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
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
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
Effects of cardiac glycosides on atrial fibrillation.	2001 Nov	11713174
Biphasic effect of cardiac glycosides on action potential duration in isolated Purkinje fibers.	2001 Sep	11589786
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
Discovery and development of anticancer agents from plants.	2002 Jul-Aug	12416027
Cardiac glycosides from Erysimum cheiranthoides.	2002 Jun	12045350
Intracellular Na(+) concentration is elevated in heart failure but Na/K pump function is unchanged.	2002 May 28	12034663
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
Evidence for a modulatory effect of external potassium ions on ionic current mediated by the cardiac Na+-Ca2+ exchanger.	2003 Jan	12526887
Block of Na+,K+-ATPase and induction of hybrid death by 4-aminopyridine in cultured cortical neurons.	2003 May	12606650
Relationship between cardiotonic effects and inhibition on cardiac sarcolemmal Na+,K+-ATPase of strophan-thidin at low concentrations.	2003 Nov	14627493
Ouabain binding to Na+,K+-ATPase relaxes cell attachment and sends a specific signal (NACos) to the nucleus.	2004 Apr 1	15216416
Determination of strophanthidin in ingesta and plant material by LC-MS/MS.	2004 Apr 21	15080617
Functional consequences of detubulation of isolated rat ventricular myocytes.	2004 Jun 1	15158145
Diurnal modulation of the Na+/K+-ATPase and spontaneous firing in the rat retinorecipient clock neurons.	2004 Oct	15381747
Arrhythmogenic mechanisms in the isolated perfused hypokalaemic murine heart.	2007 Jan	17280555
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
Evaluation of the toxicity of Adonis aestivalis in calves.	2007 Sep	17823409
On the mechanisms of arrhythmias in the myocardium of mXinalpha-deficient murine left atrial-pulmonary veins.	2008 Aug 15	18644388
Abnormalities of calcium metabolism and myocardial contractility depression in the failing heart.	2009 Dec	19434491
Reduced Ca2+ transport across sarcolemma but enhanced spontaneous activity in cardiomyocytes isolated from left atrium-pulmonary veins tissue of myopathic hamster.	2009 Dec 29	20040082
The non-gastric H,K-ATPase as a tool to study the ouabain-binding site in Na,K-ATPase.	2009 Jan	18324411
Essential role of diastolic oscillatory potentials in adrenergic control of guinea pig sino-atrial node discharge.	2009 Nov 18	19922640
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
Occurrence of progesterone and related animal steroids in two higher plants.	2010 Mar 26	20108949
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