ACTODIGIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H44O9
Molecular Weight	536.6543
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]6(O[C@H]1CC[C@@]2(C)[C@]([H])(CC[C@]3([H])[C@]2([H])CC[C@]4(C)[C@H](CC[C@]34O)C5=CCOC5=O)C1)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O

InChI

InChIKey=ACLJAFRNPZVVIW-ADFGDECNSA-N

InChI=1S/C29H44O9/c1-27-9-5-16(37-26-24(33)23(32)22(31)21(14-30)38-26)13-15(27)3-4-20-19(27)6-10-28(2)18(7-11-29(20,28)35)17-8-12-36-25(17)34/h8,15-16,18-24,26,30-33,35H,3-7,9-14H2,1-2H3/t15-,16+,18-,19+,20-,21-,22-,23+,24-,26-,27+,28-,29+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H44O9
Molecular Weight	536.6543
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	13 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/891095 | https://www.ncbi.nlm.nih.gov/pubmed/921406

Actodigin is a semisynthetic cardiac glycoside compounded from digitoxigenin and one molecule of glucose. In addition, unlike the naturally occurring glycosides, the C-2 instead of the C-3 atom of the lactone ring is attached to the steroid nucleus. Actodigin is a cardiovascular agent. When injected at 30 min invervals into dogs with barbiturate-induced heart failure, actodigin caused a marked positive inotropic action of short duration. It converted arrhythmia to normal sinus rhythm. Actodigin effectively and quickly reduced the ventricular rate in patients with atrial fibrillation. Actodigin, because of its rapid onset and brief duration of action, may be useful in controlling the ventricular rate in patients with atrial fibrillation.

Approval Year

PubMed

Title	Date	PubMed
A crystallographic, conformational energy, and biological study of Actodigin (AY-22,241) and its genin.	1980 Jan	6247637

Patents

Sample Use Guides

In Vivo Use Guide

Four patients with the recent onset of atrial fibrillation and a rapid ventricular rate who required digitalis were studied. patients (l to 3) were given actodigin by an intermittent intravenous regimen, a dose given every 10 min. The first dose was 0.01 mg/kg, the second dose was 0.025 mg/kg, and subsequent doses were 0.05 mg/kg. The fourth patient received actodigin by constant intravenous infusion. The initial infusion, at a rate of 0.003 mg/kg/min, was continued for 20 min after which it was raised in increments of 0.001 mg/kg/min every 20 min.

Route of Administration: Intravenous

In Vitro Use Guide

In experiments on contractility of cat papillary muscle, Actodigin (2 times 10(-7) to 4 times 10(-6) M) produced a dose-dependent positive inotropic effect, a marked increase in the maximum rate of force development, and no change in resting tension.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:59:25 GMT 2023` Edited by `admin` on `Sat Dec 16 15:59:25 GMT 2023`
Record UNII	9E4KL95FK9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACTODIGIN

Official Name

English

AY-22241

Code

English

AY 22,241

Code

English

3.BETA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-14,23-DIHYDROXY-24-NOR-5.BETA.,14.BETA.-CHOL-20(22)-EN-21-OIC ACID .GAMMA.-LACTONE

Common Name

English

actodigin [INN]

Common Name

English

ACTODIGIN [USAN]

Common Name

English

NSC-53396

Code

English

AY 22241

Code

English

AY-22,241

Code

English

24-NOR-5,14-CHOL-20(22)-EN-21-OIC ACID, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-14,23-DIHYDROXY-, .GAMMA.-LACTONE, (3.BETA.,5.BETA.,14.BETA.)-

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL2103957