Disodium cantharidin (salt) | CAS# 1465-77-6 (salt) | inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A)

MedKoo Cat#: 412267 | Name: Cantharidin sodium

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Description:

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

Disodium cantharidin is a toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally. Inhibits type 1 and type 2A protein phosphatase; cantharidine is the 2,3-dicarboxylic anhydride. Diluted solutions of cantharidin can be used as a topical medication to remove warts and tattoos and to treat the small papules of molluscum contagiosum.

Chemical Structure

Cantharidin sodium

CAS#1465-77-6 (sodium)

Theoretical Analysis

MedKoo Cat#: 412267

Name: Cantharidin sodium

CAS#: 1465-77-6 (sodium)

Chemical Formula: C10H12Na2O5

Exact Mass: 258.0480

Molecular Weight: 258.18

Elemental Analysis: C, 46.52; H, 4.69; Na, 17.81; O, 30.98

Price and Availability

Size	Price	Availability
10mg	USD 450.00	2 Weeks
25mg	USD 750.00	2 Weeks
50mg	USD 1,450.00	2 Weeks

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Related CAS #

56-25-7 (lactone) 76970-77-9 (imide) 1465-77-6 (sodium)

Synonym

Disodium cantharidin; Cantharidin disodium; Disodium cantharidate; Disodium cantharidinate; Sodium cantharidate;

IUPAC/Chemical Name

disodium;(1S,2R,3S,4R)-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylate

InChi Key

JFALSOLNDKMHAL-UHFFFAOYSA-L

InChi Code

InChI=1S/C10H14O5.2Na/c1-9(7(11)12)5-3-4-6(15-5)10(9,2)8(13)14;;/h5-6H,3-4H2,1-2H3,(H,11,12)(H,13,14);;/q;2*+1/p-2

SMILES Code

C[C@]1([C@H]2CC[C@@H]([C@]1(C)C(=O)[O-])O2)C(=O)[O-].[Na+].[Na+]

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

A protein phosphatase inhibitor.

In vitro activity:

The growth of HepG2 and SMMC-7721 cells was significantly inhibited by cantharidin stimulation for 48 h. The growth inhibition rates of HepG2 and SMMC-7721 cells increased with the increase of cantharidin concentration (Figures 1(a) and 1(b)). Apoptosis was further detected by the TUNEL assay. The results showed that the apoptosis rate of SMMC-7721 cells increased after cantharidin treatment (Figures 1(c) and 1(d)). Reference: Evid Based Complement Alternat Med. 2022 Jul 11;2022:2197071. https://pubmed.ncbi.nlm.nih.gov/35860003/

In vivo activity:

Cantharidin was found to significantly inhibit osteosarcoma lesion in the tibia of nude mice detected by X-ray (Fig. 7C); xenograft-bearing legs in the control group showed significant invasive tumors which damaged the bone marrow barrier and caused the bone destruction; however, the xenograft-bearing legs of the cantharidin treated mice showed less architecture destruction with limited tumors and intact bone infrastructure. Reference: Int J Biol Sci. 2021 Jun 16;17(10):2504-2522. https://pubmed.ncbi.nlm.nih.gov/34326690/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	2.0	7.75

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 258.18 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. Wei C, Deng X, Gao S, Wan X, Chen J. Cantharidin Inhibits Proliferation of Liver Cancer by Inducing DNA Damage via KDM4A-Dependent Histone H3K36 Demethylation. Evid Based Complement Alternat Med. 2022 Jul 11;2022:2197071. doi: 10.1155/2022/2197071. PMID: 35860003; PMCID: PMC9293552. 2. Swagatika S, Tomar RS. Cantharidin downregulates PSD1 expression and inhibits autophagic flux in yeast cells. FEBS Open Bio. 2022 May;12(5):1017-1035. doi: 10.1002/2211-5463.13196. Epub 2022 Mar 29. PMID: 33999504; PMCID: PMC9063437. 3. Hu S, Chang J, Ruan H, Zhi W, Wang X, Zhao F, Ma X, Sun X, Liang Q, Xu H, Wang Y, Yang Y. Cantharidin inhibits osteosarcoma proliferation and metastasis by directly targeting miR-214-3p/DKK3 axis to inactivate β-catenin nuclear translocation and LEF1 translation. Int J Biol Sci. 2021 Jun 16;17(10):2504-2522. doi: 10.7150/ijbs.51638. PMID: 34326690; PMCID: PMC8315017. 4. Huang X, Tang W, Lin C, Sa Z, Xu M, Liu J, Wang L, Li W, Chen Y, Yang C. Protective mechanism of Astragalus Polysaccharides against Cantharidin-induced liver injury determined in vivo by liquid chromatography/mass spectrometry metabolomics. Basic Clin Pharmacol Toxicol. 2021 Jul;129(1):61-71. doi: 10.1111/bcpt.13585. Epub 2021 Apr 22. PMID: 33834601.

