Page last updated: 2024-11-11

bay 58-2667

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

Description

BAY 58-2667: activates guanylyl cyclase; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cinaciguat : A benzoic acid that is 4-(aminomethyl)benzoic acid in which the amino group is substituted by 4-carboxybutyl and 2-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)ethyl groups. It is a soluble guanylate cyclase activator, used for the treatment of acute decompensated heart failure. [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 CID9808022
CHEMBL ID1236936
CHEBI ID142433
SCHEMBL ID249267
MeSH IDM0459128

Synonyms (39)

Synonym
z90 ,
CHEMBL1236936
cinaciguat
bay-58-2667
329773-35-5
cinaciguat (jan/inn)
D07577
bay582667
cinaciguatum
CHEBI:142433
4-({(4-carboxybutyl)[2-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)ethyl]amino}methyl)benzoic acid
bay 58-2667
4-((4-carboxybutyl)(2-((4-phenethylbenzol)oxy)phenethyl)amino)methyl(benzoic)acid
cinaciguat [inn:jan]
59k0y58uad ,
unii-59k0y58uad
HY-14181
CS-1169
4-{[(4-carboxybutyl)[2-(2-{[4-(2-phenylethyl)phenyl]methoxy}phenyl)ethyl]amino]methyl}benzoic acid
gtpl5168
SCHEMBL249267
4-(((4-carboxybutyl)(2-(2-((4-(2-phenylethyl)phenyl)methoxy)phenyl)ethyl)amino)methyl)benzoic acid
cinaciguat [inn]
cinaciguat [jan]
cinaciguat [who-dd]
4-[[4-carboxybutyl-[2-[2-[[4-(2-phenylethyl)phenyl]methoxy]phenyl]ethyl]amino]methyl]benzoic acid
AKOS026750293
cinaciguat (bay 58-2667)
4-((4-carboxybutyl)(2-((4-phenethylbenzol)oxy) phenethyl) amino)methyl(benzoic) acid)
BCP07942
4-[n-(4-carboxybutyl)-n-[2-[2-[4-(2-phenylethyl)benzyloxy]phenyl]ethyl]aminomethyl]benzoic acid
Q5120172
4-(((4-carboxybutyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoic acid
NCGC00378941-05
D94958
DTXSID40954614
EX-A3260
AC-36368
4-(((4-carboxybutyl)(2-((4-phenethylbenzyl)oxy)phenethyl)amino)methyl)benzoicacid

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" No serious adverse events were reported."( Pharmacokinetics, pharmacodynamics, tolerability, and safety of the soluble guanylate cyclase activator cinaciguat (BAY 58-2667) in healthy male volunteers.
Artmeier-Brandt, U; Frey, R; Mück, W; Unger, S; Weimann, G; Wensing, G, 2008
)
0.56

Pharmacokinetics

ExcerptReferenceRelevance
" The aims of this study were to define the structural pharmacokinetic and pharmacodynamic models of cinaciguat in patients with ADHF, to characterize interindividual variability and to explore the effects of potential covariates."( Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure.
Frey, R; Mueck, W, 2010
)
0.36
" A 50% recovery to pharmacodynamic baseline values was estimated to occur within 1 hour and a complete return to baseline was estimated to occur within 3-4 hours after the end of infusion."( Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure.
Frey, R; Mueck, W, 2010
)
0.36
"Intravenously administered cinaciguat had predictable pharmacokinetic and haemodynamic effects in patients with ADHF."( Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure.
Frey, R; Mueck, W, 2010
)
0.36
" Pharmacokinetic variability tended to be somewhat increased in individuals with renal impairment."( Assessment of the effects of renal impairment on the pharmacokinetics of the soluble guanylate cyclase activator cinaciguat after a single intravenous dose.
Blunck, M; Frey, R; Lettieri, JT; Mazzu, AL; Mück, W; Scheerans, C; Sundaresan, PR, 2012
)
0.38
" An exploratory analysis of pharmacodynamic parameters was also conducted."( Pharmacokinetics of the soluble guanylate cyclase activator cinaciguat in individuals with hepatic impairment.
Blunck, M; Frey, R; Gnoth, MJ; Mück, W; Scheerans, C; Schmidt, A; Unger, S; Wensing, G, 2012
)
0.38

