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
[Pharmacology of acebutolol in animals].
1975 Dec 31
[Inhibitory effect of taurine on ouabain-induced arrythmia].
1975 Jan
Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects.
1977 Jul
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Brain renin-angiotensin system and ouabain-induced sympathetic hyperactivity and hypertension in Wistar rats.
1999 Jul
Different effects of in vivo ouabain and digoxin on renal artery function and blood pressure in the rat.
2000 Sep
The cardiac sodium pump: structure and function.
2002
Delta-Aminolevulinic acid transport in murine mammary adenocarcinoma cells is mediated by beta transporters.
2002 Aug 12
Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors.
2002 Nov
11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications.
2003 Apr
The renal-specific transporter mediates facilitative transport of organic anions at the brush border membrane of mouse renal tubules.
2004 Aug
Neurogenic nitric oxide release increases in mesenteric arteries from ouabain hypertensive rats.
2004 May
Contribution of the endothelin and renin-angiotensin systems to the vascular changes in rats chronically treated with ouabain.
2004 Nov
Ouabain-induced hypertension alters the participation of endothelial factors in alpha-adrenergic responses differently in rat resistance and conductance mesenteric arteries.
2004 Sep
[Renal sodium handling in ouabain-hypertensive rats].
2005 Aug
The alpha2-isoform of Na-K-ATPase mediates ouabain-induced hypertension in mice and increased vascular contractility in vitro.
2005 Feb
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
Alterations in structure and mechanics of resistance arteries from ouabain-induced hypertensive rats.
2006 Jul
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats].
2006 Oct
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
Visual behavior of adult goldfish with regenerating retina.
2007 May-Jun
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
Activation of BKCa channels by nitric oxide prevents coronary artery endothelial dysfunction in ouabain-induced hypertensive rats.
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
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
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
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 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
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 Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
WHO-VATC QC01AC01
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
Code System Code Type Description
MESH
D010042
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
CHEBI
472805
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
ECHA (EC/EINECS)
211-139-3
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
SMS_ID
100000076204
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
FDA UNII
5ACL011P69
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
HSDB
3519
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
ChEMBL
CHEMBL222863
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
PUBCHEM
439501
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
DRUG CENTRAL
2004
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
IUPHAR
4826
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
EVMPD
SUB14721MIG
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
RXCUI
7762
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
OUABAIN
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
DRUG BANK
DB01092
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
MERCK INDEX
M8270
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY Merck Index
CHEBI
145798
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
NSC
25485
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID0043765
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
CAS
630-60-4
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY
MERCK INDEX
M10252
Created by admin on Wed Jul 05 23:38:56 UTC 2023 , Edited by admin on Wed Jul 05 23:38:56 UTC 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY