Details
Stereochemistry | ACHIRAL |
Molecular Formula | C36H39NO5 |
Molecular Weight | 565.6986 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCCCN(CCC1=C(OCC2=CC=C(CCC3=CC=CC=C3)C=C2)C=CC=C1)CC4=CC=C(C=C4)C(O)=O
InChI
InChIKey=WPYWMXNXEZFMAK-UHFFFAOYSA-N
InChI=1S/C36H39NO5/c38-35(39)12-6-7-24-37(26-30-19-21-33(22-20-30)36(40)41)25-23-32-10-4-5-11-34(32)42-27-31-17-15-29(16-18-31)14-13-28-8-2-1-3-9-28/h1-5,8-11,15-22H,6-7,12-14,23-27H2,(H,38,39)(H,40,41)
Molecular Formula | C36H39NO5 |
Molecular Weight | 565.6986 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Cinaciguat acts specifically on oxidized/haem-free soluble guanylyl cyclase by binding to the enzyme's haem pocket and mimicking the nitric-oxide-bound haem group. It is in clinical development for the treatment of acute decompensated heart failure. Cinaciguat had been in phase II clinical trials. However, trials were terminated early because of an excess of hypotension in the cinaciguat arms and subsequent slow enrolment.
Originator
Sources: http://adisinsight.springer.com/drugs/800021546
Curator's Comment: # Bayer HealthCare
Approval Year
PubMed
Title | Date | PubMed |
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NO- and haem-independent activation of soluble guanylyl cyclase: molecular basis and cardiovascular implications of a new pharmacological principle. | 2002 Jul |
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Residues stabilizing the heme moiety of the nitric oxide sensor soluble guanylate cyclase. | 2005 Apr 18 |
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Pharmacokinetics, pharmacodynamics, tolerability, and safety of the soluble guanylate cyclase activator cinaciguat (BAY 58-2667) in healthy male volunteers. | 2008 Dec |
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Gateways to clinical trials. | 2008 May |
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Cinaciguat, a soluble guanylate cyclase activator, causes potent and sustained pulmonary vasodilation in the ovine fetus. | 2009 Aug |
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Pharmacological activation of soluble guanylate cyclase protects the heart against ischemic injury. | 2009 Aug 25 |
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Role of guanylate cyclase modulators in decompensated heart failure. | 2009 Dec |
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Cinaciguat (BAY 58-2667) improves cardiopulmonary hemodynamics in patients with acute decompensated heart failure. | 2009 Jun 2 |
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Gateways to clinical trials. | 2009 Oct |
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Animal models related to congenital heart disease and clinical research in pulmonary hypertension. | 2010 |
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Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure. | 2010 |
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Direct fusion of subunits of heterodimeric nitric oxide sensitive guanylyl cyclase leads to functional enzymes with preserved biochemical properties: evidence for isoform specific activation by ciguates. | 2010 Dec 1 |
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Nitric oxide sensitive guanylyl cyclase activity decreases during cerebral postnatal development because of a reduction in heterodimerization. | 2010 Jan |
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Fluorescent fusion proteins of soluble guanylyl cyclase indicate proximity of the heme nitric oxide domain and catalytic domain. | 2010 Jul 15 |
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Structure of cinaciguat (BAY 58-2667) bound to Nostoc H-NOX domain reveals insights into heme-mimetic activation of the soluble guanylyl cyclase. | 2010 Jul 16 |
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Cinaciguat, a soluble guanylate cyclase activator for the potential treatment of acute heart failure. | 2010 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01067859
25 ug/h, 10 ug/h during 48 h
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19406872
Cinaciguat (1-50 nM) infused for 60 min starting 5 min before reperfusion significantly reduced infarction from 33.0 +/- 3.2% in control isolated rabbit hearts to 9.5-12.7% (P < 0.05).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:12:35 UTC 2023
by
admin
on
Fri Dec 15 16:12:35 UTC 2023
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Record UNII |
59K0Y58UAD
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C29707
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C87280
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C480588
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329773-35-5
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DTXSID40954614
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CINACIGUAT
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Related Record | Type | Details | ||
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TARGET -> ACTIVATOR |
Related Record | Type | Details | ||
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ACTIVE MOIETY |