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

C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O

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	15 / 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 8504	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 8504	15.0 nM [Ki]
PC-3 15 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8504	63.0 nM [IC50]
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8504	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 8504	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 8583	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 8583	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 8583	Ouabain Approved Use Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Unknown 2596

PubMed

Title	Date	PubMed
Ouabain-induced ventricular tachycardia and its effect on the performance and metabolism of the dog heart.	1959 Sep	13821777
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.	1968 Sep	19108278
Antiarrhythmic and antifibrillatory properties of aprindine.	1975 Aug	1151768
[Inhibitory effect of taurine on ouabain-induced arrythmia].	1975 Jan	125678
The effects of ketamine and of Innovar anesthesia on digitalis tolerance in dogs.	1975 Jan-Feb	1167743
[Glycogen content in rat brain in ouabain encephalopathy].	1975 Jan-Mar	1173001
[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects].	1990 Apr	1973400
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
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
Neuronal Fos-like immunoreactivity in ouabain-induced hypertension.	2000 Sep 8	10973588
Activation of Na+/K+-ATPase by the serum and glucocorticoid-dependent kinase isoforms.	2002	12590200
The renal-specific transporter mediates facilitative transport of organic anions at the brush border membrane of mouse renal tubules.	2004 Aug	15284287
Contribution of the endothelin and renin-angiotensin systems to the vascular changes in rats chronically treated with ouabain.	2004 Nov	15477225
[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
[Comparative study of properties of Na+, K+-ATPase and Mg2+-ATPase of the myometrium plasma membrane].	2005 Mar-Apr	16335235
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
ACTH-induced hypertension is dependent on the ouabain-binding site of the alpha2-Na+-K+-ATPase subunit.	2008 Jul	18487447
Chronic ouabain treatment increases the contribution of nitric oxide to endothelium-dependent relaxation.	2008 Jun	19043981
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
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 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 `Mon Mar 31 18:21:16 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:16 GMT 2025`
Record UNII	5ACL011P69
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OUABAIN

Common Name

English

G-STROPHANTHIN

Preferred 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

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