U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of OUABAIN

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
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

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
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
Identification and characterization of a ouabain-like compound from human plasma.
1991 Jul 15
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
[Renal sodium handling in ouabain-hypertensive rats].
2005 Aug
[Comparative study of properties of Na+, K+-ATPase and Mg2+-ATPase of the myometrium plasma membrane].
2005 Mar-Apr
[Comparative analysis of the cardiac glycosides action on the growth of the cardiac tissue explants].
2005 Nov
Sodium pump alpha2 subunits control myogenic tone and blood pressure in mice.
2005 Nov 15
Central and peripheral renin-angiotensin systems in ouabain-induced hypertension.
2006 Aug
Functional heterogeneity of the "transporter" of electrogenic ionic pump of the Lumbricus terrestris somatic myocyte membrane.
2006 Dec
Ouabain at pathological concentrations might induce damage in human vascular endothelial cells.
2006 Feb
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase.
2006 Jul
Alterations in structure and mechanics of resistance arteries from ouabain-induced hypertensive rats.
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
Proteomics analysis of the proliferative effect of low-dose ouabain on human endothelial cells.
2007 Feb
Involvement of endogenous ouabain-like compound in the cardiac hypertrophic process in vivo.
2007 Mar 13
Visual behavior of adult goldfish with regenerating retina.
2007 May-Jun
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

0.004 mg/kg - IV, as Recommended Initial dose 24 mg 24 hourly PO, as Maintenance dose
Route of Administration: Other
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 Fri Dec 15 16:11:22 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:22 GMT 2023
Record UNII
5ACL011P69
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OUABAIN
EP   MART.   MI   WHO-DD  
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
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
G-STROPHANTHIN [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC C01AC01
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
WHO-VATC QC01AC01
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
Code System Code Type Description
MESH
D010042
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
CHEBI
472805
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-139-3
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
SMS_ID
100000076204
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
FDA UNII
5ACL011P69
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
HSDB
3519
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL222863
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
PUBCHEM
439501
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
DRUG CENTRAL
2004
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
IUPHAR
4826
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
EVMPD
SUB14721MIG
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
RXCUI
7762
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
OUABAIN
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
DRUG BANK
DB01092
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
MERCK INDEX
m8270
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY Merck Index
CHEBI
145798
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
NSC
25485
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID0043765
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
CAS
630-60-4
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY
MERCK INDEX
m10252
Created by admin on Fri Dec 15 16:11:23 GMT 2023 , Edited by admin on Fri Dec 15 16:11:23 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY