Strophanthidin
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MedKoo CAT#: 463995

CAS#: 66-28-4

Description: Strophanthidin is a cardiotonic steroid that elevates the activity of Na+/K+-ATPase in cardiac myocytes. It decreases the potassium content and raises the sodium content in rabbit renal cortex slices.

Chemical Structure

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Strophanthidin
CAS# 66-28-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 463995
Name: Strophanthidin
CAS#: 66-28-4
Chemical Formula: C23H32O6
Exact Mass: 404.22
Molecular Weight: 404.500
Elemental Analysis: C, 68.29; H, 7.97; O, 23.73

Price and Availability

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250mg USD 550 2 Weeks
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Synonym: Strophanthidin; k-Strophanthidin; k Strophanthidin; Apocymarin; NSC 86078; NSC86078; NSC-86078;

IUPAC/Chemical Name: (3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-10H-cyclopenta[a]phenanthrene-10-carbaldehyde

InChi Key: ODJLBQGVINUMMR-HZXDTFASSA-N

InChi Code: InChI=1S/C23H32O6/c1-20-6-3-17-18(4-8-22(27)11-15(25)2-7-21(17,22)13-24)23(20,28)9-5-16(20)14-10-19(26)29-12-14/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3/t15-,16+,17-,18+,20+,21-,22-,23-/m0/s1

SMILES Code: C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=CC(OC4)=O)O)CC[C@@]5(C[C@H](CC[C@]35C=O)O)O

Appearance: Solid powder

Purity: >92% (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: To be determined

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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Strophanthidin is an inhibitor of N-acetyltransferase (IC50 = ~1.2 µM).
In vitro activity: Strophanthidin has potential as an anticancer agent. In A549 lung adenocarcinoma cells, strophanthidin was found to increase expression of TRAIL-R2, activating caspase 3/6/8 and inducing apoptosis by upregulating ACIN1 and LMNA. Strophanthidin also elevated Banf1 levels and downregulated p38 MAPK/ERK signaling, contributing to cell growth inhibition. Additionally, strophanthidin decreased collagen COL1A5 expression, affecting the cell microenvironment. Reference: Molecules. 2024 Feb 16;29(4):877. https://pubmed.ncbi.nlm.nih.gov/38398629/
In vivo activity: To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 404.50 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. Tian X, Gu L, Zeng F, Liu X, Zhou Y, Dou Y, Han J, Zhao Y, Zhang Y, Luo Q, Wang F. Strophanthidin Induces Apoptosis of Human Lung Adenocarcinoma Cells by Promoting TRAIL-DR5 Signaling. Molecules. 2024 Feb 16;29(4):877. doi: 10.3390/molecules29040877. PMID: 38398629; PMCID: PMC10892344. 2. Reddy D, Ghosh P, Kumavath R. Strophanthidin Attenuates MAPK, PI3K/AKT/mTOR, and Wnt/β-Catenin Signaling Pathways in Human Cancers. Front Oncol. 2020 Jan 17;9:1469. doi: 10.3389/fonc.2019.01469. PMID: 32010609; PMCID: PMC6978703.
In vitro protocol: 1. Tian X, Gu L, Zeng F, Liu X, Zhou Y, Dou Y, Han J, Zhao Y, Zhang Y, Luo Q, Wang F. Strophanthidin Induces Apoptosis of Human Lung Adenocarcinoma Cells by Promoting TRAIL-DR5 Signaling. Molecules. 2024 Feb 16;29(4):877. doi: 10.3390/molecules29040877. PMID: 38398629; PMCID: PMC10892344. 2. Reddy D, Ghosh P, Kumavath R. Strophanthidin Attenuates MAPK, PI3K/AKT/mTOR, and Wnt/β-Catenin Signaling Pathways in Human Cancers. Front Oncol. 2020 Jan 17;9:1469. doi: 10.3389/fonc.2019.01469. PMID: 32010609; PMCID: PMC6978703.
In vivo protocol: To be determined

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1: Shao LR, Janicot R, Stafstrom CE. Na+-K+-ATPase functions in the developing hippocampus: regional differences in CA1 and CA3 neuronal excitability and role in epileptiform network bursting. J Neurophysiol. 2021 Jan 1;125(1):1-11. doi: 10.1152/jn.00453.2020. Epub 2020 Nov 18. PMID: 33206576.

2: Mirzaei M, Züst T, Younkin GC, Hastings AP, Alani ML, Agrawal AA, Jander G. Less Is More: a Mutation in the Chemical Defense Pathway of Erysimum cheiranthoides (Brassicaceae) Reduces Total Cardenolide Abundance but Increases Resistance to Insect Herbivores. J Chem Ecol. 2020 Dec;46(11-12):1131-1143. doi: 10.1007/s10886-020-01225-y. Epub 2020 Nov 12. PMID: 33180277.

3: Shang XF, Miao XL, Dai LX, Guo X, Li B, Pan H, Zhang JY. The acaricidal mechanism and active compounds against Psoroptes cuniculi of the methanol extract of Adonis coerulea Maxim II: Integrated proteomics and SPR analysis. Vet Parasitol. 2020 Oct 15;287:109267. doi: 10.1016/j.vetpar.2020.109267. Epub ahead of print. PMID: 33091629.

4: Reddy D, Ghosh P, Kumavath R. Strophanthidin Attenuates MAPK, PI3K/AKT/mTOR, and Wnt/β-Catenin Signaling Pathways in Human Cancers. Front Oncol. 2020 Jan 17;9:1469. doi: 10.3389/fonc.2019.01469. PMID: 32010609; PMCID: PMC6978703.

5: Bai Y, Zhu W, Xu Y, Xie Z, Akihisa T, Manosroi J, Sun H, Feng F, Liu W, Zhang J. Characterization, quantitation, similarity evaluation and combination with Na+,K+-ATPase of cardiac glycosides from Streblus asper. Bioorg Chem. 2019 Jun;87:265-275. doi: 10.1016/j.bioorg.2019.03.049. Epub 2019 Mar 19. PMID: 30908969.

6: Karaś K, Sałkowska A, Walczak-Drzewiecka A, Ryba K, Dastych J, Bachorz RA, Ratajewski M. The cardenolides strophanthidin, digoxigenin and dihydroouabain act as activators of the human RORγ/RORγT receptors. Toxicol Lett. 2018 Oct 1;295:314-324. doi: 10.1016/j.toxlet.2018.07.002. Epub 2018 Jul 5. PMID: 29981919.

7: Laverdière I, Boileau M, Neumann AL, Frison H, Mitchell A, Ng SWK, Wang JCY, Minden MD, Eppert K. Leukemic stem cell signatures identify novel therapeutics targeting acute myeloid leukemia. Blood Cancer J. 2018 Jun 6;8(6):52. doi: 10.1038/s41408-018-0087-2. PMID: 29921955; PMCID: PMC6889502.

8: Pan L, Zhang Y, Zhao W, Zhou X, Wang C, Deng F. The cardiac glycoside oleandrin induces apoptosis in human colon cancer cells via the mitochondrial pathway. Cancer Chemother Pharmacol. 2017 Jul;80(1):91-100. doi: 10.1007/s00280-017-3337-2. Epub 2017 Jun 8. PMID: 28597038.

9: Wallner M, Khafaga M, Kolesnik E, Vafiadis A, Schwantzer G, Eaton DM, Curcic P, Köstenberger M, Knez I, Rainer PP, Pichler M, Pieske B, Lewinski DV. Istaroxime, a potential anticancer drug in prostate cancer, exerts beneficial functional effects in healthy and diseased human myocardium. Oncotarget. 2017 Jul 25;8(30):49264-49274. doi: 10.18632/oncotarget.17540. PMID: 28514771; PMCID: PMC5564766.

