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

Molecular Formula	C23H32O6
Molecular Weight	404.4966
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
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
Effects of cardiac glycosides on atrial fibrillation.	2001 Nov	11713174
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
Beta 2-adrenergic regulation of ciliary beat frequency in rat bronchiolar epithelium: potentiation by isosmotic cell shrinkage.	2004 Jan 15	14594991
Diurnal modulation of the Na+/K+-ATPase and spontaneous firing in the rat retinorecipient clock neurons.	2004 Oct	15381747
The effects induced by the sulphonylurea glibenclamide on the neonatal rat spinal cord indicate a novel mechanism to control neuronal excitability and inhibitory neurotransmission.	2007 Jan	17128288
On the mechanisms of arrhythmias in the myocardium of mXinalpha-deficient murine left atrial-pulmonary veins.	2008 Aug 15	18644388
Effects of strophanthidin on intracellular calcium concentration in ventricular myocytes of guinea pig.	2008 Mar	18630261
Inhibition of the sodium potassium adenosine triphosphatase pump sensitizes cancer cells to anoikis and prevents distant tumor formation.	2009 Apr 1	19293189
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)).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:29:23 GMT 2023` Edited by `admin` on `Fri Dec 15 16:29:23 GMT 2023`
Record UNII	W5O632DN33
Record Status	`Validated (UNII)`
Record Version

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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