Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H44O12 |
Molecular Weight | 584.6536 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@@]([H])(O1)O[C@@]2([H])C[C@]([H])([C@]3(CO)[C@]4([H])[C@@]([H])(CC[C@@]3(C2)O)[C@]5(CC[C@]([H])(C6=CC(=O)OC6)[C@@]5(C)C[C@@]4([H])O)O)O)O)O)O
InChI
InChIKey=LPMXVESGRSUGHW-HBYQJFLCSA-N
InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
Molecular Formula | C29H44O12 |
Molecular Weight | 584.6536 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 14 / 15 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugbank.ca/drugs/DB01092Curator's Comment:: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23761677
http://www.druginfosys.com/drug.aspx?drugcode=537&type=9
Sources: https://www.drugbank.ca/drugs/DB01092
Curator's Comment:: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23761677
http://www.druginfosys.com/drug.aspx?drugcode=537&type=9
Ouabain was discovered and so named in 1888 by Amaud who isolated the crystalline glucoside from the bark and roots of the ouabaio tree, a species of Acocanthera used by the Somalis of East Africa as an arrow-poison. Ouabain, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation. Ouabain inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Ouabain is a selective Na+/K+, -ATPase inhibitor, binds to α2 /α3 subunit with Ki of 41 nM/15 nM. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Ouabain also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
Originator
Sources: http://www.jbc.org/content/96/3/647.full.pdf
Curator's Comment:: Ouabain was discovered and so named in 1888 by Amaud
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P50993 Gene ID: 477.0 Gene Symbol: ATP1A2 Target Organism: Homo sapiens (Human) Sources: http://www.selleckchem.com/products/ouabain.html |
41.0 nM [Ki] | ||
Target ID: P13637 Gene ID: 478.0 Gene Symbol: ATP1A3 Target Organism: Homo sapiens (Human) Sources: http://www.selleckchem.com/products/ouabain.html |
15.0 nM [Ki] | ||
Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895 |
63.0 nM [IC50] | ||
Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895 |
37.0 nM [IC50] | ||
Target ID: P05023|||Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB01092 |
50.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Ouabain Approved UseOuabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias. |
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Primary | Ouabain Approved UseOuabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias. |
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Primary | Ouabain Approved UseOuabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias. |
|||
PubMed
Title | Date | PubMed |
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The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias. | 1968 Sep |
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[Pharmacology of acebutolol in animals]. | 1975 Dec 31 |
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Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects. | 1977 Jul |
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[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects]. | 1990 Apr |
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Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias. | 1990 Sep |
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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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Ouabain-induced changes of calcium and potassium in slices of hippocampus of the rat: comparison to hypoxia and effect of R 56865. | 1992 May |
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Brain renin-angiotensin system and ouabain-induced sympathetic hyperactivity and hypertension in Wistar rats. | 1999 Jul |
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Regulation of tubular cell MCP-1 production by intracellular ions: a role for sodium and calcium. | 2001 |
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Structure-activity relationships for the hypertensinogenic activity of ouabain: role of the sugar and lactone ring. | 2001 Feb |
|
Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. | 2002 Apr |
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Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors. | 2002 Nov |
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Effects of steroid hormones on (Na+, K+)-ATPase activity inhibition-induced amnesia on the step-through passive avoidance task in gonadectomized mice. | 2004 Feb |
|
Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. | 2004 Mar |
|
Neurogenic nitric oxide release increases in mesenteric arteries from ouabain hypertensive rats. | 2004 May |
|
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase. | 2006 Jul |
|
[Ouabain-induced apoptosis of Jurkat cells correlates with activation of caspase-3 and regulation of Bcl-2 gene family]. | 2006 Oct |
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[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats]. | 2006 Oct |
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[Contribution of endothelin and its receptors to ouabain-induced hypertension in rats]. | 2006 Sep |
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Ouabain-induced hypertension enhances left ventricular contractility in rats. | 2006 Sep 13 |
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Endogenous brain Na pumps, brain ouabain-like substance and the alpha2 isoform in salt-dependent hypertension. | 2007 Dec |
