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
Na+-dependent SR Ca2+ overload induces arrhythmogenic events in mouse cardiomyocytes with a human CPVT mutation.	2010-07-01	20080988
Effects of mood stabilizers on hippocampus and amygdala BDNF levels in an animal model of mania induced by ouabain.	2010-06	19954800
Dopamine-mediated inhibition of renal Na+/K+-ATPase in HK-2 cells is reduced by ouabain.	2010-05	20132239
The new targets of ouabain in retinal interneurons of Sprague-Dawley rats.	2010-04-05	20105455
DNA damage after intracerebroventricular injection of ouabain in rats.	2010-02-26	20056132
Evaluation of brain creatine kinase activity in an animal model of mania induced by ouabain.	2010-02	19911114
Sodium-hydrogen exchange inhibition attenuates glycoside-induced hypertrophy in rat ventricular myocytes.	2010-01-01	19687166
Upregulation of Na+ and Ca2+ transporters in arterial smooth muscle from ouabain-induced hypertensive rats.	2010-01	19897708
Effects of long-term ouabain treatment on blood pressure, sodium excretion, and renal dopamine D(1) receptor levels in rats.	2010-01	19626329
Extracellular signal regulated kinase 5 mediates signals triggered by the novel tumor promoter palytoxin.	2009-12-01	19716839
Animal model of mania induced by ouabain: Evidence of oxidative stress in submitochondrial particles of the rat brain.	2009-12	19447152
Digoxin and ouabain induce P-glycoprotein by activating calmodulin kinase II and hypoxia-inducible factor-1alpha in human colon cancer cells.	2009-11-01	19647009
The antiarrhythmic effect and possible ionic mechanisms of pilocarpine on animal models.	2009-09	19721134
Low-dose ouabain constricts small arteries from ouabain-hypertensive rats: implications for sustained elevation of vascular resistance.	2009-09	19617413
Intracellular potassium stabilizes human ether-à-go-go-related gene channels for export from endoplasmic reticulum.	2009-04	19139152
Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats.	2009-01	19145772
Chronic ouabain treatment induces vasa recta endothelial dysfunction in the rat.	2009-01	18945826
Response of sodium pump to ouabain challenge in human glioblastoma cells in culture.	2009	19995221
Ouabain treatment changes the role of endothelial factors in rat resistance arteries.	2008-12-14	18976649
Structural and functional characteristic of a model for deep-seated lacunar infarct in rats.	2008-10-15	18657834
The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats.	2008-08	19043511
ACTH-induced hypertension is dependent on the ouabain-binding site of the alpha2-Na+-K+-ATPase subunit.	2008-07	18487447
Chronic ouabain treatment enhances cardiac myosin ATPase activity in rats.	2008-07	18346177
Proteomics investigation of protein expression changes in ouabain induced apoptosis in human umbilical vein endothelial cells.	2008-06-01	18247327
Chronic ouabain treatment increases the contribution of nitric oxide to endothelium-dependent relaxation.	2008-06	19043981
Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes.	2008-02-02	18031729
Endogenous brain Na pumps, brain ouabain-like substance and the alpha2 isoform in salt-dependent hypertension.	2007-12	17980562
Involvement of endogenous ouabain-like compound in the cardiac hypertrophic process in vivo.	2007-03-13	17266992
Proteomics analysis of the proliferative effect of low-dose ouabain on human endothelial cells.	2007-02	17268060
Functional heterogeneity of the "transporter" of electrogenic ionic pump of the Lumbricus terrestris somatic myocyte membrane.	2006-12	17603680
[Ouabain-induced apoptosis of Jurkat cells correlates with activation of caspase-3 and regulation of Bcl-2 gene family].	2006-10	17096883
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats].	2006-10	17062336
Ouabain-induced hypertension enhances left ventricular contractility in rats.	2006-09-13	16716361
[Contribution of endothelin and its receptors to ouabain-induced hypertension in rats].	2006-09	16982439
Central and peripheral renin-angiotensin systems in ouabain-induced hypertension.	2006-08	16565308
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase.	2006-07	16624565
Alterations in structure and mechanics of resistance arteries from ouabain-induced hypertensive rats.	2006-07	16473962
Visual behavior of adult goldfish with regenerating retina.	2006-02-12	17592671
Ouabain at pathological concentrations might induce damage in human vascular endothelial cells.	2006-02	16412265
[Comparative study of properties of Na+, K+-ATPase and Mg2+-ATPase of the myometrium plasma membrane].	2005-12-13	16335235
Sodium pump alpha2 subunits control myogenic tone and blood pressure in mice.	2005-11-15	16166162
[Comparative analysis of the cardiac glycosides action on the growth of the cardiac tissue explants].	2005-11	16408638
[Renal sodium handling in ouabain-hypertensive rats].	2005-08	16178440
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
Identification and characterization of a ouabain-like compound from human plasma.	1991-07-15	1648735
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653
Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.	1990-09	1700207
[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects].	1990-04	1973400
Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects.	1977-07	17729
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.	1968-09	19108278

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

Download

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