Digitoxigenin
featured

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

Hodoodo CAT#: H562196

CAS#: 143-62-4

Description: Digitoxigenin is a precursor of cardiac glycosides. It acts by targeting the metastatic uveal melanoma gene signature.


Chemical Structure

img
Digitoxigenin
CAS# 143-62-4

Theoretical Analysis

Hodoodo Cat#: H562196
Name: Digitoxigenin
CAS#: 143-62-4
Chemical Formula: C23H34O4
Exact Mass: 374.25
Molecular Weight: 374.520
Elemental Analysis: C, 73.76; H, 9.15; O, 17.09

Price and Availability

Size Price Availability Quantity
10mg USD 275 2 weeks
25mg USD 550 2 weeks
50mg USD 950 2 weeks
Bulk inquiry

Synonym: Digitoxigenin; Cerberigenin; Thevetigenin; Echujetin; Digitoxigenine;

IUPAC/Chemical Name: 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-Dihydroxy-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 Key: XZTUSOXSLKTKJQ-CESUGQOBSA-N

InChi Code: InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1

SMILES Code: O=C1C=C([C@H]2CC[C@]3(O)[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]23C)CO1

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: >2 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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 374.52 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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Prisbe EJ, Verheyden JP, Montgomery WW, Strosberg AM. Digitoxigenin 3-O-beta- D-furanosides. J Med Chem. 1986 Feb;29(2):239-44. doi: 10.1021/jm00152a012. PMID: 3950906.


2: Sawlewicz L, Linde HH, Meyer K. 3-O-Phosphoryl-digitoxigenin [3-O-phosphoryl- digitoxigenin]. Helv Chim Acta. 1970;53(6):1382-5. German. doi: 10.1002/hlca.19700530618. PMID: 5471414.


3: Feng X, Wang C, Xu Y, Turley J, Xie Z, Pierre SV, Hao J. Topical Digitoxigenin for Wound Healing: A Feasibility Study. Bioengineering (Basel). 2018 Mar 5;5(1):21. doi: 10.3390/bioengineering5010021. PMID: 29510580; PMCID: PMC5874887.


4: Danieli N, Mazur Y, Sondheimer F. The synthesis of digitoxigenin. Tetrahedron. 1966 Sep;22(9):3189-93. doi: 10.1016/s0040-4020(01)82299-7. PMID: 5976053.


5: Schmoldt A, Benthe HF, Haberland G. Digitoxin metabolism by rat liver microsomes. Biochem Pharmacol. 1975 Sep 1;24(17):1639-41. PMID: 10.


6: Freitas CS, Oliveira-da-Silva JA, Lage DP, Costa RR, Mendonça DVC, Martins VT, Reis TAR, Antinarelli LMR, Machado AS, Tavares GSV, Ramos FF, Coelho VTS, Brito RCF, Ludolf F, Chávez-Fumagalli MA, Roatt BM, Ramos GS, Munkert J, Ottoni FM, Campana PRV, Humbert MV, Coimbra ES, Braga FC, Pádua RM, Coelho EAF. Digitoxigenin presents an effective and selective antileishmanial action against Leishmania infantum and is a potential therapeutic agent for visceral leishmaniasis. Parasitol Res. 2021 Jan;120(1):321-335. doi: 10.1007/s00436-020-06971-2. Epub 2020 Nov 16. PMID: 33191446; PMCID: PMC7667010.


7: Munkert J, Gomes ER, Marostica LL, Cota BB, Lopes CLM, Andrade SF, Filho JDS, Alves RJ, Oliveira MC, Braga FC, Simões CMO, Pádua RM, de Barros ALB. New 99mTc-Labeled Digitoxigenin Derivative for Cancer Cell Identification. ACS Omega. 2019 Dec 11;4(26):22048-22056. doi: 10.1021/acsomega.9b03167. PMID: 31891085; PMCID: PMC6933791.


8: Wang H, Zhang H, Fan K, Zhang D, Hu A, Zeng X, Liu YL, Tan G, Wang H. Frugoside delays osteoarthritis progression via inhibiting miR-155-modulated synovial macrophage M1 polarization. Rheumatology (Oxford). 2021 Oct 2;60(10):4899-4909. doi: 10.1093/rheumatology/keab018. PMID: 33493345.