10: Kueh D, Barnett WH, Cymbalyuk GS, Calabrese RL. Na(+)/K(+) pump interacts with the h-current to control bursting activity in central pattern generator neurons of leeches. Elife. 2016 Sep 2;5:e19322. doi: 10.7554/eLife.19322. PMID: 27588351; PMCID: PMC5010386.

11: Knittel DN, Huber U, Stintzing FC, Kammerer DR. Effect of extraction, microbial fermentation and storage on the cardenolide profile of Strophanthus kombé Oliv. seed preparations. J Pharm Biomed Anal. 2016 Sep 10;129:96-104. doi: 10.1016/j.jpba.2016.06.036. Epub 2016 Jun 20. PMID: 27416523.

12: Hsiao PY, Lee SJ, Chen IS, Hsu HY, Chang HS. Cytotoxic cardenolides and sesquiterpenoids from the fruits of Reevesia formosana. Phytochemistry. 2016 Oct;130:282-90. doi: 10.1016/j.phytochem.2016.06.009. Epub 2016 Jul 4. PMID: 27386738.

13: Knittel DN, Lorenz P, Huber U, Stintzing FC, Kammerer DR. Characterization of the cardiac glycoside and lipid profiles of Strophanthus kombé Oliv. seeds. Z Naturforsch C J Biosci. 2016 Mar;71(3-4):55-64. doi: 10.1515/znc-2015-0186. PMID: 26974139.

14: Gozalpour E, Wilmer MJ, Bilos A, Masereeuw R, Russel FG, Koenderink JB. Heterogeneous transport of digitalis-like compounds by P-glycoprotein in vesicular and cellular assays. Toxicol In Vitro. 2016 Apr;32:138-45. doi: 10.1016/j.tiv.2015.12.009. Epub 2015 Dec 17. PMID: 26708294.

15: Swietach P, Spitzer KW, Vaughan-Jones RD. Na⁺ ions as spatial intracellular messengers for co-ordinating Ca²⁺ signals during pH heterogeneity in cardiomyocytes. Cardiovasc Res. 2015 Feb 1;105(2):171-81. doi: 10.1093/cvr/cvu251. Epub 2014 Dec 16. PMID: 25514933; PMCID: PMC4297422.

16: Carlier J, Guitton J, Romeuf L, Bévalot F, Boyer B, Fanton L, Gaillard Y. Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 15;975:65-76. doi: 10.1016/j.jchromb.2014.10.028. Epub 2014 Nov 1. PMID: 25438245.

17: Gozalpour E, Greupink R, Bilos A, Verweij V, van den Heuvel JJ, Masereeuw R, Russel FG, Koenderink JB. Convallatoxin: a new P-glycoprotein substrate. Eur J Pharmacol. 2014 Dec 5;744:18-27. doi: 10.1016/j.ejphar.2014.09.031. Epub 2014 Sep 28. PMID: 25264938.

18: Nagy N, Kormos A, Kohajda Z, Szebeni Á, Szepesi J, Pollesello P, Levijoki J, Acsai K, Virág L, Nánási PP, Papp JG, Varró A, Tóth A. Selective Na(+) /Ca(2+) exchanger inhibition prevents Ca(2+) overload-induced triggered arrhythmias. Br J Pharmacol. 2014 Dec;171(24):5665-81. doi: 10.1111/bph.12867. PMID: 25073832; PMCID: PMC4290709.

19: Füessl HS, Stiefelhagen P. Früher war das fast Gesetz. Warum werden Altere vor einer OP nicht mehr digitalisiert? [Formerly this was almost the rule. Why are the elderly no longer receiving digitalis before an operation?]. MMW Fortschr Med. 2014 Feb 6;156(2):17. German. PMID: 24934035.

20: Loh SH, Tsai YT, Lee CY, Chang CY, Tsai CS, Cheng TH, Lin CI. Antiarrhythmic effects of dehydroevodiamine in isolated human myocardium and cardiomyocytes. J Ethnopharmacol. 2014 May 14;153(3):753-62. doi: 10.1016/j.jep.2014.03.043. Epub 2014 Mar 27. PMID: 24680993.