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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 of ACTODIGIN

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

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
Record UNII
9E4KL95FK9
Record Status Validated (UNII)
Record Version