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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H44O12
Molecular Weight 584.6536
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OUABAIN

SMILES

C[C@@]1([H])[C@@]([H])([C@]([H])([C@]([H])([C@@]([H])(O1)O[C@@]2([H])C[C@]([H])([C@]3(CO)[C@]4([H])[C@@]([H])(CC[C@@]3(C2)O)[C@]5(CC[C@]([H])(C6=CC(=O)OC6)[C@@]5(C)C[C@@]4([H])O)O)O)O)O)O

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 584.6536
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Ouabain was discovered and so named in 1888 by Amaud who isolated the crystalline glucoside from the bark and roots of the ouabaio tree, a species of Acocanthera used by the Somalis of East Africa as an arrow-poison. Ouabain, a cardiac glycoside similar to digitoxin, is used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation. Ouabain inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Ouabain is a selective Na+/K+, -ATPase inhibitor, binds to α2 /α3 subunit with Ki of 41 nM/15 nM. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Ouabain also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

CNS Activity

Curator's Comment:: SMALL doses of ouabain have powerful central nervous depressant effects. Ouabain directly stimulates the PNS center in the brain

Originator

Curator's Comment:: Ouabain was discovered and so named in 1888 by Amaud

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P50993
Gene ID: 477.0
Gene Symbol: ATP1A2
Target Organism: Homo sapiens (Human)
41.0 nM [Ki]
Target ID: P13637
Gene ID: 478.0
Gene Symbol: ATP1A3
Target Organism: Homo sapiens (Human)
15.0 nM [Ki]
63.0 nM [IC50]
37.0 nM [IC50]
Target ID: P05023|||Q9UJ20
Gene ID: 476.0
Gene Symbol: ATP1A1
Target Organism: Homo sapiens (Human)
50.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ouabain

