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

MedKoo CAT#: 406545

CAS#: 53003-10-4

Description: Salinomycin is an antibacterial and coccidiostat ionophore therapeutic drug. Salinomycin has been shown by Piyush Gupta et al. of the Massachusetts Institute of Technology and the Broad Institute to kill breast cancer stem cells in mice at least 100 times more effectively than the anti-cancer drug paclitaxel. The mechanism of action by which salinomycin kills cancer stem cells specifically remains unknown, but is thought to be due to its action as a potassium ionophore. Salinomycin could induce apoptosis of human cancer cells. Promising results from a few clinical pilote studies reveal that salinomycin is able to effectively eliminate CSCs and to induce partial clinical regression of heavily pretreated and therapy-resistant cancers.

Chemical Structure

CAS# 53003-10-4

Theoretical Analysis

MedKoo Cat#: 406545
Name: Salinomycin
CAS#: 53003-10-4
Chemical Formula: C42H69NaO11
Exact Mass: 750.49181
Molecular Weight: 772.98
Elemental Analysis: C, 67.17; H, 9.39; O, 23.43

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Synonym: AHR 3096; AHR3096; AHR-3096; HSDB 7032; HSDB7032; HSDB-7032; K 364; Salinomycin; BioCox; Sacox; Salocin; Coxistac.

IUPAC/Chemical Name: (R)-2-((2R,5S,6R)-6-((2S,3S,4S,6R)-6-((2S,5S,7R,9S,10S,12R,15R)-2-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[]pentadec-13-en-9-yl)-3-hydroxy-4-methyl-5-oxooctan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)butanoic acid


InChi Code: InChI=1S/C42H70O11/c1-11-29(38(46)47)31-15-14-23(4)36(50-31)27(8)34(44)26(7)35(45)30(12-2)37-24(5)22-25(6)41(51-37)19-16-32(43)42(53-41)21-20-39(10,52-42)33-17-18-40(48,13-3)28(9)49-33/h16,19,23-34,36-37,43-44,48H,11-15,17-18,20-22H2,1-10H3,(H,46,47)/t23-,24-,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,36+,37-,39-,40+,41-,42-/m0/s1

SMILES Code: CC[C@@H](C(O)=O)[C@H]1CC[C@@H]([C@H]([C@H]([C@@H]([C@@H](C([C@@H]([C@H]2O[C@]3([C@@H](C[C@@H]2C)C)O[C@]4([C@@H](C=C3)O)CC[C@](O4)([C@H]5CC[C@](CC)([C@@H](O5)C)O)C)CC)=O)C)O)C)O1)C

Appearance: brown solid powder

Purity: >20 % (feed grade)

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, not in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 772.98 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.

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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

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1: Zhao P, Dong S, Bhattacharyya J, Chen M. iTEP Nanoparticle-Delivered Salinomycin Displays an Enhanced Toxicity to Cancer Stem Cells in Orthotopic Breast Tumors. Mol Pharm. 2014 Aug 4;11(8):2703-12. doi: 10.1021/mp5002312. Epub 2014 Jul 1. PubMed PMID: 24960465.

2: Lu W, Li Y. Salinomycin suppresses LRP6 expression and inhibits both Wnt/β-catenin and mTORC1 signaling in breast and prostate cancer cells. J Cell Biochem. 2014 Jun 6. doi: 10.1002/jcb.24850. [Epub ahead of print] PubMed PMID: 24905570.

3: Huang X, Borgström B, Månsson L, Persson L, Oredsson S, Hegardt C, Strand D. Semisynthesis of SY-1 for Investigation of Breast Cancer Stem Cell Selectivity of C-Ring-Modified Salinomycin Analogues. ACS Chem Biol. 2014 Jul 18;9(7):1587-94. doi: 10.1021/cb5002153. Epub 2014 May 29. PubMed PMID: 24841425.

4: Klose J, Stankov MV, Kleine M, Ramackers W, Panayotova-Dimitrova D, Jäger MD, Klempnauer J, Winkler M, Bektas H, Behrens GM, Vondran FW. Inhibition of autophagic flux by salinomycin results in anti-cancer effect in hepatocellular carcinoma cells. PLoS One. 2014 May 9;9(5):e95970. doi: 10.1371/journal.pone.0095970. eCollection 2014. PubMed PMID: 24816744; PubMed Central PMCID: PMC4015957.

5: Boehmerle W, Muenzfeld H, Springer A, Huehnchen P, Endres M. Specific targeting of neurotoxic side effects and pharmacological profile of the novel cancer stem cell drug salinomycin in mice. J Mol Med (Berl). 2014 Aug;92(8):889-900. doi: 10.1007/s00109-014-1155-0. Epub 2014 Apr 27. PubMed PMID: 24770997.

6: Calzolari A, Saulle E, De Angelis ML, Pasquini L, Boe A, Pelacchi F, Ricci-Vitiani L, Baiocchi M, Testa U. Salinomycin potentiates the cytotoxic effects of TRAIL on glioblastoma cell lines. PLoS One. 2014 Apr 16;9(4):e94438. doi: 10.1371/journal.pone.0094438. eCollection 2014. PubMed PMID: 24740347; PubMed Central PMCID: PMC3989199.

7: Bissinger R, Malik A, Jilani K, Lang F. Triggering of Erythrocyte Cell Membrane Scrambling by Salinomycin. Basic Clin Pharmacol Toxicol. 2014 Apr 10. doi: 10.1111/bcpt.12250. [Epub ahead of print] PubMed PMID: 24717091.

