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
Intracellular sodium and contractile function in hypertrophied human and guinea-pig myocardium.	2001 Apr	11374058
Ca2+ mediates the effect of inhibition of Na+-K+-ATPase on the basolateral K+ channels in the rat CCD.	2001 Apr	11245609
Na+,K(+)-ATPase inhibiting activity of cardiac glycosides from Erysimum cheiranthoides.	2001 Jun	11458460
Hypoglycemia enhances ionotropic but reduces metabotropic glutamate responses in substantia nigra dopaminergic neurons.	2001 Mar	11247985
Ion transport and regulation of respiratory tract fluid output in dogs.	2001 Mar	11181589
Effect of nitric oxide on strophanthidin-induced ventricular tachycardia.	2001 May	11359997
Na(+)/Ca(2+) exchange and its role in intracellular Ca(2+) regulation in guinea pig detrusor smooth muscle.	2001 May	11287321
Rapid inhibition of the Na+-K+ pump affects Na+-Ca2+ exchanger-mediated relaxation in rabbit ventricular myocytes.	2001 May 15	11351025
Regulation of vocal fold transepithelial water fluxes.	2001 Sep	11509542
Pacing-induced spontaneous activity in myocardial sleeves of pulmonary veins after treatment with ryanodine.	2003 Apr 15	12668519
Importance of Ca2+ influx by Na+/Ca2+ exchange under normal and sodium-loaded conditions in mammalian ventricles.	2003 Jan	12619860
Measurement of the dissociation constant of Fluo-3 for Ca2+ in isolated rabbit cardiomyocytes using Ca2+ wave characteristics.	2003 Jul	12767887
Relationship between cardiotonic effects and inhibition on cardiac sarcolemmal Na+,K+-ATPase of strophan-thidin at low concentrations.	2003 Nov	14627493
Role of the electrogenic Na/K pump in disinhibition-induced bursting in cultured spinal networks.	2003 Nov	12890799
Electromechanical properties of Purkinje fiber strands isolated from human ventricular endocardium.	2004 Jun	15366435
Effects of sodium pump activity on spontaneous firing in neurons of the rat suprachiasmatic nucleus.	2006 Jul	16467417
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
Sodium pumps adapt spike bursting to stimulus statistics.	2007 Nov	17906619
Essential role of diastolic oscillatory potentials in adrenergic control of guinea pig sino-atrial node discharge.	2009 Nov 18	19922640
Activation of the cardiac Na(+)-Ca(2+) exchanger by sorcin via the interaction of the respective Ca(2+)-binding domains.	2010 Jul	20298697
Antiarol cinnamate and africanoside, a cinnamoyl triterpene and a hydroperoxy-cardenolide from the stem bark of Antiaris africana.	2010 Oct	20533166

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