OUABAIN

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

Structure Search

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

HIDE SMILES / InChI

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 8228	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 8228	15.0 nM [Ki]
PC-3 15 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8228	63.0 nM [IC50]
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8228	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 8228	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 8360	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 8360	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 8360	Ouabain Approved Use Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Unknown 2565

PubMed

Title	Date	PubMed
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.	1968 Sep	19108278
[Pharmacology of acebutolol in animals].	1975 Dec 31	1219628
[Inhibitory effect of taurine on ouabain-induced arrythmia].	1975 Jan	125678
Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects.	1977 Jul	17729
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Brain renin-angiotensin system and ouabain-induced sympathetic hyperactivity and hypertension in Wistar rats.	1999 Jul	10406832
Different effects of in vivo ouabain and digoxin on renal artery function and blood pressure in the rat.	2000 Sep	11016823
The cardiac sodium pump: structure and function.	2002	12479229
Delta-Aminolevulinic acid transport in murine mammary adenocarcinoma cells is mediated by beta transporters.	2002 Aug 12	12177786
Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors.	2002 Nov	12384489
11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications.	2003 Apr	12763919
The renal-specific transporter mediates facilitative transport of organic anions at the brush border membrane of mouse renal tubules.	2004 Aug	15284287
Neurogenic nitric oxide release increases in mesenteric arteries from ouabain hypertensive rats.	2004 May	15097235
Contribution of the endothelin and renin-angiotensin systems to the vascular changes in rats chronically treated with ouabain.	2004 Nov	15477225
Ouabain-induced hypertension alters the participation of endothelial factors in alpha-adrenergic responses differently in rat resistance and conductance mesenteric arteries.	2004 Sep	15302685
[Renal sodium handling in ouabain-hypertensive rats].	2005 Aug	16178440
The alpha2-isoform of Na-K-ATPase mediates ouabain-induced hypertension in mice and increased vascular contractility in vitro.	2005 Feb	15458945
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
Alterations in structure and mechanics of resistance arteries from ouabain-induced hypertensive rats.	2006 Jul	16473962
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats].	2006 Oct	17062336
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
Visual behavior of adult goldfish with regenerating retina.	2007 May-Jun	17592671
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
Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats.	2009 Jan	19145772
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
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
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
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 `Wed Jul 05 23:38:56 UTC 2023` Edited by `admin` on `Wed Jul 05 23:38:56 UTC 2023`
Record UNII	5ACL011P69
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OUABAIN

Common Name

English

Ouabain [WHO-DD]

Common Name

English

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

Common Name

English

NSC-25485

Code

English

G-STROPHANTHIN [MI]

Common Name

English

OUABAIN ANHYDROUS [HSDB]

Common Name

English

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

Common Name

English

G-STROPHANTHIN

Common Name

English

ACOCANTHERIN

Common Name

English

OUABAIN [MI]

Common Name

English

OUABAIN [EP MONOGRAPH]

Common Name

English

STROPHANTIN-G

Common Name

English

OUABAIN [MART.]

Common Name

English

GRATUS STROPHANTHIN

Common Name

English

G-STROPHANTHIN [JAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01AC01