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Involvement of endogenous ouabain-like compound in the cardiac hypertrophic process in vivo. | 2007 Mar 13 |
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The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats. | 2008 Aug |
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Ouabain treatment changes the role of endothelial factors in rat resistance arteries. | 2008 Dec 14 |
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Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes. | 2008 Feb 2 |
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ACTH-induced hypertension is dependent on the ouabain-binding site of the alpha2-Na+-K+-ATPase subunit. | 2008 Jul |
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Chronic ouabain treatment enhances cardiac myosin ATPase activity in rats. | 2008 Jul |
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Chronic ouabain treatment increases the contribution of nitric oxide to endothelium-dependent relaxation. | 2008 Jun |
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Proteomics investigation of protein expression changes in ouabain induced apoptosis in human umbilical vein endothelial cells. | 2008 Jun 1 |
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Structural and functional characteristic of a model for deep-seated lacunar infarct in rats. | 2008 Oct 15 |
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Response of sodium pump to ouabain challenge in human glioblastoma cells in culture. | 2009 |
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Intracellular potassium stabilizes human ether-à-go-go-related gene channels for export from endoplasmic reticulum. | 2009 Apr |
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Animal model of mania induced by ouabain: Evidence of oxidative stress in submitochondrial particles of the rat brain. | 2009 Dec |
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Extracellular signal regulated kinase 5 mediates signals triggered by the novel tumor promoter palytoxin. | 2009 Dec 1 |
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Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats. | 2009 Jan |
|
Chronic ouabain treatment induces vasa recta endothelial dysfunction in the rat. | 2009 Jan |
|
Digoxin and ouabain induce P-glycoprotein by activating calmodulin kinase II and hypoxia-inducible factor-1alpha in human colon cancer cells. | 2009 Nov 1 |
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The antiarrhythmic effect and possible ionic mechanisms of pilocarpine on animal models. | 2009 Sep |
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Low-dose ouabain constricts small arteries from ouabain-hypertensive rats: implications for sustained elevation of vascular resistance. | 2009 Sep |
|
The new targets of ouabain in retinal interneurons of Sprague-Dawley rats. | 2010 Apr 5 |
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Evaluation of brain creatine kinase activity in an animal model of mania induced by ouabain. | 2010 Feb |
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DNA damage after intracerebroventricular injection of ouabain in rats. | 2010 Feb 26 |
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Upregulation of Na+ and Ca2+ transporters in arterial smooth muscle from ouabain-induced hypertensive rats. | 2010 Jan |
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Effects of long-term ouabain treatment on blood pressure, sodium excretion, and renal dopamine D(1) receptor levels in rats. | 2010 Jan |
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Sodium-hydrogen exchange inhibition attenuates glycoside-induced hypertrophy in rat ventricular myocytes. | 2010 Jan 1 |
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Na+-dependent SR Ca2+ overload induces arrhythmogenic events in mouse cardiomyocytes with a human CPVT mutation. | 2010 Jul 1 |
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Effects of mood stabilizers on hippocampus and amygdala BDNF levels in an animal model of mania induced by ouabain. | 2010 Jun |
|
Dopamine-mediated inhibition of renal Na+/K+-ATPase in HK-2 cells is reduced by ouabain. | 2010 May |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:09:57 UTC 2021
by
admin
on
Fri Jun 25 21:09:57 UTC 2021
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Record UNII |
5ACL011P69
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
C01AC01
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QC01AC01
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D010042
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211-139-3
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5ACL011P69
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3519
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CHEMBL222863
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439501
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2004
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4826
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SUB14721MIG
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7762
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PRIMARY | RxNorm | ||
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OUABAIN
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DB01092
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M8270
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630-60-4
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630-60-4
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M10252
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |