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 & Brmer); 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.
Digitoxose Diglyme Digoxigenin Dihexyverine Dihydralazine

Digitoxin
Digitoxin.png
Systematic (IUPAC) name
(3β,5β)-3-[(O-2,6-dideoxy-
β-D-ribo-hexapyranosyl-(1->4)-
2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-
14-hydroxycard-20(22)-enolide
Clinical data
Trade names Digitaline
Legal status  ?
Pharmacokinetic data
Bioavailability 95% (Oral)
Metabolism Liver
Half-life 5~7 days
Identifiers
CAS number 71-63-6 YesY
ATC code C01AA04
PubChem CID 441207
DrugBank DB01396
ChemSpider 389987 N
UNII E90NZP2L9U N
KEGG D00297 N
ChEBI CHEBI:28544 N
ChEMBL CHEMBL254219 N
Chemical data
Formula C41H64O13 
Mol. mass 764.939 g/mol
 N (what is this?)  (verify)

Digitoxin is a cardiac glycoside. It has similar structure and effects to digoxin (though the effects are longer-lasting). Unlike digoxin (which is eliminated from the body via the kidneys), it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current Western medical practice. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.[1]