-benzopyran-4-yl]guanidine

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" With its good oral bioavailability (47%) and plasma elimination half-life (3 h) in rats, compound 3 offers an excellent candidate to investigate the role of residual vasorelaxant potency of 2 toward its cardioprotective activity in vivo."( Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity.
Ahmed, SZ; Atwal, KS; Baird, AJ; Ding, CZ; Dzwonczyk, S; Ferrara, FN; Grover, GJ; Humphreys, WG; McLaughlin, LG; Normandin, DE; Rovnyak, GC; Santafianos, D; Sleph, PG; Traeger, SC, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATP synthase subunit beta, mitochondrialBos taurus (cattle)IC50 (µMol)100.00000.48000.48000.4800AID68758
ATP synthase subunit delta, mitochondrialBos taurus (cattle)IC50 (µMol)100.00000.48000.48000.4800AID68758
ATP synthase subunit gamma, mitochondrialBos taurus (cattle)IC50 (µMol)100.00000.48000.48000.4800AID68758
ATP synthase subunit epsilon, mitochondrialBos taurus (cattle)IC50 (µMol)100.00000.48000.48000.4800AID68758
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)IC50 (µMol)100.00000.00031.38338.4000AID68758
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
proton transmembrane transportATP synthase subunit beta, mitochondrialBos taurus (cattle)
proton transmembrane transportATP synthase subunit delta, mitochondrialBos taurus (cattle)
aerobic respirationATP synthase subunit delta, mitochondrialBos taurus (cattle)
mitochondrial proton-transporting ATP synthase complex assemblyATP synthase subunit delta, mitochondrialBos taurus (cattle)
proton transmembrane transportATP synthase subunit gamma, mitochondrialBos taurus (cattle)
proton transmembrane transportATP synthase subunit epsilon, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingATP synthase subunit beta, mitochondrialBos taurus (cattle)
ATP bindingATP synthase subunit beta, mitochondrialBos taurus (cattle)
ATP hydrolysis activityATP synthase subunit beta, mitochondrialBos taurus (cattle)
proton-transporting ATPase activity, rotational mechanismATP synthase subunit beta, mitochondrialBos taurus (cattle)
proton transmembrane transporter activityATP synthase subunit delta, mitochondrialBos taurus (cattle)
protein bindingATP synthase subunit gamma, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
mitochondrial proton-transporting ATP synthase complexATP synthase subunit beta, mitochondrialBos taurus (cattle)
mitochondrial envelopeATP synthase subunit delta, mitochondrialBos taurus (cattle)
mitochondrial proton-transporting ATP synthase complexATP synthase subunit delta, mitochondrialBos taurus (cattle)
proton-transporting ATP synthase complexATP synthase subunit delta, mitochondrialBos taurus (cattle)
mitochondrial proton-transporting ATP synthase complexATP synthase subunit gamma, mitochondrialBos taurus (cattle)
mitochondrial proton-transporting ATP synthase complex, catalytic sector F(1)ATP synthase subunit epsilon, mitochondrialBos taurus (cattle)
mitochondrial proton-transporting ATP synthase complexATP synthase subunit epsilon, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID68762Inhibitory concentration towards rat mitochondrial F1F0-ATP synthase using a hexokinase / glucose-6-phosphate dehydrogenase coupled assay2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Small molecule mitochondrial F1F0 ATPase hydrolase inhibitors as cardioprotective agents. Identification of 4-(N-arylimidazole)-substituted benzopyran derivatives as selective hydrolase inhibitors.
AID68758Inhibitory concentration towards rat mitochondrial F1F0 ATP hydrolase using a pyruvate kinase / lactate dehydrogenase system2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Small molecule mitochondrial F1F0 ATPase hydrolase inhibitors as cardioprotective agents. Identification of 4-(N-arylimidazole)-substituted benzopyran derivatives as selective hydrolase inhibitors.
AID26495Oral bioavailability in rat1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Cardioselective anti-ischemic ATP-sensitive potassium channel openers.
AID179482Ratio of myocardial infarct zone to area at risk (IZ/AAR) in ischemic myocardium damage rat model (Cardioprotective effect) at 0.1 mg/Kg2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
A novel anti-ischemic ATP-sensitive potassium channel (K(ATP)) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N'-benzyl-N' '-cyanoguanidine analogue.
AID29422Plasma half-life was determined in rats1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Cardioselective anti-ischemic ATP-sensitive potassium channel openers.
AID196894Antiischemic potency is determined by EC25 value for increase in time to the onset of contracture in globally ischemic isolated perfused rat hearts.1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity.
AID195194Inhibition of methoxamine-contracted rat aorta (Vasorelaxant potency)2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
A novel anti-ischemic ATP-sensitive potassium channel (K(ATP)) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N'-benzyl-N' '-cyanoguanidine analogue.
AID68764Inhibitory concentration towards rat mitochondrial F1F0-ATP synthase using a pyruvate kinase / lactate dehydrogenase system2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Small molecule mitochondrial F1F0 ATPase hydrolase inhibitors as cardioprotective agents. Identification of 4-(N-arylimidazole)-substituted benzopyran derivatives as selective hydrolase inhibitors.
