OUABAIN OCTAHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H44O12.8H2O
Molecular Weight	728.7747
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.O.O.O.O.O.O.[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=TYBARJRCFHUHSN-DMJRSANLSA-N

InChI=1S/C29H44O12.8H2O/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;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1

HIDE SMILES / InChI

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 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) Sources: http://www.selleckchem.com/products/ouabain.html	Inhibitor 8297	15.0 nM [Ki]
PC-3 15 Target ID: CHEMBL390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	Inhibitor 8297	63.0 nM [IC50]
A549 13 Target ID: CHEMBL392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621895	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) Sources: https://www.drugbank.ca/drugs/DB01092	Inhibitor 8297	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 8429	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 8429	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 8429	Ouabain Approved Use Ouabain is primarily indicated in conditions like Atrial fibrillation, Atrial flutter, Cardiac arrhythmia, Left ventricular failure, Ventricular arrhythmias.
Unknown 2578

PubMed

Title	Date	PubMed
The effect of diphenylhydantoin sodium (dilantin), procaine hydrochloride, procaine amide hydrochloride, and quinidine hydrochloride upon ouabain-induced ventricular tachycardia in unanesthetized dogs.	1954 Jul	13172862
Antiarrhythmic and antifibrillatory properties of aprindine.	1975 Aug	1151768
[Inhibitory effect of taurine on ouabain-induced arrythmia].	1975 Jan	125678
Effect of hypomagnesemia on ouabain-induced cardiac arrhythmias in dogs.	1975 Jul	1213789
Antiarrhythmic and hemodynamic effects of an aminosteroid (Org 3001) in the digitalized dog.	1976 Mar	1261591
Association of in vivo and in vitro propranolol levels in canine Purkinje fibers with antiarrhythmic effects.	1977 Jul	17729
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Effects of AH-1058, a new antiarrhythmic drug, on experimental arrhythmias and cardiac membrane currents.	1999 Apr	10218734
Synaptic plasticity in sympathetic ganglia from acquired and inherited forms of ouabain-dependent hypertension.	2001 Aug	11448869
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity.	2001 Sep 1	11517236
Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides.	2002 Apr	11929882
Alterations in phenylephrine-induced contractions and the vascular expression of Na+,K+-ATPase in ouabain-induced hypertension.	2002 Feb	11834625
Ouabain-induced hypertension is accompanied by increases in endothelial vasodilator factors.	2002 Nov	12384489
Tumour-specific activation of the sodium/iodide symporter gene under control of the glucose transporter gene 1 promoter (GTI-1.3).	2003 May	12541134
Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump.	2004 Mar	15009217
Biotin uptake by human proximal tubular epithelial cells: cellular and molecular aspects.	2005 Apr	15561972
[Comparative study of properties of Na+, K+-ATPase and Mg2+-ATPase of the myometrium plasma membrane].	2005 Mar-Apr	16335235
Functional heterogeneity of the "transporter" of electrogenic ionic pump of the Lumbricus terrestris somatic myocyte membrane.	2006 Dec	17603680
Enhanced sensitivity of DJ-1-deficient dopaminergic neurons to energy metabolism impairment: role of Na+/K+ ATPase.	2006 Jul	16624565
[Changes in renal sodium transport during hypertension development in ouabain-hypertensive rats].	2006 Oct	17062336
Ouabain-induced hypertension enhances left ventricular contractility in rats.	2006 Sep 13	16716361
Endogenous brain Na pumps, brain ouabain-like substance and the alpha2 isoform in salt-dependent hypertension.	2007 Dec	17980562
Visual behavior of adult goldfish with regenerating retina.	2007 May-Jun	17592671
Hepatocyte growth factor increases uptake of estradiol 17beta-D-glucuronide and Oatp1 protein level in rat hepatocytes.	2008 Feb 2	18031729
Proteomics investigation of protein expression changes in ouabain induced apoptosis in human umbilical vein endothelial cells.	2008 Jun 1	18247327
Response of sodium pump to ouabain challenge in human glioblastoma cells in culture.	2009	19995221
DNA damage after intracerebroventricular injection of ouabain in rats.	2010 Feb 26	20056132

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.

Name

Type

Language

OUABAIN OCTAHYDRATE

Common Name

English

NSC-757425

Code

English

STROPHOPERM

Brand Name

English

CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-1,5,11,14,19-PENTAHYDROXY-, OCTAHYDRATE, (1.BETA.,3.BETA.,5.BETA.,11.ALPHA.)-

Common Name

English

ACOCANTHERIN OCTAHYDRATE

Common Name

English

STRODIVAL

Brand Name

English

PUROSTROPHAN

Brand Name

English

Code System Code Type Description

EPA CompTox

DTXSID7040730