OUABAIN OCTAHYDRATE

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
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

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium/potassium-transporting ATPase subunit alpha-2 4 Target ID: P50993 Gene ID: 477.0 Gene Symbol: ATP1A2 Target Organism: Homo sapiens (Human) Sources: http://www.selleckchem.com/products/ouabain.html	Inhibitor 8146	41.0 nM [Ki]
Sodium/potassium-transporting ATPase subunit alpha-3 4 Target ID: P13637 Gene ID: 478.0 Gene Symbol: ATP1A3 Target Organism: Homo sapiens (Human) Sources: http://www.selleckchem.com/products/ouabain.html	Inhibitor 8146	15.0 nM [Ki]
PC-3 13 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8146	63.0 nM [IC50]
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8146	37.0 nM [IC50]
Sodium/potassium-transporting ATPase subunit alpha-1 16 Target ID: P05023\|\|\|Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB01092	Inhibitor 8146	50.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Atrial fibrillation 131 Sources: http://www.druginfosys.com/drug.aspx?drugcode=537&type=9	Primary	Approved 8307	Ouabain Approved Use Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Cardiac arrhythmia 19 Sources: http://www.druginfosys.com/drug.aspx?drugcode=537&type=9	Primary	Approved 8307	Ouabain Approved Use Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Atrial flutter 6 Sources: http://www.druginfosys.com/drug.aspx?drugcode=537&type=9	Primary	Approved 8307	Ouabain Approved Use Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Unknown 2554

PubMed

Title	Date	PubMed
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.	1968 Sep	19108278
Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects.	1977 Jul	17729
[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects].	1990 Apr	1973400
Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.	1990 Sep	1700207
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Identification and characterization of a ouabain-like compound from human plasma.	1991 Jul 15	1648735
Effect of BN 52256 and other mediator antagonists on ouabain-induced ventricular fibrillation in sensitized guinea-pigs and on ischemia-induced fibrillation in rats.	1992	1632298
[Renal sodium handling in ouabain-hypertensive rats].	2005 Aug	16178440
[Comparative study of properties of Na+, K+-ATPase and Mg2+-ATPase of the myometrium plasma membrane].	2005 Mar-Apr	16335235
[Comparative analysis of the cardiac glycosides action on the growth of the cardiac tissue explants].	2005 Nov	16408638
Sodium pump alpha2 subunits control myogenic tone and blood pressure in mice.	2005 Nov 15	16166162
Central and peripheral renin-angiotensin systems in ouabain-induced hypertension.	2006 Aug	16565308
Functional heterogeneity of the "transporter" of electrogenic ionic pump of the Lumbricus terrestris somatic myocyte membrane.	2006 Dec	17603680
Ouabain at pathological concentrations might induce damage in human vascular endothelial cells.	2006 Feb	16412265
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase.	2006 Jul	16624565
Alterations in structure and mechanics of resistance arteries from ouabain-induced hypertensive rats.	2006 Jul	16473962
[Ouabain-induced apoptosis of Jurkat cells correlates with activation of caspase-3 and regulation of Bcl-2 gene family].	2006 Oct	17096883
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats].	2006 Oct	17062336
[Contribution of endothelin and its receptors to ouabain-induced hypertension in rats].	2006 Sep	16982439
Ouabain-induced hypertension enhances left ventricular contractility in rats.	2006 Sep 13	16716361
Endogenous brain Na pumps, brain ouabain-like substance and the alpha2 isoform in salt-dependent hypertension.	2007 Dec	17980562
Proteomics analysis of the proliferative effect of low-dose ouabain on human endothelial cells.	2007 Feb	17268060
Involvement of endogenous ouabain-like compound in the cardiac hypertrophic process in vivo.	2007 Mar 13	17266992
Visual behavior of adult goldfish with regenerating retina.	2007 May-Jun	17592671
The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats.	2008 Aug	19043511
Ouabain treatment changes the role of endothelial factors in rat resistance arteries.	2008 Dec 14	18976649
Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes.	2008 Feb 2	18031729
ACTH-induced hypertension is dependent on the ouabain-binding site of the alpha2-Na+-K+-ATPase subunit.	2008 Jul	18487447
Chronic ouabain treatment enhances cardiac myosin ATPase activity in rats.	2008 Jul	18346177
Chronic ouabain treatment increases the contribution of nitric oxide to endothelium-dependent relaxation.	2008 Jun	19043981
Proteomics investigation of protein expression changes in ouabain induced apoptosis in human umbilical vein endothelial cells.	2008 Jun 1	18247327
Structural and functional characteristic of a model for deep-seated lacunar infarct in rats.	2008 Oct 15	18657834
Response of sodium pump to ouabain challenge in human glioblastoma cells in culture.	2009	19995221
Intracellular potassium stabilizes human ether-à-go-go-related gene channels for export from endoplasmic reticulum.	2009 Apr	19139152
Animal model of mania induced by ouabain: Evidence of oxidative stress in submitochondrial particles of the rat brain.	2009 Dec	19447152
Extracellular signal regulated kinase 5 mediates signals triggered by the novel tumor promoter palytoxin.	2009 Dec 1	19716839
Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats.	2009 Jan	19145772
Chronic ouabain treatment induces vasa recta endothelial dysfunction in the rat.	2009 Jan	18945826
Digoxin and ouabain induce P-glycoprotein by activating calmodulin kinase II and hypoxia-inducible factor-1alpha in human colon cancer cells.	2009 Nov 1	19647009
The antiarrhythmic effect and possible ionic mechanisms of pilocarpine on animal models.	2009 Sep	19721134
Low-dose ouabain constricts small arteries from ouabain-hypertensive rats: implications for sustained elevation of vascular resistance.	2009 Sep	19617413
The new targets of ouabain in retinal interneurons of Sprague-Dawley rats.	2010 Apr 5	20105455
Evaluation of brain creatine kinase activity in an animal model of mania induced by ouabain.	2010 Feb	19911114
DNA damage after intracerebroventricular injection of ouabain in rats.	2010 Feb 26	20056132
Upregulation of Na+ and Ca2+ transporters in arterial smooth muscle from ouabain-induced hypertensive rats.	2010 Jan	19897708
Effects of long-term ouabain treatment on blood pressure, sodium excretion, and renal dopamine D(1) receptor levels in rats.	2010 Jan	19626329
Sodium-hydrogen exchange inhibition attenuates glycoside-induced hypertrophy in rat ventricular myocytes.	2010 Jan 1	19687166
Na+-dependent SR Ca2+ overload induces arrhythmogenic events in mouse cardiomyocytes with a human CPVT mutation.	2010 Jul 1	20080988
Effects of mood stabilizers on hippocampus and amygdala BDNF levels in an animal model of mania induced by ouabain.	2010 Jun	19954800
Dopamine-mediated inhibition of renal Na+/K+-ATPase in HK-2 cells is reduced by ouabain.	2010 May	20132239

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Sat Dec 17 01:13:09 UTC 2022` Edited by `admin` on `Sat Dec 17 01:13:09 UTC 2022`
Record UNII	1K0J875G48
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OUABAIN OCTAHYDRATE

Common Name

English

NSC-757425

Code

English

STROPHOPERM

Brand Name

English

CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXY-, OCTAHYDRATE, (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-

Common Name

English

ACOCANTHERIN OCTAHYDRATE

Common Name

English

STRODIVAL

Brand Name

English

PUROSTROPHAN

Brand Name

English

Code System Code Type Description

EPA CompTox

DTXSID7040730