8: Antoszczak M, Maj E, Stefańska J, Wietrzyk J, Janczak J, Brzezinski B, Huczyński A. Synthesis, antiproliferative and antibacterial activity of new amides of salinomycin. Bioorg Med Chem Lett. 2014 Apr 1;24(7):1724-9. doi: 10.1016/j.bmcl.2014.02.042. Epub 2014 Feb 25. PubMed PMID: 24631190.

9: Antoszczak M, Popiel K, Stefańska J, Wietrzyk J, Maj E, Janczak J, Michalska G, Brzezinski B, Huczyński A. Synthesis, cytotoxicity and antibacterial activity of new esters of polyether antibiotic - salinomycin. Eur J Med Chem. 2014 Apr 9;76:435-44. doi: 10.1016/j.ejmech.2014.02.031. Epub 2014 Feb 14. PubMed PMID: 24602789.

10: Mao J, Fan S, Ma W, Fan P, Wang B, Zhang J, Wang H, Tang B, Zhang Q, Yu X, Wang L, Song B, Li L. Roles of Wnt/β-catenin signaling in the gastric cancer stem cells proliferation and salinomycin treatment. Cell Death Dis. 2014 Jan 30;5:e1039. doi: 10.1038/cddis.2013.515. PubMed PMID: 24481453; PubMed Central PMCID: PMC4040703.

11: Kopp F, Hermawan A, Oak PS, Herrmann A, Wagner E, Roidl A. Salinomycin treatment reduces metastatic tumor burden by hampering cancer cell migration. Mol Cancer. 2014 Jan 27;13:16. doi: 10.1186/1476-4598-13-16. PubMed PMID: 24468090; PubMed Central PMCID: PMC3909296.

12: Zhu LQ, Zhen YF, Zhang Y, Guo ZX, Dai J, Wang XD. Salinomycin activates AMP-activated protein kinase-dependent autophagy in cultured osteoblastoma cells: a negative regulator against cell apoptosis. PLoS One. 2013 Dec 17;8(12):e84175. doi: 10.1371/journal.pone.0084175. eCollection 2013. PubMed PMID: 24358342; PubMed Central PMCID: PMC3866127.

13: Booth L, Roberts JL, Conley A, Cruickshanks N, Ridder T, Grant S, Poklepovic A, Dent P. HDAC inhibitors enhance the lethality of low dose salinomycin in parental and stem-like GBM cells. Cancer Biol Ther. 2014 Mar 1;15(3):305-16. doi: 10.4161/cbt.27309. Epub 2013 Dec 18. PubMed PMID: 24351423; PubMed Central PMCID: PMC3974832.

14: Wu D, Zhang Y, Huang J, Fan Z, Shi F, Wang S. Salinomycin inhibits proliferation and induces apoptosis of human nasopharyngeal carcinoma cell in vitro and suppresses tumor growth in vivo. Biochem Biophys Res Commun. 2014 Jan 10;443(2):712-7. doi: 10.1016/j.bbrc.2013.12.032. Epub 2013 Dec 12. PubMed PMID: 24333874.

15: Liffers ST, Tilkorn DJ, Stricker I, Junge CG, Al-Benna S, Vogt M, Verdoodt B, Steinau HU, Tannapfel A, Tischoff I, Mirmohammadsadegh A. Salinomycin increases chemosensitivity to the effects of doxorubicin in soft tissue sarcomas. BMC Cancer. 2013 Oct 21;13:490. doi: 10.1186/1471-2407-13-490. PubMed PMID: 24144362; PubMed Central PMCID: PMC3854645.

16: Borgström B, Huang X, Pošta M, Hegardt C, Oredsson S, Strand D. Synthetic modification of salinomycin: selective O-acylation and biological evaluation. Chem Commun (Camb). 2013 Nov 4;49(85):9944-6. doi: 10.1039/c3cc45983g. PubMed PMID: 24037337.

17: Kim JH, Choi AR, Kim YK, Kim HS, Yoon S. Low amount of salinomycin greatly increases Akt activation, but reduces activated p70S6K levels. Int J Mol Sci. 2013 Aug 22;14(9):17304-18. doi: 10.3390/ijms140917304. PubMed PMID: 23975168; PubMed Central PMCID: PMC3794729.

18: Zhou S, Wang F, Wong ET, Fonkem E, Hsieh TC, Wu JM, Wu E. Salinomycin: a novel anti-cancer agent with known anti-coccidial activities. Curr Med Chem. 2013;20(33):4095-101. Review. PubMed PMID: 23931281; PubMed Central PMCID: PMC4102832.

19: Zhou J, Li P, Xue X, He S, Kuang Y, Zhao H, Chen S, Zhi Q, Guo X. Salinomycin induces apoptosis in cisplatin-resistant colorectal cancer cells by accumulation of reactive oxygen species. Toxicol Lett. 2013 Oct 24;222(2):139-45. doi: 10.1016/j.toxlet.2013.07.022. Epub 2013 Aug 2. PubMed PMID: 23916687.

20: Ojo OO, Bhadauria S, Rath SK. Dose-dependent adverse effects of salinomycin on male reproductive organs and fertility in mice. PLoS One. 2013 Jul 1;8(7):e69086. doi: 10.1371/journal.pone.0069086. Print 2013. PubMed PMID: 23840907; PubMed Central PMCID: PMC3698082.

Additional Information

  The ability of salinomycin to kill both CSCs and therapy-resistant cancer cells may define the compound as a novel and an effective anticancer drug. It has been also shown that Salinomycin and its derivatives exhibit potent antiproliferative activity against the drug-resistant cancer cell lines.