β-Methyl Digoxin

• CAT Number: R012706
• CAS Number: 30685-43-9
• Molecular Formula: C42H66O14
• Molecular Weight: 794.976
• Purity: ≥95%
• Synonyms: (3β,5β,12β)-3-[(O-2,6-Dideoxy-4-O-methyl-β-D-ribo-hexopyranosyl-(14)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(14)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide; 4’’’-Methyldigoxin; 4’’’-O-Methyldigoxin; Lanirapid; Lanitop; M
• Storage: -20°C
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• InChI: InChI=1S/C42H66O14/c1-20-37(49-6)29(43)16-35(51-20)55-39-22(3)53-36(18-31(39)45)56-38-21(2)52-34(17-30(38)44)54-25-9-11-40(4)24(14-25)7-8-27-28(40)15-32(46)41(5)26(10-12-42(27,41)48)23-13-33(47)50-19-23/h13,20-22,24-32,34-39,43-46,48H,7-12,14-19H2,1-6H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m1/s1
• InChIKey: IYJMSDVSVHDVGT-PEQKVOOWSA-N
• SMILES: CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CC(C7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)C)O)OC

β-Methyl Digoxin (CAS 30685-43-9) is a cardiotonic methylated digoxin derivative with enhanced and more complete gastrointestinal absorption. It can be used in the treatment of congestive heart failure and cardiac arrhythmia.

Reference

1. Hunter, J., et al., 1993. Functional expression of P-glycoprotein in apical membranes of human intestinal Caco-2 cells. Kinetics of vinblastine secretion and interaction with modulators. The Journal of biological chemistry. 268(20): 14991-7. PMID: 8100817
2. Greiner, B., et al., 1999. The role of intestinal P-glycoprotein in the interaction of digoxin and rifampin. The Journal of clinical investigation. 104(2): 147-53. PMID: 10411543
3. Jun, A S., et al., . High-performance liquid chromatography assay of amiodarone in rat plasma. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Société canadienne des sciences pharmaceutiques. 4(3): 263-8. PMID: 11737993
4. Sugiyama, Daisuke., et al., 2002. Effect of 17 beta-estradiol-D-17 beta-glucuronide on the rat organic anion transporting polypeptide 2-mediated transport differs depending on substrates. Drug metabolism and disposition: the biological fate of chemicals. 30(2): 220-3. PMID: 11792694
5.Rennekamp, H., et al. "Pharmacokinetic behaviour of 4‴-methyldigoxin in man." Naunyn-Schmiedeberg's archives of pharmacology 273.1-2 (1972): 172-174.