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MedKoo Cat#: 598307 | Name: Digoxin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Digoxin is a cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small.

Chemical Structure

Digoxin
Digoxin
CAS#20830-75-5 (free)

Theoretical Analysis

MedKoo Cat#: 598307

Name: Digoxin

CAS#: 20830-75-5 (free)

Chemical Formula: C41H64O14

Exact Mass: 780.4296

Molecular Weight: 780.94

Elemental Analysis: C, 63.06; H, 8.26; O, 28.68

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
1g USD 650.00 2 Weeks
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Related CAS #
5511-98-8 (acetyl) 20830-75-5 (free)
Synonym
Digoxin; Dixina; HSDB 214; Novodigal; Lanoxin PG; SK-Digoxin; SK Digoxin; Cardiogoxin; NSC-95100; NSC95100; NSC 95100;
IUPAC/Chemical Name
4-((3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-(((2R,4S,5S,6R)-5-(((2S,4S,5S,6R)-5-(((2S,4S,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
InChi Key
LTMHDMANZUZIPE-PUGKRICDSA-N
InChi Code
InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
SMILES Code
C[C@H]1O[C@@H](O[C@H]2[C@H](C[C@@H](O[C@@H]2C)O[C@H]3[C@H](C[C@@H](O[C@@H]3C)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5C[C@H]([C@@]7([C@@H](C8=CC(OC8)=O)CC[C@]67O)C)O)C)O)O)C[C@@H]([C@@H]1O)O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Digoxin (NSC 95100) is a classical Na,K-ATPase inhibitor, with selectivity for the α2β3 isoform over the common α1β1 isoform, used in the treatment of atrial fibrillation and heart failure.
In vitro activity:
As shown in Figure 1A and B, the viability of HCT8 and SW620 cells decreased in a dose-dependent manner after exposure to digoxin at a concentration of 0.001–0.5 μM for 24 h, with half maximal inhibitory concentration (IC50) values of 0.15 and 0.23 µM for the HCT8 and SW620 cells, respectively. Furthermore, digoxin treatment reduced the number and size of the cell colonies, confirming that digoxin inhibited the proliferation of HCT8 and SW620 cells in a dose-dependent manner, as shown in Figure 1C and F. Reference: Gastroenterol Rep (Oxf). 2020 Dec 10;8(6):465-475. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7793120/
In vivo activity:
Collectively, these data indicate that digoxin effectively protects chronic hepatic damage, steatosis, and inflammation in HFD-induced obese mice. Thus, this study concludes that long-term treatment with oral digoxin reduces chronic liver damage, steatosis, and inflammation in experimental model of NASH. Reference: Am J Physiol Gastrointest Liver Physiol. 2019 Oct 1;317(4):G387-G397. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6842989/
Solvent mg/mL mM
Solubility
DMSO 69.4 88.82
DMF 30.0 38.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 780.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hou YQ, Wang YY, Wang XC, Liu Y, Zhang CZ, Chen ZS, Zhang Z, Wang W, Kong DX. Multifaceted anti-colorectal tumor effect of digoxin on HCT8 and SW620 cells in vitro. Gastroenterol Rep (Oxf). 2020 Dec 10;8(6):465-475. doi: 10.1093/gastro/goaa076. PMID: 33442480; PMCID: PMC7793120. 2. Saeed H, Mateen S, Moin S, Khan AQ, Owais M. Cardiac glycoside digoxin ameliorates pro-inflammatory cytokines in PBMCs of rheumatoid arthritis patients in vitro. Int Immunopharmacol. 2020 Feb 24;82:106331. doi: 10.1016/j.intimp.2020.106331. Epub ahead of print. PMID: 32106058. 3. Zhao P, Han SN, Arumugam S, Yousaf MN, Qin Y, Jiang JX, Torok NJ, Chen Y, Mankash MS, Liu J, Li J, Iwakiri Y, Ouyang X. Digoxin improves steatohepatitis with differential involvement of liver cell subsets in mice through inhibition of PKM2 transactivation. Am J Physiol Gastrointest Liver Physiol. 2019 Oct 1;317(4):G387-G397. doi: 10.1152/ajpgi.00054.2019. Epub 2019 Aug 14. PMID: 31411894; PMCID: PMC6842989. 4. McGill JL, Guerra-Maupome M, Schneider S. Prophylactic digoxin treatment reduces IL-17 production in vivo in the neonatal calf and moderates RSV-associated disease. PLoS One. 2019 Mar 25;14(3):e0214407. doi: 10.1371/journal.pone.0214407. PMID: 30908540; PMCID: PMC6433258.
In vitro protocol:
1. Hou YQ, Wang YY, Wang XC, Liu Y, Zhang CZ, Chen ZS, Zhang Z, Wang W, Kong DX. Multifaceted anti-colorectal tumor effect of digoxin on HCT8 and SW620 cells in vitro. Gastroenterol Rep (Oxf). 2020 Dec 10;8(6):465-475. doi: 10.1093/gastro/goaa076. PMID: 33442480; PMCID: PMC7793120. 2. Saeed H, Mateen S, Moin S, Khan AQ, Owais M. Cardiac glycoside digoxin ameliorates pro-inflammatory cytokines in PBMCs of rheumatoid arthritis patients in vitro. Int Immunopharmacol. 2020 Feb 24;82:106331. doi: 10.1016/j.intimp.2020.106331. Epub ahead of print. PMID: 32106058.
In vivo protocol:
1. Zhao P, Han SN, Arumugam S, Yousaf MN, Qin Y, Jiang JX, Torok NJ, Chen Y, Mankash MS, Liu J, Li J, Iwakiri Y, Ouyang X. Digoxin improves steatohepatitis with differential involvement of liver cell subsets in mice through inhibition of PKM2 transactivation. Am J Physiol Gastrointest Liver Physiol. 2019 Oct 1;317(4):G387-G397. doi: 10.1152/ajpgi.00054.2019. Epub 2019 Aug 14. PMID: 31411894; PMCID: PMC6842989. 2. McGill JL, Guerra-Maupome M, Schneider S. Prophylactic digoxin treatment reduces IL-17 production in vivo in the neonatal calf and moderates RSV-associated disease. PLoS One. 2019 Mar 25;14(3):e0214407. doi: 10.1371/journal.pone.0214407. PMID: 30908540; PMCID: PMC6433258.
1: Ehle M, Patel C, Giugliano RP. Digoxin: clinical highlights: a review of digoxin and its use in contemporary medicine. Crit Pathw Cardiol. 2011 Jun;10(2):93-8. doi: 10.1097/HPC.0b013e318221e7dd. Review. PubMed PMID: 21988950. 2: Felicilda-Reynaldo RF. Cardiac glycosides, digoxin toxicity, and the antidote. Medsurg Nurs. 2013 Jul-Aug;22(4):258-61. PubMed PMID: 24147325. 3: Huh JR, Leung MW, Huang P, Ryan DA, Krout MR, Malapaka RR, Chow J, Manel N, Ciofani M, Kim SV, Cuesta A, Santori FR, Lafaille JJ, Xu HE, Gin DY, Rastinejad F, Littman DR. Digoxin and its derivatives suppress TH17 cell differentiation by antagonizing RORγt activity. Nature. 2011 Apr 28;472(7344):486-90. doi: 10.1038/nature09978. Epub 2011 Mar 27. PubMed PMID: 21441909; PubMed Central PMCID: PMC3172133. 4: Yukawa M, Yukawa E, Suematsu F, Takiguchi T, Ikeda H, Aki H, Mimemoto M. Determination of digoxin clearance in Japanese elderly patients for optimization of drug therapy: a population pharmacokinetics analysis using nonlinear mixed-effects modelling. Drugs Aging. 2011 Oct 1;28(10):831-41. doi: 10.2165/11594230-000000000-00000. PubMed PMID: 21970310. 5: Cambridge D, Morgan CR, Allen G. Digoxin and digoxin derivative induced arrhythmias: in vitro binding and in vivo abolition of arrhythmias by digoxin immune Fab (DIGIBAND). Cardiovasc Res. 1992 Sep;26(9):906-11. PubMed PMID: 1451168. 6: Das G. Beta-methyl digoxin: a better absorbable digoxin. Int J Clin Pharmacol Ther Toxicol. 