9: Erlenkamp S, Gretzer B, Zillikens S, Glitsch HG, Pusch H, Staroske T, Welzel P. Na+/K+ pump inhibition and positive inotropic effect of digitoxigenin and some C-22-substituted derivatives in sheep cardiac preparations. Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):54-62. doi: 10.1007/pl00005138. PMID: 9459573.


10: Cartaud A, Marcher K, Ozon R. Digitoxigenin, a digitalis steroid, induces meiotic maturation of Xenopus laevis oocytes. J Steroid Biochem. 1984 Jul;21(1):101-6. doi: 10.1016/0022-4731(84)90066-9. PMID: 6087028.


11: Valadares JMM, Bajaj SO, Li H, Wang HL, Silva SC, Garcia IJP, Pereira DG, Azalim P, Quintas LEM, Noël F, Cortes VF, O'Doherty GA, Barbosa LA. Cytotoxic effect of carbohydrate derivatives of digitoxigenin involves modulation of plasma membrane Ca2+ -ATPase. J Cell Biochem. 2021 Dec;122(12):1903-1914. doi: 10.1002/jcb.30150. Epub 2021 Sep 22. PMID: 34553411; PMCID: PMC8671332.


12: Ramirez M, Del Valle L, Sanchez-Mendoza A, Tenorio FA, Zarco G, Pastelin G. Effect of the digitoxigenin derivative, INCICH-D7, on Na+, K+-ATPase. Biochem Pharmacol. 2005 Sep 15;70(6):851-7. doi: 10.1016/j.bcp.2005.06.020. PMID: 16081050.


13: JELLIFFE RW, BLANKENHORN DH. GAS CHROMATOGRAPHY OF DIGITOXIGENIN AND DIGOXIGENIN. J Chromatogr. 1963 Oct;12:268-70. doi: 10.1016/s0021-9673(01)83686-4. PMID: 14071804.


14: Boff L, Munkert J, Ottoni FM, Zanchett Schneider NF, Ramos GS, Kreis W, Fernandes de Andrade S, Dias de Souza Filho J, Braga FC, Alves RJ, Maia de Pádua R, Oliveira Simões CM. Potential anti-herpes and cytotoxic action of novel semisynthetic digitoxigenin-derivatives. Eur J Med Chem. 2019 Apr 1;167:546-561. doi: 10.1016/j.ejmech.2019.01.076. Epub 2019 Feb 2. PMID: 30798081.


15: Peng Q, Li H, Chen J, Wang Y, Tang Z. Oral submucous fibrosis in Asian countries. J Oral Pathol Med. 2020 Apr;49(4):294-304. doi: 10.1111/jop.12924. Epub 2019 Jul 16. PMID: 31310693.


16: Altman PM, Einstein R, Goodman AH, Thomas RE. Inotropic activity of digitoxigenin glucoside and related glycosides. Arzneimittelforschung. 1988 Aug;38(8):1115-9. PMID: 3196405.


17: Kawaguchi K, Koike S, Hirotani M, Fujihara M, Furuya T, Iwata R, Morimoto K. Biotransformation of digitoxigenin by cultured Strophanthus hybrid cells. Phytochemistry. 1998 Apr;47(7):1261-5. doi: 10.1016/s0031-9422(97)00748-6. PMID: 9611827.


18: Boff L, Persich L, Brambila P, Ottoni FM, Munkert J, Ramos GS, Soares Viana AR, Kreis W, Braga FC, Alves RJ, Maia de Pádua R, Schneider NFZ, Oliveira Simões CM. Investigation of the cytotoxic activity of two novel digitoxigenin analogues on H460 lung cancer cells. Anticancer Drugs. 2020 Jun;31(5):452-462. doi: 10.1097/CAD.0000000000000872. PMID: 32079825.


19: Wang HY, Qi Z, Wu B, Kang SW, Rojanasakul Y, O'Doherty GA. C5'-Alkyl Substitution Effects on Digitoxigenin α-l-Glycoside Cancer Cytotoxicity. ACS Med Chem Lett. 2011 Apr 14;2(4):259-263. doi: 10.1021/ml100291n. PMID: 21572583; PMCID: PMC3092485.


20: Feng X, Turley J, Xie Z, Pierre SV, Koc H, Khan MO, Hao J. An LC-MS/MS method for the determination of digitoxigenin in skin samples and its application to skin permeation and metabolic stability studies. J Pharm Biomed Anal. 2017 May 10;138:378-385. doi: 10.1016/j.jpba.2016.12.029. Epub 2016 Dec 23. PMID: 28139268.