Bioavailability

ExcerptReferenceRelevance
" The NO/SGC/cGMP pathway is disrupted in patients with heart failure as a result of a decrease in NO bioavailability and an increase in NO-insensitive forms of sGC, resulting in insufficient vasodilation."( Cinaciguat, a soluble guanylate cyclase activator for the potential treatment of acute heart failure.
Caballero, R; Delpón, E; Duarte, J; Tamargo, J, 2010
)
0.36
" However, this pathway is disrupted in several cardiovascular diseases as a result of decreased NO bioavailability and increased NO-insensitive forms of sGC."( Effects of soluble guanylate cyclase activation on heart transplantation in a rat model.
Barnucz, E; Hirschberg, K; Karck, M; Korkmaz-Icöz, S; Li, S; Loganathan, S; Mikles, B; Radovits, T; Szabó, G, 2015
)
0.42
" Bay 58-2667 (cinaciguat) is able to re-activate defective sGC; however, the drug suffers from poor bioavailability and its systemic administration is linked to adverse events such as severe hypotension, which can hamper the therapeutic effect."( Targeted Delivery of Soluble Guanylate Cyclase (sGC) Activator Cinaciguat to Renal Mesangial Cells via Virus-Mimetic Nanoparticles Potentiates Anti-Fibrotic Effects by cGMP-Mediated Suppression of the TGF-β Pathway.
Fleischmann, D; Goepferich, A; Harloff, M; Maslanka Figueroa, S; Schlossmann, J, 2021
)
1.53
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
vasodilator agentA drug used to cause dilation of the blood vessels.
soluble guanylate cyclase activatorAny compound that binds to and activates soluble guanylate cyclase (EC 4.6.1.2).
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
[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 (4)

ClassDescription
benzoic acidsAny aromatic carboxylic acid that consists of benzene in which at least a single hydrogen has been substituted by a carboxy group.
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
dicarboxylic acidAny carboxylic acid containing two carboxy groups.
[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]

Pathways (5)

PathwayProteinsCompounds
Hemostasis23944
Platelet homeostasis1827
Nitric oxide stimulates guanylate cyclase313
Muscle contraction7721
Smooth Muscle Contraction2015

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1347411qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1469119Activation of soluble guanylate cyclase in human GTM3 cells assessed as increase in cGMP production after 30 mins by fluorescence assay relative to 1-{6-[5-chloro-2-({4-[trans-4-(trifluoromethyl)cyclohexyl]-benzyl}oxy)phenyl)pyridin-2-yl)-5-(trifluorometh2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
The Discovery of ( S)-1-(6-(3-((4-(1-(Cyclopropanecarbonyl)piperidin-4-yl)-2-methylphenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylic Acid, a Soluble Guanylate Cyclase Activator Specifically Designed for Topical Ocul
AID1469118Activation of soluble guanylate cyclase in human GTM3 cells assessed as increase in cGMP production after 30 mins by fluorescence assay2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
The Discovery of ( S)-1-(6-(3-((4-(1-(Cyclopropanecarbonyl)piperidin-4-yl)-2-methylphenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylic Acid, a Soluble Guanylate Cyclase Activator Specifically Designed for Topical Ocul
AID1066876Binding affinity to sGC subunit alpha-1/beta-1 catalytic domain (unknown origin) at 100 uM after 30 seconds by SPR analysis2014Bioorganic & medicinal chemistry letters, Feb-15, Volume: 24, Issue:4
Surface plasmon resonance using the catalytic domain of soluble guanylate cyclase allows the detection of enzyme activators.
AID1066877Binding affinity to full-length human recombinant sGC subunit alpha-1/beta-1 at 100 uM after 30 seconds by SPR analysis2014Bioorganic & medicinal chemistry letters, Feb-15, Volume: 24, Issue:4
Surface plasmon resonance using the catalytic domain of soluble guanylate cyclase allows the detection of enzyme activators.
AID1469117Activation of HUVEC-derived soluble guanylate cyclase expressed in CHOK1 cells assessed as increase in cGMP production after 1 hr by HTRF assay relative to 1-{6-[5-chloro-2-({4-[trans-4-(trifluoromethyl)cyclohexyl]-benzyl}oxy)phenyl)pyridin-2-yl)-5-(trifl2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
The Discovery of ( S)-1-(6-(3-((4-(1-(Cyclopropanecarbonyl)piperidin-4-yl)-2-methylphenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylic Acid, a Soluble Guanylate Cyclase Activator Specifically Designed for Topical Ocul
AID1469116Activation of HUVEC-derived soluble guanylate cyclase expressed in CHOK1 cells assessed as increase in cGMP production after 1 hr by HTRF assay2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
The Discovery of ( S)-1-(6-(3-((4-(1-(Cyclopropanecarbonyl)piperidin-4-yl)-2-methylphenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylic Acid, a Soluble Guanylate Cyclase Activator Specifically Designed for Topical Ocul
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (101)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's28 (27.72)29.6817
2010's60 (59.41)24.3611
2020's13 (12.87)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.67

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 Index17.67 (24.57)
Research Supply Index4.71 (2.92)
Research Growth Index4.75 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.67)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (5.77%)5.53%
Reviews16 (15.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other82 (78.85%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]