STROPHANTHIDIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H32O6
Molecular Weight	404.4966
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@]3(O)C[C@@H](O)CC[C@]3(C=O)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@]24O)C5=CC(=O)OC5

InChI

InChIKey=ODJLBQGVINUMMR-HZXDTFASSA-N

InChI=1S/C23H32O6/c1-20-6-3-17-18(4-8-22(27)11-15(25)2-7-21(17,22)13-24)23(20,28)9-5-16(20)14-10-19(26)29-12-14/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3/t15-,16+,17-,18+,20+,21-,22-,23-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18954525
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9263917

Strophanthidin is a cardiotonic steroid that decreases the potassium content and raises the sodium content in rabbit renal cortex slices. In addition, strophanthidin induced two different types of membrane depolarization: a small, reversible depolarization with a peak amplitude of 4 +/- 2.6 mV or a prolonged depolarization of large amplitude (48.6 +/- 9.0 mV) with or without a decrease in apparent rat membrane resistance.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
sodium-potassium adenosine triphosphatase 1 Target ID: sodium-potassium adenosine triphosphatase Sources: https://www.ncbi.nlm.nih.gov/pubmed/9263917	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Pharmacology of ACC-9653 (phenytoin prodrug).	1989	2767010
Intracellular sodium and contractile function in hypertrophied human and guinea-pig myocardium.	2001 Apr	11374058
Na+,K(+)-ATPase inhibiting activity of cardiac glycosides from Erysimum cheiranthoides.	2001 Jun	11458460
Effect of nitric oxide on strophanthidin-induced ventricular tachycardia.	2001 May	11359997
Regulation of vocal fold transepithelial water fluxes.	2001 Sep	11509542
Experimental and modeling studies of novel bursts induced by blocking na(+) pump and synaptic inhibition in the rat spinal cord.	2002 Aug	12163521
Cardiac glycosides from Erysimum cheiranthoides.	2002 Jun	12045350
Importance of Ca2+ influx by Na+/Ca2+ exchange under normal and sodium-loaded conditions in mammalian ventricles.	2003 Jan	12619860
Block of Na+,K+-ATPase and induction of hybrid death by 4-aminopyridine in cultured cortical neurons.	2003 May	12606650
Determination of strophanthidin in ingesta and plant material by LC-MS/MS.	2004 Apr 21	15080617
Effects of purified endogenous inhibitor of the Na+/Ca2+ exchanger on ouabain-induced arrhythmias in the atria and ventricle strips of guinea pig.	2006 Dec 28	17078946
The inotropic effect of cardioactive glycosides in ventricular myocytes requires Na+-Ca2+ exchanger function.	2006 Sep 15	16825310
Rotenone potentiates NMDA currents in substantia nigra dopamine neurons.	2007 Jun 27	17560718
Mechanistic insight into the functional and toxic effects of Strophanthidin in the failing human myocardium.	2007 Nov	17956764
On the mechanisms of arrhythmias in the myocardium of mXinalpha-deficient murine left atrial-pulmonary veins.	2008 Aug 15	18644388
Different Na+/K+-ATPase signal pathways was involved in the increase of [Ca2+]i induced by strophanthidin in normal and failing isolated guinea pig ventricular myocytes.	2008 Nov	18954525
Neural agrin changes the electrical properties of developing human skeletal muscle cells.	2009 Feb	18807173
The non-gastric H,K-ATPase as a tool to study the ouabain-binding site in Na,K-ATPase.	2009 Jan	18324411
Outward Currents Contributing to Inspiratory Burst Termination in preBötzinger Complex Neurons of Neonatal Mice Studied in Vitro.	2010	21151816
Activation of the cardiac Na(+)-Ca(2+) exchanger by sorcin via the interaction of the respective Ca(2+)-binding domains.	2010 Jul	20298697

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Effect of strophanthidin (Str) on intracellular calcium concentration ([Ca2+]i) was investigated on isolated ventricular myocytes of guinea pig. The result showed that Str increased [Ca2+]i in a concentration-dependent manner. In Na+, K+ -free Tyrode' s solution, the response of cardiomycytes in [Ca2+]i elevation to Str (10 micromol L(-1)) was attenuated, while remained no change to Str (1 and 100 nmol L(-1)).

Name

Type

Language

STROPHANTHIDIN

Common Name

English

CARD-20(22)-ENOLIDE, 3,5,14-TRIHYDROXY-19-OXO-

Common Name

English

Strophanthin-k [WHO-DD]

Common Name

English

5.BETA.-CARD-20(22)-ENOLIDE, 3.BETA.,5,14-TRIHYDROXY-19-OXO-

Common Name

English

STROPHANTHIDIN [MI]

Common Name

English

(3.BETA.,5.BETA.)-3,5,14-TRIHYDROXY-19-OXOCARD-20(22)-ENOLIDE

Systematic Name

English

STROPHANTHIDIN K

Common Name

English

ERYSIMUPICRONE

Common Name

English

APOCYNAMARIN

Common Name

English

STROPHANTHIN-K

Common Name

English

NSC-86078

Code

English

STROPHANTHIDINE

Common Name

English

CORCHOSIDE A AGLYCON

Common Name

English

CYNOTOXIN

Common Name

English

CORCHORIN

Common Name

English

CORCHORGENIN

Common Name

English

ERYSIMUPIKRON

Common Name

English

K-STROPHANTHIDIN

Common Name

English

CONVALLATOXIGENIN

Common Name

English

CYMARIGENIN

Common Name

English

APOCYMARIN

Common Name

English

CORCHSULARIN

Common Name

English

Code System Code Type Description

NSC

86078