Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H44O12 |
Molecular Weight | 584.6525 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]6(O[C@H]1C[C@@H](O)[C@]2(CO)[C@@]3([H])[C@H](O)C[C@]4(C)[C@H](CC[C@]4(O)[C@]3([H])CC[C@]2(O)C1)C5=CC(=O)OC5)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O
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 | 584.6525 |
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
There is no available information about this compound
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 |
---|---|---|
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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[Inhibitory effect of taurine on ouabain-induced arrythmia]. | 1975 Jan |
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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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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
Brain renin-angiotensin system and ouabain-induced sympathetic hyperactivity and hypertension in Wistar rats. | 1999 Jul |
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Different effects of in vivo ouabain and digoxin on renal artery function and blood pressure in the rat. | 2000 Sep |
|
The cardiac sodium pump: structure and function. | 2002 |
|
Delta-Aminolevulinic acid transport in murine mammary adenocarcinoma cells is mediated by beta transporters. | 2002 Aug 12 |
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Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors. | 2002 Nov |
|
11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. | 2003 Apr |
|
The renal-specific transporter mediates facilitative transport of organic anions at the brush border membrane of mouse renal tubules. | 2004 Aug |
|
Neurogenic nitric oxide release increases in mesenteric arteries from ouabain hypertensive rats. | 2004 May |
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Contribution of the endothelin and renin-angiotensin systems to the vascular changes in rats chronically treated with ouabain. | 2004 Nov |
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Ouabain-induced hypertension alters the participation of endothelial factors in alpha-adrenergic responses differently in rat resistance and conductance mesenteric arteries. | 2004 Sep |
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[Renal sodium handling in ouabain-hypertensive rats]. | 2005 Aug |
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The alpha2-isoform of Na-K-ATPase mediates ouabain-induced hypertension in mice and increased vascular contractility in vitro. | 2005 Feb |
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Functional heterogeneity of the "transporter" of electrogenic ionic pump of the Lumbricus terrestris somatic myocyte membrane. | 2006 Dec |
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Ouabain at pathological concentrations might induce damage in human vascular endothelial cells. | 2006 Feb |
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Alterations in structure and mechanics of resistance arteries from ouabain-induced hypertensive rats. | 2006 Jul |
|
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats]. | 2006 Oct |
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Ouabain-induced hypertension enhances left ventricular contractility in rats. | 2006 Sep 13 |
|
Endogenous brain Na pumps, brain ouabain-like substance and the alpha2 isoform in salt-dependent hypertension. | 2007 Dec |
|
Visual behavior of adult goldfish with regenerating retina. | 2007 May-Jun |
|
Intracellular potassium stabilizes human ether-à-go-go-related gene channels for export from endoplasmic reticulum. | 2009 Apr |
|
Animal model of mania induced by ouabain: Evidence of oxidative stress in submitochondrial particles of the rat brain. | 2009 Dec |
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Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats. | 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 |
|
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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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 |
|
Na+-dependent SR Ca2+ overload induces arrhythmogenic events in mouse cardiomyocytes with a human CPVT mutation. | 2010 Jul 1 |
|
Dopamine-mediated inhibition of renal Na+/K+-ATPase in HK-2 cells is reduced by ouabain. | 2010 May |
Patents
Sample Use Guides
0.004 mg/kg - IV, as Recommended Initial dose
24 mg 24 hourly PO, as Maintenance dose
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.selleckchem.com/products/ouabain.html
Ouabain (0.1 uM-1.0 uM) inhibits the Na+ pump and increases stored Ca2+ in cultured rat astrocytes.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:38:56 UTC 2023
by
admin
on
Wed Jul 05 23:38:56 UTC 2023
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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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5ACL011P69
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3519
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CHEMBL222863
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7762
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OUABAIN
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DB01092
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M8270
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145798
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25485
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DTXSID0043765
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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 | |||
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SOLVATE->ANHYDROUS |
Related Record | Type | Details | ||
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ACTIVE MOIETY |