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

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

CNS Active
3913
Curator's Comment: SMALL doses of ouabain have powerful central nervous depressant effects. Ouabain directly stimulates the PNS center in the brain

Originator

Arnaud, L.-A.
2
Curator's Comment: Ouabain was discovered and so named in 1888 by Amaud

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Sodium/potassium-transporting ATPase subunit alpha-2
4
Target ID: P50993
Gene ID: 477.0
Gene Symbol: ATP1A2
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 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)
Inhibitor
8297
 15.0 nM [Ki]
Inhibitor
8297
 63.0 nM [IC50]
Inhibitor
8297
 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)
Inhibitor
8297
 50.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Ouabain

Approved Use

Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Primary
Approved
8429
Ouabain

Approved Use

Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Primary
Approved
8429
Ouabain

Approved Use

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

PubMed

TitleDatePubMed
Ouabain-induced ventricular tachycardia and its effect on the performance and metabolism of the dog heart.
1959 Sep
Antiarrhythmic and antifibrillatory properties of aprindine.
1975 Aug
Effect of hypomagnesemia on ouabain-induced cardiac arrhythmias in dogs.
1975 Jul
[Comparison of antiarrhythmic effects of IHC-72 (an iodonium-72), lidocaine and verapamil].
1992
Brain renin-angiotensin system and ouabain-induced sympathetic hyperactivity and hypertension in Wistar rats.
1999 Jul
Chronic hypertension induced by ouabain but not digoxin in the rat: antihypertensive effect of digoxin and digitoxin.
2000 Sep
Neuronal Fos-like immunoreactivity in ouabain-induced hypertension.
2000 Sep 8
Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides.
2002 Apr
Delta-Aminolevulinic acid transport in murine mammary adenocarcinoma cells is mediated by beta transporters.
2002 Aug 12
Effects of some transmitters on resting membrane potential of somatic cell in Lumbricus terrestris muscle wall.
2003 Aug
[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
[Comparative analysis of the cardiac glycosides action on the growth of the cardiac tissue explants].
2005 Nov
[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
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
Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes.
2008 Feb 2
Structural and functional characteristic of a model for deep-seated lacunar infarct in rats.
2008 Oct 15
Extracellular signal regulated kinase 5 mediates signals triggered by the novel tumor promoter palytoxin.
2009 Dec 1
Chronic ouabain treatment induces vasa recta endothelial dysfunction in the rat.
2009 Jan
Low-dose ouabain constricts small arteries from ouabain-hypertensive rats: implications for sustained elevation of vascular resistance.
2009 Sep
DNA damage after intracerebroventricular injection of ouabain in rats.
2010 Feb 26
Dopamine-mediated inhibition of renal Na+/K+-ATPase in HK-2 cells is reduced by ouabain.
2010 May
Patents

Patents

04906467
2
04922021
2
JP1060373A
2
JP2001017196A
2
JP2002255822A
8
JP2002536415A
10
JP2006523667A
4
JP2007186477A
2
JP2009541410A
2
JP2010530745A
4
JP4729259B2
38
JPH00833481A
2
JPH02104595A
2
JPH02186982A
2
JPH02242671A
2
JPH02245183A
2
JPH02245184A
2
JPH02245185A
2
JPH02245186A
2
JPH0314539A
2
JPH03228692A
2
JPH03292896A
8
JPH04141086A
2
JPH053784A
2
JPH0597708A
2
JPH08308571A
2
JPH0833481A
2
JPH08336384A
2
JPH08501298A
3
JPH0899894A
6
JPH10114799A
2
JPH10177024A
2
JPS57165356A
2
JPS6089426A
2
JPS61242574A
2
JPS62155083A
2

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.
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
ACTIVE MOIETY
Structure of OUABAIN
SALT/SOLVATE (PARENT)
Structure of OUABAIN OCTAHYDRATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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