Digoxin
Title: Digoxin
CAS Registry Number: 20830-75-5
CAS Name: (3b,5b,12b)-3-[(O-2,6-Dideoxy-b-D-ribo-hexopyranosyl-(1®4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide
Trademarks: Digacin (Beiersdorf-Lilly); Dilanacin (AWD); Eudigox (Simes); Lanicor (Roche); Lanoxin (GSK); Lanoxicaps (GSK); Lenoxin (GSK); Neo-Dioxanin (Boehringer, Ing.); Rougoxin (Rougier)
Molecular Formula: C41H64O14
Molecular Weight: 780.94
Percent Composition: C 63.06%, H 8.26%, O 28.68%
Literature 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°. [a]25Hg +13.4 to 13.8° (c = 10 in pyridine). uv max (ethanol): 220 nm (e 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.
Optical Rotation: [a]25Hg +13.4 to 13.8° (c = 10 in pyridine)
Absorption maximum: uv max (ethanol): 220 nm (e 12800)
 
Derivative Type: b-Methyldigoxin
CAS Registry Number: 30685-43-9
Additional Names: Medigoxin; metildigoxin; 4¢¢¢-O-methyldigoxin; 3b,12b,14b-trihydroxy-5b-card-20(22)-enolide-3-(4¢¢¢-O-methyltridigitoxoside)
Trademarks: Cardiolan (Tosi); Lanirapid (Roche); Lanitop (Roche)
Molecular Formula: C42H66O14
Molecular Weight: 794.97
Percent Composition: C 63.46%, H 8.37%, O 28.18%
Literature 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).
Melting point: mp 227-231°
Toxicity data: 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 Type: a-Acetyldigoxin
CAS Registry Number: 5511-98-8
Trademarks: Lanatilin (Wabosan); Sandolanid (Sandoz)
Molecular Formula: C43H66O15
Molecular Weight: 822.98
Percent Composition: C 62.75%, H 8.08%, O 29.16%
Properties: Obtained by enzymatic hydrolysis of digilanide. Prisms from methanol + chloroform, dec 225°. [a]D20 +18.9° (pyridine). Very sparingly sol in ethyl acetate.
Optical Rotation: [a]D20 +18.9° (pyridine)
 
Derivative Type: b-Acetyldigoxin
CAS Registry Number: 5355-48-6
Trademarks: Kardiamed (Medice); Longdigox (Trommsdorff); Novodigal (Beiersdorf-Lilly); Stillacor (Wolff)
Properties: Needles from alcohol + chloroform, dec 240°. [a]D20 +30.4° (c = 1.2 in alc). More sol in ethyl acetate than the a-form.
Optical Rotation: [a]D20 +30.4° (c = 1.2 in alc)
 
Therap-Cat: Cardiotonic.
Therap-Cat-Vet: Cardiotonic.
Keywords: Cardiotonic.

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