Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H44O12.8H2O |
Molecular Weight | 728.7747 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.O.O.O.[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=TYBARJRCFHUHSN-DMJRSANLSA-N
InChI=1S/C29H44O12.8H2O/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;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1
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. |
|||
Primary | Ouabain Approved UseOuabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias. |
|||
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 effect of diphenylhydantoin sodium (dilantin), procaine hydrochloride, procaine amide hydrochloride, and quinidine hydrochloride upon ouabain-induced ventricular tachycardia in unanesthetized dogs. | 1954 Jul |
|
Antiarrhythmic and antifibrillatory properties of aprindine. | 1975 Aug |
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[Inhibitory effect of taurine on ouabain-induced arrythmia]. | 1975 Jan |
|
Effect of hypomagnesemia on ouabain-induced cardiac arrhythmias in dogs. | 1975 Jul |
|
Antiarrhythmic and hemodynamic effects of an aminosteroid (Org 3001) in the digitalized dog. | 1976 Mar |
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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 |
|
Effects of AH-1058, a new antiarrhythmic drug, on experimental arrhythmias and cardiac membrane currents. | 1999 Apr |
|
Synaptic plasticity in sympathetic ganglia from acquired and inherited forms of ouabain-dependent hypertension. | 2001 Aug |
|
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity. | 2001 Sep 1 |
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Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. | 2002 Apr |
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Alterations in phenylephrine-induced contractions and the vascular expression of Na+,K+-ATPase in ouabain-induced hypertension. | 2002 Feb |
|
Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors. | 2002 Nov |
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Tumour-specific activation of the sodium/iodide symporter gene under control of the glucose transporter gene 1 promoter (GTI-1.3). | 2003 May |
|
Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. | 2004 Mar |
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Biotin uptake by human proximal tubular epithelial cells: cellular and molecular aspects. | 2005 Apr |
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[Comparative study of properties of Na+, K+-ATPase and Mg2+-ATPase of the myometrium plasma membrane]. | 2005 Mar-Apr |
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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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Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase. | 2006 Jul |
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[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 |
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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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Visual behavior of adult goldfish with regenerating retina. | 2007 May-Jun |
|
Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes. | 2008 Feb 2 |
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Proteomics investigation of protein expression changes in ouabain induced apoptosis in human umbilical vein endothelial cells. | 2008 Jun 1 |
|
Response of sodium pump to ouabain challenge in human glioblastoma cells in culture. | 2009 |
|
DNA damage after intracerebroventricular injection of ouabain in rats. | 2010 Feb 26 |
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.
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD