3167. Digoxin

Nomenclature

CAS number: 20830-75-5
(3β,5β,12β)-3-[(O-2,6-Dideoxy-β-d-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-d-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-d-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide; Digacin (Beiersdorf-Lilly); Dilanacin (AWD); Eudigox (Simes); Lanicor (Roche); Lanoxin (GSK); Lanoxicaps (GSK); Lenoxin (GSK); Neo-Dioxanin (Boehringer, Ing.); Rougoxin (Rougier).
C41H64O14; mol wt 780.94.
C 63.06%, H 8.26%, O 28.68%.

Description and references

Secondary glycoside from Digitalis lanata Ehrh., or D. orientalis Lam., Scrophulariaceae: S. Smith, J. Chem. Soc. 1930, 508; Stoll, The Cardiac Glycosides (London, 1937); M. M. Dhar et al., IN 62497 (1958 to Council Sci. Indust. Res.), C.A. 53, 653b (1959). See also ref under Digoxigenin. Acid hydrolysis of digoxin yields 1 mol digoxigenin + 3 mols digitoxose. The sugar residue is attached to the hydroxyl group at C-3 of the aglycon. Clinical pharmacokinetics: J. K. Aronson, Clin. Pharmacokinet. 5, 137 (1980). Comprehensive description: P. R. B. Foss, S. A. Benezra, Anal. Profiles Drug Subs. 9, 207-243 (1980).

Properties

Radially arranged, four- and five-sided triclinic plates from dil alcohol or dil pyridine, decomp 230-265°. [α]25Hg +13.4 to 13.8° (c = 10 in pyridine). uv max (ethanol): 220 nm (ε 12800). Sol in dil alcohol, pyridine, or mixt of chloroform and alcohol. Almost insol in ether, acetone, ethyl acetate, chloroform, water. More sol in hot 80% alcohol than gitoxin.

Derivative

β-Methyldigoxin.

Nomenclature

CAS number: 30685-43-9
Medigoxin; metildigoxin; 4'''-O-methyldigoxin; 3β,12β,14β-trihydroxy-5β-card-20(22)-enolide-3-(4'''-O-methyltridigitoxoside); Cardiolan (Tosi); Lanirapid (Roche); Lanitop (Roche).
C42H66O14; mol wt 794.97.
C 63.46%, H 8.37%, O 28.18%.

Description and references

Obtained by the O-methylation of digoxin: F. Kaiser et al., ZA 6806079; eidem, US 3538078 (1969, 1970 both to Boehringer, Mann.). Pharmacology and toxicity studies: W. Schaumann, R. Wegerle, Arzneim.-Forsch. 21, 225 (1971); H. Czerwek et al., ibid. 231.

Properties

Crystals, mp 227-231°. LD50 in rats, mice (mg/kg): 4.8, 4.9 i.v.; 6.2, 4.8 i.p.; 8.3, 7.8 orally (Czerwek).

Derivative

α-Acetyldigoxin.

Nomenclature

CAS number: 5511-98-8
Lanatilin (Wabosan); Sandolanid (Sandoz).
C43H66O15; mol wt 822.98.
C 62.75%, H 8.08%, O 29.16%.

Properties

Obtained by enzymatic hydrolysis of digilanide. Prisms from methanol + chloroform, dec 225°. [α]D20 +18.9° (pyridine). Very sparingly sol in ethyl acetate.

Derivative

β-Acetyldigoxin.

Nomenclature

CAS number: 5355-48-6
Kardiamed (Medice); Longdigox (Trommsdorff); Novodigal (Beiersdorf-Lilly); Stillacor (Wolff).

Properties

Needles from alcohol + chloroform, dec 240°. [α]D20 +30.4° (c = 1.2 in alc). More sol in ethyl acetate than the α-form.

Therapeutic Category

Cardiotonic.

Therapeutic Category (Veterinary)

Cardiotonic.

Keywords

Cardiotonic