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Cinaciguat

CAS No.:
329773-35-5
Catalog Number:
AG00C6F6
Molecular Formula:
C36H39NO5
Molecular Weight:
565.6986
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
2mg
99%
1 week
United States
$223
- +
5mg
99%
1 week
United States
$307
- +
10mg
99%
1 week
United States
$473
- +
50mg
99%
1 week
United States
$1557
- +
Product Description
Catalog Number:
AG00C6F6
Chemical Name:
Cinaciguat
CAS Number:
329773-35-5
Molecular Formula:
C36H39NO5
Molecular Weight:
565.6986
MDL Number:
MFCD18782678
IUPAC Name:
4-[[4-carboxybutyl-[2-[2-[[4-(2-phenylethyl)phenyl]methoxy]phenyl]ethyl]amino]methyl]benzoic acid
InChI:
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)
InChI Key:
WPYWMXNXEZFMAK-UHFFFAOYSA-N
SMILES:
OC(=O)CCCCN(Cc1ccc(cc1)C(=O)O)CCc1ccccc1OCc1ccc(cc1)CCc1ccccc1
UNII:
59K0Y58UAD
Properties
Complexity:
767  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
565.283g/mol
Formal Charge:
0
Heavy Atom Count:
42  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
565.71g/mol
Monoisotopic Mass:
565.283g/mol
Rotatable Bond Count:
17  
Topological Polar Surface Area:
87.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9  
Literature
Title Journal
Novel sGC Stimulators and sGC Activators for the Treatment of Heart Failure. Handbook of experimental pharmacology 20170101
Pharmacokinetics of the soluble guanylate cyclase activator cinaciguat in individuals with hepatic impairment. Journal of clinical pharmacology 20121101
Cinaciguat, a soluble guanylate cyclase activator: results from the randomized, controlled, phase IIb COMPOSE programme in acute heart failure syndromes. European journal of heart failure 20120901
Assessment of the effects of renal impairment on the pharmacokinetics of the soluble guanylate cyclase activator cinaciguat after a single intravenous dose. Journal of clinical pharmacology 20120801
Insight into the rescue of oxidized soluble guanylate cyclase by the activator cinaciguat. Chembiochem : a European journal of chemical biology 20120507
Cinaciguat, a novel activator of soluble guanylate cyclase, protects against ischemia/reperfusion injury: role of hydrogen sulfide. American journal of physiology. Heart and circulatory physiology 20120315
Cobinamides are novel coactivators of nitric oxide receptor that target soluble guanylyl cyclase catalytic domain. The Journal of pharmacology and experimental therapeutics 20120301
Stimulators and activators of soluble guanylate cyclase: review and potential therapeutic indications. Critical care research and practice 20120101
Cinaciguat, a soluble guanylate cyclase activator, augments cGMP after oxidative stress and causes pulmonary vasodilation in neonatal pulmonary hypertension. American journal of physiology. Lung cellular and molecular physiology 20111101
NOX1, 2, 4, 5: counting out oxidative stress. British journal of pharmacology 20111001
Measuring oxidative burden and predicting pharmacological response in coronary artery disease patients with a novel direct activator of haem-free/oxidised sGC. Atherosclerosis 20111001
New perspectives for the treatment of pulmonary hypertension. British journal of pharmacology 20110501
Soluble guanylate cyclase modulators in heart failure. Current heart failure reports 20110301
Pre-conditioning with the soluble guanylate cyclase activator Cinaciguat reduces ischaemia-reperfusion injury after cardiopulmonary bypass. European journal of cardio-thoracic surgery : official journal of the European Association for Cardio-thoracic Surgery 20110201
Soluble guanylate cyclase activation with cinaciguat: a new approach to the treatment of decompensated heart failure. Cardiology in review 20110101
Fluorescence dequenching makes haem-free soluble guanylate cyclase detectable in living cells. PloS one 20110101
The amino-terminus of nitric oxide sensitive guanylyl cyclase α₁ does not affect dimerization but influences subcellular localization. PloS one 20110101
Identification of residues in the heme domain of soluble guanylyl cyclase that are important for basal and stimulated catalytic activity. PloS one 20110101
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. Biochemical pharmacology 20101201
Cinaciguat, a soluble guanylate cyclase activator for the potential treatment of acute heart failure. Current opinion in investigational drugs (London, England : 2000) 20100901
Structure of cinaciguat (BAY 58-2667) bound to Nostoc H-NOX domain reveals insights into heme-mimetic activation of the soluble guanylyl cyclase. The Journal of biological chemistry 20100716
Nitric oxide sensitive guanylyl cyclase activity decreases during cerebral postnatal development because of a reduction in heterodimerization. Journal of neurochemistry 20100101
Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure. Clinical pharmacokinetics 20100101
Animal models related to congenital heart disease and clinical research in pulmonary hypertension. Cardiology 20100101
Fluorescent fusion proteins of soluble guanylyl cyclase indicate proximity of the heme nitric oxide domain and catalytic domain. PloS one 20100101
Anti-aggregating effect of BAY 58-2667, an activator of soluble guanylyl cyclase. Vascular pharmacology 20100101
Vasodilators in the treatment of acute heart failure: what we know, what we don't. Heart failure reviews 20091201
Role of guanylate cyclase modulators in decompensated heart failure. Heart failure reviews 20091201
Soluble guanylate cyclase agonists inhibit expression and procoagulant activity of tissue factor. Arteriosclerosis, thrombosis, and vascular biology 20091001
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20091001
Pharmacological activation of soluble guanylate cyclase protects the heart against ischemic injury. Circulation 20090825
Cinaciguat, a soluble guanylate cyclase activator, causes potent and sustained pulmonary vasodilation in the ovine fetus. American journal of physiology. Lung cellular and molecular physiology 20090801
Human trabecular meshwork cell volume decrease by NO-independent soluble guanylate cyclase activators YC-1 and BAY-58-2667 involves the BKCa ion channel. Investigative ophthalmology & visual science 20090701
BAY 58-2667, a nitric oxide-independent guanylyl cyclase activator, pharmacologically post-conditions rabbit and rat hearts. European heart journal 20090701
Distinct molecular requirements for activation or stabilization of soluble guanylyl cyclase upon haem oxidation-induced degradation. British journal of pharmacology 20090701
Soluble guanylate cyclase: not a dull enzyme. Circulation 20090602
Cinaciguat (BAY 58-2667) improves cardiopulmonary hemodynamics in patients with acute decompensated heart failure. Circulation 20090602
NO- and haem-independent soluble guanylate cyclase activators. Handbook of experimental pharmacology 20090101
Pharmacokinetics, pharmacodynamics, tolerability, and safety of the soluble guanylate cyclase activator cinaciguat (BAY 58-2667) in healthy male volunteers. Journal of clinical pharmacology 20081201
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20080501
Probing the presence of the ligand-binding haem in cellular nitric oxide receptors. British journal of pharmacology 20080401
Inhaled agonists of soluble guanylate cyclase induce selective pulmonary vasodilation. American journal of respiratory and critical care medicine 20071201
Inhibition of TGF-beta induced lung fibroblast to myofibroblast conversion by phosphodiesterase inhibiting drugs and activators of soluble guanylyl cyclase. European journal of pharmacology 20071015
Targeting heme-oxidized soluble guanylate cyclase: solution for all cardiorenal problems in heart failure? Hypertension (Dallas, Tex. : 1979) 20070501
Targeting heme-oxidized soluble guanylate cyclase in experimental heart failure. Hypertension (Dallas, Tex. : 1979) 20070501
Nitric oxide-independent stimulation of soluble guanylate cyclase with BAY 41-2272 in cardiovascular disease. Cardiovascular drug reviews 20070101
Deconstructing endothelial dysfunction: soluble guanylyl cyclase oxidation and the NO resistance syndrome. The Journal of clinical investigation 20060901
Targeting the heme-oxidized nitric oxide receptor for selective vasodilatation of diseased blood vessels. The Journal of clinical investigation 20060901
NO-independent activation of soluble guanylate cyclase prevents disease progression in rats with 5/6 nephrectomy. British journal of pharmacology 20060701
Activation of soluble guanylate cyclase reverses experimental pulmonary hypertension and vascular remodeling. Circulation 20060117
Characterization of the first potent and selective PDE9 inhibitor using a cGMP reporter cell line. Molecular pharmacology 20051201
Clinical potential of nitric oxide-independent soluble guanylate cyclase activators. Current opinion in investigational drugs (London, England : 2000) 20050901
Residues stabilizing the heme moiety of the nitric oxide sensor soluble guanylate cyclase. European journal of pharmacology 20050418
A cell-based cGMP assay useful for ultra-high-throughput screening and identification of modulators of the nitric oxide/cGMP pathway. Analytical biochemistry 20050401
Preparation of heme-free soluble guanylate cyclase. Protein expression and purification 20030901
Mechanisms of nitric oxide independent activation of soluble guanylyl cyclase. European journal of pharmacology 20030516
NO- and haem-independent activation of soluble guanylyl cyclase: molecular basis and cardiovascular implications of a new pharmacological principle. British journal of pharmacology 20020701
Properties