ACETYLSTROPHANTHIDIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H34O7
Molecular Weight	446.5333
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](CC[C@]3(C=O)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@]24O)C5=CC(=O)OC5)OC(C)=O

InChI

InChIKey=JLZAERUVCODZQO-VWCUIIQSSA-N

InChI=1S/C25H34O7/c1-15(27)32-17-3-8-23(14-26)19-4-7-22(2)18(16-11-21(28)31-13-16)6-10-25(22,30)20(19)5-9-24(23,29)12-17/h11,14,17-20,29-30H,3-10,12-13H2,1-2H3/t17-,18+,19-,20+,22+,23-,24-,25-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H34O7
Molecular Weight	446.5333
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/239798 | https://www.ncbi.nlm.nih.gov/pubmed/6371896 | https://www.ncbi.nlm.nih.gov/pubmed/13309667

semisynthetic C3 acetyl ester of the aglycone strophanthidin. Acetylstrophanthidin inhibits sodium-potassium adenosinetriphosphatase (Na -K ATPase) and causes an inotropic effect. The effect of acetylstrophanthidin is first seen within half a minute to five minutes and becomes maximal in about ten minutes. This rapid action obviates the effect of time, which is so important for subsidence of precipitationg causes of cardiac failure. Severe pulmonic, coronary, and aortic valvular disease, as well as old age, tended to predispose the patients to unusual acetylstrophanthidin sensitivity. Acetylstrophanthidin may cause nausea and vomiting.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase (Oryctolagus cuniculus) 1 Target ID: Sodium/potassium-transporting ATPase (Oryctolagus cuniculus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/239798	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acute myocardial infarction 37 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8225670 https://www.ncbi.nlm.nih.gov/pubmed/13309667	Primary	Phase II 1132	Unknown Approved Use Unknown
Congestive heart failure 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13309667 https://www.ncbi.nlm.nih.gov/pubmed/13649555 https://www.ncbi.nlm.nih.gov/pubmed/13631061	Primary	Not Provided 504	Unknown Approved Use Unknown
Coronary artery disease 48 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2316465 https://www.ncbi.nlm.nih.gov/pubmed/13309667	Primary	Not Provided 504	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
2.7 mg 4 times / hour multiple, intravenous (total daily dose) Highest studied dose Dose: 2.7 mg, 4 times / hour Route: intravenous Route: multiple Dose: 2.7 mg, 4 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/13309667	unhealthy, ADULT n = 30 Health Status: unhealthy Condition: heart disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/13309667	Other AEs: ventricular bigemin... Other AEs: ventricular bigemin (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/13309667

AEs

AE	Significance	Dose	Population
ventricular bigemin	1 pt	2.7 mg 4 times / hour multiple, intravenous (total daily dose) Highest studied dose Dose: 2.7 mg, 4 times / hour Route: intravenous Route: multiple Dose: 2.7 mg, 4 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/13309667	unhealthy, ADULT n = 30 Health Status: unhealthy Condition: heart disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/13309667

Sourcing

Vendor/Aggregator	ID	URL
IBScreen	STOCK1N-52599
MolPort	MolPort-001-742-530	https://www.molport.com/shop/molecule-link/MolPort-001-742-530
TimTec	ST50309391	http://www.echemstore.com/catalogsearch/result/?q=ST50309391
eMolecules	4823878	https://orderbb.emolecules.com/search/#?query=4823878

PubMed

Title	Date	PubMed
Transient changes in plasma digoxin concentration and the development of cardiotoxicity.	1977 Nov	588806

Patents

Sample Use Guides

In Vivo Use Guide

The initial dose varied from 0.15 to 0.6 mg. Subsequent doses, if given, varied from 0.1 to 0.6 mg at intervals of one to fifteen minutes.

Route of Administration: Intravenous

In Vitro Use Guide

Acetylstrophanthidin (ACS, 4 uM) alters Ca(2+) transients in completely Na(+)-free conditions in intact ferret and cat ventricular myocytes. In intact ferret myocytes (stimulated at 0.2 Hz), ACS enhanced Ca(2+) transients and cell shortening during twitches. Acute inotropic effects of ACS depend on the presence of Na(+) and a functional Na(+)-Ca(2+) exchanger in ferret and cat myocytes (rather than alternate Na(+)-independent mechanisms).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:42:56 GMT 2023` Edited by `admin` on `Sat Dec 16 10:42:56 GMT 2023`
Record UNII	JG33H36364
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETYLSTROPHANTHIDIN

Common Name

English

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

Systematic Name

English

3-ACETYL-STROPHANTHIDIN

Common Name

English

ERYSIMUPICRONE ACETATE

Common Name

English

STROPHANTHIDIN ACETATE

Common Name

English

STROPHANTHIDIN 3-ACETATE

Common Name

English

NSC-92954

Code

English

Code System Code Type Description

CHEBI

59028