Digitoxin
Title: Digitoxin
CAS Registry Number: 71-63-6
CAS Name: (3b,5b)-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]-14-hydroxycard-20(22)-enolide
Additional Names: digitalin, crystalline; digitophyllin
Trademarks: Carditoxin (Gedeon Richter); Coramedan (Medice); Cristapurat; Crystodigin (Lilly); Digicor (Hennig); Digilong (Boehringer, Mann.); Digimerck (Merck KGaA); Digimed (Trommsdorff); Digipural (Schaper & Brðmer); Ditaven (Cascan); Lanatoxin (Beiersdorf); Myodigin; Purodigin (Wyeth); Purpurid (Promonta); Tardigal (Beiersdorf)
Molecular Formula: C41H64O13
Molecular Weight: 764.94
Percent Composition: C 64.38%, H 8.43%, O 27.19%
Literature References: Secondary glycoside from Digitalis purpurea L., Scrophulariaceae. Extracted from the dried leaves with 50% alc. Extraction procedure: Cloetta, Arch. Exp. Pathol. Pharmakol. 112, 261 (1926). Purification: Windaus, Freese, Ber. 58, 2503 (1925). Ten kilo leaves yield about 6 grams pure digitoxin. Identity with digitophyllin: Cloetta, Arch. Exp. Pathol. Pharmakol. 88, 113 (1920). Structure: See reviews by Elderfield in Chem. Rev. 17, 187 (1935), and Stoll, The Cardiac Glycosides (London, 1937); also Shoppee in Annu. Rev. Biochem. 11, 103 (1942). Acid hydrolysis yields 1 mol digitoxigenin + 3 mol digitoxose. The sugar residue is attached to the hydroxyl group at C-3 of the aglycon. Structure of the sugar moiety: Lichti et al., Helv. Chim. Acta 45, 868 (1962). Digitoxin U.S.P. is either pure digitoxin or a mixture of cardioactive glycosides obtained from Digitalis purpurea and consisting chiefly of digitoxin. The potency of digitoxin U.S.P. corresp to the potency of an equal wt of U.S.P. Digitoxin Reference Standard. A deviation of 20% is permitted. The physical characteristics given below are those of the pure compd. Toxicity data: Foerster et al., Arch. Int. Pharmacodyn. Ther. 159, 1 (1966). Comprehensive description: I. M. Jakovljevic, Anal. Profiles Drug Subs. 3, 149-172 (1974).
Properties: Very small elongated, rectangular plates from dil alc. May contain ½ or 1 mol H2O or EtOH which is given up at 118° in vacuo. When anhydrous, mp 256-257°. [a]D20 +4.8° (c = 1.2 in dioxane). One gram dissolves in about 40 ml chloroform, about 60 ml alcohol, about 400 ml ethyl acetate. Also sol in acetone, amyl alcohol, pyridine, sparingly sol in ether, petr ether, water (1 g/100 liter at 20°). LD50 in guinea pigs, cats (mg/kg): 60.0, 0.18 orally (Foerster).
Melting point: mp 256-257°
Optical Rotation: [a]D20 +4.8° (c = 1.2 in dioxane)
Toxicity data: LD50 in guinea pigs, cats (mg/kg): 60.0, 0.18 orally (Foerster)
 
Derivative Type: Acetyl derivatives see Acetyldigitoxins
 
Therap-Cat: Cardiotonic.
Therap-Cat-Vet: Cardiotonic.
Keywords: Cardiotonic.

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