Approved Use

Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Primary
Ouabain

Approved Use

Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Primary
Ouabain

Approved Use

Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
PubMed

PubMed

TitleDatePubMed
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.
1968 Sep
[Pharmacology of acebutolol in animals].
1975 Dec 31
Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects.
1977 Jul
[Pharmacological studies of celiprolol: III. Effects of celiprolol on the cardiovascular system and renal function, and its antiarrhythmic effects].
1990 Apr
Antiarrhythmic effects of optical isomers of cibenzoline on canine ventricular arrhythmias.
1990 Sep
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Ouabain-induced changes of calcium and potassium in slices of hippocampus of the rat: comparison to hypoxia and effect of R 56865.
1992 May
Brain renin-angiotensin system and ouabain-induced sympathetic hyperactivity and hypertension in Wistar rats.
1999 Jul
Regulation of tubular cell MCP-1 production by intracellular ions: a role for sodium and calcium.
2001
Structure-activity relationships for the hypertensinogenic activity of ouabain: role of the sugar and lactone ring.
2001 Feb
Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides.
2002 Apr
Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors.
2002 Nov
Effects of steroid hormones on (Na+, K+)-ATPase activity inhibition-induced amnesia on the step-through passive avoidance task in gonadectomized mice.
2004 Feb
Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump.
2004 Mar
Neurogenic nitric oxide release increases in mesenteric arteries from ouabain hypertensive rats.
2004 May
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase.
2006 Jul
[Ouabain-induced apoptosis of Jurkat cells correlates with activation of caspase-3 and regulation of Bcl-2 gene family].
2006 Oct
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats].
2006 Oct
[Contribution of endothelin and its receptors to ouabain-induced hypertension in rats].
2006 Sep
Ouabain-induced hypertension enhances left ventricular contractility in rats.
2006 Sep 13
Endogenous brain Na pumps, brain ouabain-like substance and the alpha2 isoform in salt-dependent hypertension.
2007 Dec
Involvement of endogenous ouabain-like compound in the cardiac hypertrophic process in vivo.
2007 Mar 13
The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats.
2008 Aug
Ouabain treatment changes the role of endothelial factors in rat resistance arteries.
2008 Dec 14
Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes.
2008 Feb 2
ACTH-induced hypertension is dependent on the ouabain-binding site of the alpha2-Na+-K+-ATPase subunit.
2008 Jul
Chronic ouabain treatment enhances cardiac myosin ATPase activity in rats.
2008 Jul
Chronic ouabain treatment increases the contribution of nitric oxide to endothelium-dependent relaxation.
2008 Jun
Proteomics investigation of protein expression changes in ouabain induced apoptosis in human umbilical vein endothelial cells.
2008 Jun 1
Structural and functional characteristic of a model for deep-seated lacunar infarct in rats.
2008 Oct 15
Response of sodium pump to ouabain challenge in human glioblastoma cells in culture.
2009
Intracellular potassium stabilizes human ether-à-go-go-related gene channels for export from endoplasmic reticulum.
2009 Apr
Animal model of mania induced by ouabain: Evidence of oxidative stress in submitochondrial particles of the rat brain.
2009 Dec
Extracellular signal regulated kinase 5 mediates signals triggered by the novel tumor promoter palytoxin.
2009 Dec 1
Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats.
2009 Jan
Chronic ouabain treatment induces vasa recta endothelial dysfunction in the rat.
2009 Jan
Digoxin and ouabain induce P-glycoprotein by activating calmodulin kinase II and hypoxia-inducible factor-1alpha in human colon cancer cells.
2009 Nov 1
The antiarrhythmic effect and possible ionic mechanisms of pilocarpine on animal models.
2009 Sep
Low-dose ouabain constricts small arteries from ouabain-hypertensive rats: implications for sustained elevation of vascular resistance.
2009 Sep
The new targets of ouabain in retinal interneurons of Sprague-Dawley rats.
2010 Apr 5
Evaluation of brain creatine kinase activity in an animal model of mania induced by ouabain.
2010 Feb
DNA damage after intracerebroventricular injection of ouabain in rats.
2010 Feb 26
Upregulation of Na+ and Ca2+ transporters in arterial smooth muscle from ouabain-induced hypertensive rats.
2010 Jan
Effects of long-term ouabain treatment on blood pressure, sodium excretion, and renal dopamine D(1) receptor levels in rats.
2010 Jan
Sodium-hydrogen exchange inhibition attenuates glycoside-induced hypertrophy in rat ventricular myocytes.
2010 Jan 1
Na+-dependent SR Ca2+ overload induces arrhythmogenic events in mouse cardiomyocytes with a human CPVT mutation.
2010 Jul 1
Effects of mood stabilizers on hippocampus and amygdala BDNF levels in an animal model of mania induced by ouabain.
2010 Jun
Dopamine-mediated inhibition of renal Na+/K+-ATPase in HK-2 cells is reduced by ouabain.
2010 May
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:09:57 UTC 2021
Edited
by admin
on Fri Jun 25 21:09:57 UTC 2021
Record UNII
5ACL011P69
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OUABAIN
EP   MART.   MI   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
JAN   MI  
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
OUABAIN [WHO-DD]
Common Name English
G-STROPHANTHIN [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC C01AC01
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
WHO-VATC QC01AC01
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
Code System Code Type Description
MESH
D010042
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-139-3
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
FDA UNII
5ACL011P69
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
HSDB
3519
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL222863
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
PUBCHEM
439501
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
DRUG CENTRAL
2004
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
IUPHAR
4826
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
EVMPD
SUB14721MIG
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
RXCUI
7762
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
OUABAIN
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
DRUG BANK
DB01092
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
MERCK INDEX
M8270
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY Merck Index
EPA CompTox
630-60-4
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
CAS
630-60-4
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY
MERCK INDEX
M10252
Created by admin on Fri Jun 25 21:09:57 UTC 2021 , Edited by admin on Fri Jun 25 21:09:57 UTC 2021
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY