Digitoxin | CAS#71-63-6 | cardiac glycoside

MedKoo Cat#: 598263 | Name: Digitoxin

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Description:

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

Digitoxin is a cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting.

Chemical Structure

Digitoxin

CAS#71-63-6

Theoretical Analysis

MedKoo Cat#: 598263

Name: Digitoxin

CAS#: 71-63-6

Chemical Formula: C41H64O13

Exact Mass: 764.4347

Molecular Weight: 764.95

Elemental Analysis: C, 64.38; H, 8.43; O, 27.19

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
500mg	USD 750.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Synonym

Digitoxin; Digitoxoside; Lanatoxin; Carditalin; NSC 7529; NSC-7529; NSC7529;

IUPAC/Chemical Name

4-((3S,5R,8R,9S,10S,13R,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)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one

InChi Key

WDJUZGPOPHTGOT-XUDUSOBPSA-N

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

SMILES Code

C[C@@H]1[C@@H](O)[C@@H](O)C[C@H](O[C@@H]2[C@@H](C)O[C@@H](O[C@@H]3[C@@H](C)O[C@@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@@]7(C)[C@]6(O)CC[C@@H]7C8=CC(OC8)=O)C4)C[C@@H]3O)C[C@@H]2O)O1

Appearance

Solid powder

Purity

>98% (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:

Digitoxin is an effective Na+/K+-ATPase inhibitor, the EC50 value of Digitoxin is 0.78 μM.

In vitro activity:

Subsequently, the anti-HCC effect of digitoxin on HepG2/ADM cells was assessed using the MTT assay. As shown in Fig. 1C, digitoxin decreased the viability of HepG2/ADM cells in a dose-dependent manner, with IC50 values of 132.65±33.83, 52.29±6.26 and 9.13±3.67 nM following treatment for 24, 48 and 72 h, respectively. Reference: Oncol Lett. 2020 Oct;20(4):71. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7436926/

In vivo activity:

The dose range of digitoxin, 0-30 μg/100g cotton rat, was calculated to approximate the human dose routinely used to treat heart failure (0.1 mg digitoxin, Merck KGaA, Darmstadt, Germany). As shown in Figure 1 and summarized in Table I, significant digitoxin-dependent reductions were found at >10 μg doses for 5 of the 7 cytokines. The digitoxin-dependent reductions were specific and saturating for each cytokine, but did not reduce any of them to zero. Reference: In Vivo. 2020 Nov-Dec; 34(6): 3723–3730. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7811644/

	Solvent	mg/mL	mM
Solubility
	DMSO	60.0	78.44
	DMF	25.0	32.68
	DMF:PBS (pH 7.2) (1:1)	0.5	0.65
	Ethanol	5.0	6.54

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 764.95 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.

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. Lei Y, Gan H, Huang Y, Chen Y, Chen L, Shan A, Zhao H, Wu M, Li X, Ma Q, Wang J, Zhang E, Zhang J, Li Y, Xue F, Deng L. Digitoxin inhibits proliferation of multidrug-resistant HepG2 cells through G2/M cell cycle arrest and apoptosis. Oncol Lett. 2020 Oct;20(4):71. doi: 10.3892/ol.2020.11932. Epub 2020 Jul 30. PMID: 32863904; PMCID: PMC7436926. 2. Schinner C, Olivares-Florez S, Schlipp A, Trenz S, Feinendegen M, Flaswinkel H, Kempf E, Egu DT, Yeruva S, Waschke J. The inotropic agent digitoxin strengthens desmosomal adhesion in cardiac myocytes in an ERK1/2-dependent manner. Basic Res Cardiol. 2020 Jun 17;115(4):46. doi: 10.1007/s00395-020-0805-3. PMID: 32556797; PMCID: PMC7299919. 3. Pollard BS, BLANCOl JC, Pollard JR. Classical Drug Digitoxin Inhibits Influenza Cytokine Storm, With Implications for Covid-19 Therapy. In Vivo. 2020 Nov-Dec;34(6):3723-3730. doi: 10.21873/invivo.12221. PMID: 33144490; PMCID: PMC7811644. 4. Gan H, Qi M, Chan C, Leung P, Ye G, Lei Y, Liu A, Xue F, Liu D, Ye W, Zhang D, Deng L, Chen J. Digitoxin inhibits HeLa cell growth through the induction of G2/M cell cycle arrest and apoptosis in vitro and in vivo. Int J Oncol. 2020 Aug;57(2):562-573. doi: 10.3892/ijo.2020.5070. Epub 2020 May 25. PMID: 32468057.

In vitro protocol:

In vivo protocol:

1. Pollard BS, BLANCOl JC, Pollard JR. Classical Drug Digitoxin Inhibits Influenza Cytokine Storm, With Implications for Covid-19 Therapy. In Vivo. 2020 Nov-Dec;34(6):3723-3730. doi: 10.21873/invivo.12221. PMID: 33144490; PMCID: PMC7811644. 2. Gan H, Qi M, Chan C, Leung P, Ye G, Lei Y, Liu A, Xue F, Liu D, Ye W, Zhang D, Deng L, Chen J. Digitoxin inhibits HeLa cell growth through the induction of G2/M cell cycle arrest and apoptosis in vitro and in vivo. Int J Oncol. 2020 Aug;57(2):562-573. doi: 10.3892/ijo.2020.5070. Epub 2020 May 25. PMID: 32468057.

1: Pongrakhananon V, Stueckle TA, Wang HL, O'Doherty GA, Dinu CZ, Chanvorachote P, Rojanasakul Y. Monosaccharide digitoxin derivative sensitize human non-small cell lung cancer cells to anoikis through Mcl-1 proteasomal degradation. Biochem Pharmacol. 2014 Mar 1;88(1):23-35. doi: 10.1016/j.bcp.2013.10.027. Epub 2013 Nov 11. PubMed PMID: 24231508; PubMed Central PMCID: PMC3970117. 2: Bylda C, Thiele R, Kobold U, Volmer DA. Simultaneous quantification of digoxin, digitoxin, and their metabolites in serum using high performance liquid chromatography-tandem mass spectrometry. Drug Test Anal. 2015 Oct;7(10):937-46. doi: 10.1002/dta.1781. Epub 2015 Mar 4. PubMed PMID: 25735870. 3: Baryal KN, Adhikari S, Zhu J. Catalytic stereoselective synthesis of β-digitoxosides: direct synthesis of digitoxin and C1'-epi-digitoxin. J Org Chem. 2013 Dec 20;78(24):12469-76. doi: 10.1021/jo4021419. Epub 2013 Dec 11. PubMed PMID: 24295510. 4: Bylda C, Thiele R, Kobold U, Bujotzek A, Volmer DA. Rapid quantification of digitoxin and its metabolites using differential ion mobility spectrometry-tandem mass spectrometry. Anal Chem. 2015 Feb 17;87(4):2121-8. doi: 10.1021/ac503187z. Epub 2015 Jan 26. PubMed PMID: 25588102. 5: Elbaz HA, Stueckle TA, Wang HY, O'Doherty GA, Lowry DT, Sargent LM, Wang L, Dinu CZ, Rojanasakul Y. Digitoxin and a synthetic monosaccharide analog inhibit cell viability in lung cancer cells. Toxicol Appl Pharmacol. 2012 Jan 1;258(1):51-60. doi: 10.1016/j.taap.2011.10.007. Epub 2011 Oct 18. PubMed PMID: 22037315; PubMed Central PMCID: PMC3254807. 6: Beale TM, Taylor MS. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org Lett. 2013 Mar 15;15(6):1358-61. doi: 10.1021/ol4003042. Epub 2013 Mar 6. PubMed PMID: 23465047. 7: Castello LM, Negro S, Santi F, Zanotti I, Vidali M, Bagnati M, Bellomo G, Avanzi GC. Accidental digitoxin intoxication: an interplay between laboratory and clinical medicine. Biochem Med (Zagreb). 2012;22(3):380-4. PubMed PMID: 23092069; PubMed Central PMCID: PMC3900044. 8: Schmoldt A, Benthe HF, Haberland G. Digitoxin metabolism by rat liver microsomes. Biochem Pharmacol. 1975 Sep 1;24(17):1639-41. PubMed PMID: 10; PubMed Central PMCID: PMC5922622. 9: Ma Y, Li Z, Shi H, Zhang J, Yu B. Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates. J Org Chem. 2011 Dec 2;76(23):9748-56. doi: 10.1021/jo201850z. Epub 2011 Nov 4. PubMed PMID: 22054226. 10: Caldwell JH, Greenberger NJ. Interruption of the enterohepatic circulation of digitoxin by cholestyramine. I. Protection against lethal digitoxin intoxication. J Clin Invest. 1971 Dec;50(12):2626-37. PubMed PMID: 5129314; PubMed Central PMCID: PMC292212. 11: Arlotto MP, Sonderfan AJ, McKinney MM, Parkinson A. Digitoxin metabolism by liver microsomal cytochrome P-450 and UDP-glucuronosyltransferase and its role in the protection of rats from digitoxin toxicity by pregnenolone-16 alpha-carbonitrile. Arch Biochem Biophys. 1986 Nov 15;251(1):188-97. PubMed PMID: 3098175. 12: Datta P, Dasgupta A. Interference from digitoxin-like immunoreactive factors reduced in a new monoclonal chemiluminescent digitoxin assay. Ther Drug Monit. 1998 Dec;20(6):663-8. PubMed PMID: 9853984. 13: Haux J, Klepp O, Spigset O, Tretli S. Digitoxin medication and cancer; case control and internal dose-response studies. BMC Cancer. 2001;1:11. Epub 2001 Aug 10. PubMed PMID: 11532201; PubMed Central PMCID: PMC48150. 14: Caldwell JH, Bush CA, Greenberger NJ. Interruption of the enterohepatic circulation of digitoxin by cholestyramine. II. Effect on metabolic disposition of tritium-labeled digitoxin and cardiac systolic intervals in man. J Clin Invest. 1971 Dec;50(12):2638-44. PubMed PMID: 5129315; PubMed Central PMCID: PMC292213. 15: Storstein L. Studies on digitalis. XI. Digitoxin metabolism in patients with impaired renal function. Clin Pharmacol Ther. 1977 May;21(5):536-46. PubMed PMID: 858212. 16: Sphakianaki E, Tsouderos I, Morali A, Kokkas B, Papadopoulos K, Kotoula M, Paradelis A. Interactions between digitoxin and some antiarrhythmic drugs. Methods Find Exp Clin Pharmacol. 1992 Jun;14(5):355-60. PubMed PMID: 1513190. 17: Wood WG, Färber P, Kurowski V. A case of divergent digitoxin values under treatment of a patient with acute digitoxin overdose with digitalis antibody fragments. Klin Wochenschr. 1990 Mar 16;68(6):324-7. PubMed PMID: 2335903. 18: Takahashi M, Sada T, Taneichi Y, Okabe F, Ito Y, Morishima A. Some observations on serum concentrations of digitoxin and digoxin. Jpn Heart J. 1979 Sep;20(5):623-9. PubMed PMID: 501928. 19: Nolte E, Sobel A, Wach S, Hertlein H, Ebert N, Müller-Uri F, Slany R, Taubert H, Wullich B, Kreis W. The New Semisynthetic Cardenolide Analog 3β-[2-(1-Amantadine)-1-on-ethylamine]-digitoxigenin (AMANTADIG) Efficiently Suppresses Cell Growth in Human Leukemia and Urological Tumor Cell Lines. Anticancer Res. 2015 Oct;35(10):5271-5. PubMed PMID: 26408686. 20: Vöhringer HF, Rietbrock N. Digitalis therapy in renal failure with special regard to digitoxin. Int J Clin Pharmacol Ther Toxicol. 1981 Apr;19(4):175-84. Review. PubMed PMID: 7021432.