Digitoxin

Digitoxin is a cardiac glycoside that has been found in Digitalis and has diverse biological activities. It inhibits human recombinant alpha1beta1, alpha2beta2, and alpha3beta1 subunit-containing Na+/K+-ATPases with Ki values of 250, 63, and 136 nM, respectively. Digitoxin inhibits the human-ether-a-go-go (hERG) potassium channel, also known as Kv11.1, in HEK293 cells expressing hERG (IC50 = 11.1 nM). It enhances developed tension and contractile force in electrically stimulated isolated guinea pig left atrial muscle when used at concentrations of 0.2 and 0.4 µM, respectively. Dietary administration of digitoxin (~1 mg/kg per day) attenuates congestive heart failure and reduces myocardial hypertrophy in a rat model of myocardial infarction induced by coronary artery ligation. Digitoxin is also cytotoxic to a panel of 10 human cancer cell lines, including myeloma, lymphoma, and leukemia cancer cells, with IC50 values ranging from 12 to 76 nM. Formulations containing digitoxin have previously been used in the treatment of congestive heart failure and cardiac arrhythmias.Formal Name: (3beta,5beta)-3-[(O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-14-hydroxy-card-20(22)-enolide. CAS Number: 71-63-6. Synonyms: Digitoxoside, Lanatoxin, NSC 7529. Molecular Formula: C41H64O13. Formula Weight: 765.0. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Chloroform: 20mg/mL, DMF: 25 mg/ml, DMF:PBS (pH 7.2) (1:1): 0.5 mg/ml, DMSO: 20 mg/ml, Ethanol: 5 mg/ml. lambdamax: 217 nm. SMILES: C[C@@]12[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@]3(O)CC[C@@H]4C(CO5)=CC5=O)([H])C[C@@H](O[C@]6([H])O[C@H](C)[C@@H](O[C@@]7([H])C[C@H](O)[C@H](O[C@]8([H])O[C@H](C)[C@@H](O)[C@@H](O)C8)[C@@H](C)O7)[C@@H](O)C6)CC1. InChi Code: InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1. InChi Key: WDJUZGPOPHTGOT-XUDUSOBPSA-N. Origin: Plant/Digitalis lanata.