AID195202Tested for the vasorelaxant potency in methoxamine contracted rat aorta1995Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17
Cardioselective anti-ischemic ATP-sensitive potassium channel openers. 3. Structure-activity studies on benzopyranyl cyanoguanidines: modification of the cyanoguanidine portion.
AID233947Ratio of Antiischemic potency to vasorelaxant potency.1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Cardioselective antiischemic ATP-sensitive potassium channel (K(ATP)) openers. 6. Effect of modifications at C6 of benzopyranyl cyanoguanidines.
AID175289Anti-ischemic potency determined as concentration required for increase in time to contracture in globally ischemic rat hearts1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Cardioselective anti-ischemic ATP-sensitive potassium channel openers.
AID68762Inhibitory concentration towards rat mitochondrial F1F0-ATP synthase using a hexokinase / glucose-6-phosphate dehydrogenase coupled assay2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Small molecule mitochondrial F1F0 ATPase hydrolase inhibitors as cardioprotective agents. Identification of 4-(N-arylimidazole)-substituted benzopyran derivatives as selective hydrolase inhibitors.
AID179484Ratio of myocardial infarct zone to area at risk (IZ/AAR) in ischemic myocardium damage rat model (Cardioprotective effect) at 1 mg/Kg2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
A novel anti-ischemic ATP-sensitive potassium channel (K(ATP)) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N'-benzyl-N' '-cyanoguanidine analogue.
AID179483Ratio of myocardial infarct zone to area at risk (IZ/AAR) in ischemic myocardium damage rat model (Cardioprotective effect) at 0.3 mg/Kg2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
A novel anti-ischemic ATP-sensitive potassium channel (K(ATP)) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N'-benzyl-N' '-cyanoguanidine analogue.
AID195203Vasorelaxant potency determined by measurement of IC50 value for relaxation of rat aorta precontracted with methoxamine1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity.
AID196895Concentration necessary for increase in time to contracture by 25% in the globally ischemic rat hearts1995Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17
Cardioselective anti-ischemic ATP-sensitive potassium channel openers. 3. Structure-activity studies on benzopyranyl cyanoguanidines: modification of the cyanoguanidine portion.
AID175320The effective concentration (EC25) was measured for anti-ischemic activity on perfused rat hearts2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Recent developments in the biology and medicinal chemistry of potassium channel modulators: update from a decade of progress.
AID180680Vasorelaxant potency determined by inhibition of methoxamine-contracted rat aorta1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Cardioselective anti-ischemic ATP-sensitive potassium channel openers.
AID233806Ratio of the EC25 value for time to contracture and IC50 value for vasorelaxant potency indicates selectivity in vitro for the ischemic myocardium.1997Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1
Cardioselective antiischemic ATP-sensitive potassium channel (KATP) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity.
AID230962Ratio of the concentration increasing time to contracture by 25% (EC25) in rat heart and concentration showing vasorelaxant potency (IC50) in rat aorta.1995Journal of medicinal chemistry, Aug-18, Volume: 38, Issue:17
Cardioselective anti-ischemic ATP-sensitive potassium channel openers. 3. Structure-activity studies on benzopyranyl cyanoguanidines: modification of the cyanoguanidine portion.
AID175292Antiischemic potency by measurement of increase in time to contracture in globally ischemic isolated perfused rat hearts1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Cardioselective antiischemic ATP-sensitive potassium channel (K(ATP)) openers. 6. Effect of modifications at C6 of benzopyranyl cyanoguanidines.
AID437030Cardioprotective effect in Langendorff perfused isolated rat hearts assessed as reduction in ischemic injury2009Bioorganic & medicinal chemistry, Aug-01, Volume: 17, Issue:15
Predictive models, based on classification algorithms, for compounds potentially active as mitochondrial ATP-sensitive potassium channel openers.
AID195592Reduction rate of LDH release from rat neuronal cells injured by iron at 30 uM2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
A novel anti-ischemic ATP-sensitive potassium channel (K(ATP)) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N'-benzyl-N' '-cyanoguanidine analogue.
AID232312EC25 and IC50 Ratio of the compound2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Recent developments in the biology and medicinal chemistry of potassium channel modulators: update from a decade of progress.
AID179478Ratio of myocardial infarct zone to area at risk (AAR/LV) in ischemic myocardium damage rat model (Cardioprotective effect) at 0.3 mg/Kg2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
A novel anti-ischemic ATP-sensitive potassium channel (K(ATP)) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N'-benzyl-N' '-cyanoguanidine analogue.
AID181703In vitro relaxation of rat aorta precontracted with methoxamine.1999Journal of medicinal chemistry, Sep-09, Volume: 42, Issue:18
Cardioselective antiischemic ATP-sensitive potassium channel (K(ATP)) openers. 6. Effect of modifications at C6 of benzopyranyl cyanoguanidines.
AID231462Ratio between EC25 and EC50 values was determined1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Cardioselective anti-ischemic ATP-sensitive potassium channel openers.
AID180673The inhibitory concentration (IC50) for vasorelaxation on rat aorta2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Recent developments in the biology and medicinal chemistry of potassium channel modulators: update from a decade of progress.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (35)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's22 (62.86)18.2507
2000's13 (37.14)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.16

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 Index12.16 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews4 (12.90%)6.00%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other27 (87.10%)84.16%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]