1989 Nov;27(11):521-5. Review. PubMed PMID: 2693372. 7: González-López J, Tutor JC. Diagnostic accuracy of a hyperbolic model in predicting digoxin concentrations based on glomerular filtration rates. Nefrologia. 2011;31(5):573-8. doi: 10.3265/Nefrologia.pre2011.Jul.10893. English, Spanish. PubMed PMID: 21959724. 8: Pouwels MJ, Hooymans PM, van der Aa GC, Gribnau FW. Comparison of steady-state serum concentrations of digoxin in tablets (Lanoxin) and capsules (Lanoxicaps) in the elderly. DICP. 1991 Oct;25(10):1043-6. PubMed PMID: 1803786. 9: Srinivas NR, Ramesh M. Digoxin - a therapeutic agent and mechanistic probe: review of liquid chromatographic mass spectrometric methods and recent nuances in the clinical pharmacology attributes of digoxin. Bioanalysis. 2009 Apr;1(1):97-113. doi: 10.4155/bio.09.14. Review. PubMed PMID: 21083191. 10: Anderson D, Penny R, O'Rourke MF. Anti-digoxin antibody in digoxin intoxication. Aust N Z J Med. 1981 Oct;11(5):480-3. PubMed PMID: 6173034. 11: Hedman A, Angelin B, Arvidsson A, Dahlqvist R. Digoxin-interactions in man: spironolactone reduces renal but not biliary digoxin clearance. Eur J Clin Pharmacol. 1992;42(5):481-5. PubMed PMID: 1606994. 12: Honda SA, Rios CN, Murakami L, Morita T, Scottolini AG, Bhagavan NV. Problems in determining levels of free digoxin in patients treated with digoxin immune FAb. J Clin Lab Anal. 1995;9(6):407-12. PubMed PMID: 8587010. 13: Marinow J, Olcay A, Schaumann W, Weiss W. Serum glycoside concentrations after single or repeated intravenous doses of beta-methyl-digoxin and digoxin. Eur J Clin Pharmacol. 1977 Mar 11;11(3):213-8. PubMed PMID: 856604. 14: Hess T, Bütler A, Stucki P. [Bioavailability of digoxin and beta-methyl-digoxin in patients with liver and gastro-intestinal diseases ]. Wien Klin Wochenschr. 1982 May 14;94(10):251-8. German. PubMed PMID: 7123952. 15: Butler VP Jr, Schmidt DH, Smith TW, Haber E, Raynor BD, Demartini P. Effects of sheep digoxin-specific antibodies and their Fab fragments on digoxin pharmacokinetics in dogs. J Clin Invest. 1977 Feb;59(2):345-59. PubMed PMID: 299860; PubMed Central PMCID: PMC333366. 16: Omidfar K, Kia S, Kashanian S, Paknejad M, Besharatie A, Kashanian S, Larijani B. Colloidal nanogold-based immunochromatographic strip test for the detection of digoxin toxicity. Appl Biochem Biotechnol. 2010 Mar;160(3):843-55. doi: 10.1007/s12010-009-8535-x. Epub 2009 Feb 18. PubMed PMID: 19224402. 17: Schwartz JB, Migliore PJ. Effect of nifedipine on serum digoxin concentration and renal digoxin clearance. Clin Pharmacol Ther. 1984 Jul;36(1):19-24. PubMed PMID: 6734045. 18: Miller JJ, Straub RW Jr, Valdes R Jr. Digoxin immunoassay with cross-reactivity of digoxin metabolites proportional to their biological activity. Clin Chem. 1994 Oct;40(10):1898-903. PubMed PMID: 7923769. 19: Grahame-Smith DG. Everest MS: Measurement of digoxin in plasma and its use in diagnosis of digoxin intoxication. Br Med J. 1969 Feb 1;1(5639):286-9. PubMed PMID: 5762647; PubMed Central PMCID: PMC1982164. 20: Panda S, Kar A. A novel phytochemical, digoxigenin-3-O-rutin in the amelioration of isoproterenol-induced myocardial infarction in rat: a comparison with digoxin. Cardiovasc Ther. 2012 Jun;30(3):125-35. doi: 10.1111/j.1755-5922.2010.00242.x. Epub 2010 Oct 20. PubMed PMID: 20961399.

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