In vitro protocol:

In vivo protocol:

1. Hu S, Chang J, Ruan H, Zhi W, Wang X, Zhao F, Ma X, Sun X, Liang Q, Xu H, Wang Y, Yang Y. Cantharidin inhibits osteosarcoma proliferation and metastasis by directly targeting miR-214-3p/DKK3 axis to inactivate β-catenin nuclear translocation and LEF1 translation. Int J Biol Sci. 2021 Jun 16;17(10):2504-2522. doi: 10.7150/ijbs.51638. PMID: 34326690; PMCID: PMC8315017. 2. Huang X, Tang W, Lin C, Sa Z, Xu M, Liu J, Wang L, Li W, Chen Y, Yang C. Protective mechanism of Astragalus Polysaccharides against Cantharidin-induced liver injury determined in vivo by liquid chromatography/mass spectrometry metabolomics. Basic Clin Pharmacol Toxicol. 2021 Jul;129(1):61-71. doi: 10.1111/bcpt.13585. Epub 2021 Apr 22. PMID: 33834601.

1: Ren Y, Zhang SW, Xie ZH, Xu XM, Chen LL, Lou ZG, Weng GB, Yao XP. Cantharidin induces G2/M arrest and triggers apoptosis in renal cell carcinoma. Mol Med Rep. 2016 Dec;14(6):5614-5618. doi: 10.3892/mmr.2016.5963. Epub 2016 Nov 23. PubMed PMID: 27878266. 2: Lü S, Jiang M, Huo T, Li X, Zhang Y. 3-hydroxy-3-methyl glutaryl coenzyme A reductase: an essential actor in the biosynthesis of cantharidin in the blister beetle Epicauta chinensis Laporte. Insect Mol Biol. 2016 Feb;25(1):58-71. doi: 10.1111/imb.12198. Epub 2015 Nov 14. PubMed PMID: 26566751. 3: Zhou CJ, Qiao LM, Zhao LH, Li ZY. Evaluation of the impact of cantharidin on rat CYP enzymes by using a cocktail of probe drugs. Fitoterapia. 2015 Dec;107:49-53. doi: 10.1016/j.fitote.2015.10.008. Epub 2015 Oct 22. PubMed PMID: 26498206. 4: Chattopadhyay D, Swingle MR, Salter EA, Wood E, D'Arcy B, Zivanov C, Abney K, Musiyenko A, Rusin SF, Kettenbach A, Yet L, Schroeder CE, Golden JE, Dunham WH, Gingras AC, Banerjee S, Forbes D, Wierzbicki A, Honkanen RE. Crystal structures and mutagenesis of PPP-family ser/thr protein phosphatases elucidate the selectivity of cantharidin and novel norcantharidin-based inhibitors of PP5C. Biochem Pharmacol. 2016 Jun 1;109:14-26. doi: 10.1016/j.bcp.2016.03.011. Epub 2016 Mar 23. PubMed PMID: 27002182; PubMed Central PMCID: PMC4853234. 5: Hsia TC, Lin JH, Hsu SC, Tang NY, Lu HF, Wu SH, Lin JG, Chung JG. Cantharidin induces DNA damage and inhibits DNA repair-associated protein levels in NCI-H460 human lung cancer cells. Environ Toxicol. 2015 Sep;30(10):1135-43. doi: 10.1002/tox.21986. Epub 2014 Mar 17. PubMed PMID: 24639390. 6: Le AP, Zhang LL, Liu W, Shi YF. Cantharidin inhibits cell proliferation and induces apoptosis through G2/M phase cell cycle arrest in hepatocellular carcinoma stem cells. Oncol Rep. 2016 May;35(5):2970-6. doi: 10.3892/or.2016.4684. Epub 2016 Mar 17. PubMed PMID: 26986084. 7: Simpson KM, Streeter RN, De Souza P, Genova SG, Morgan SE. Cantharidin toxicosis in 2 alpacas. Can Vet J. 2013 May;54(5):456-62. PubMed PMID: 24155427; PubMed Central PMCID: PMC3624911. 8: Huang Y, Wang Z, Zha S, Wang Y, Jiang W, Liao Y, Song Z, Qi Z, Yin Y. De Novo Transcriptome and Expression Profile Analysis to Reveal Genes and Pathways Potentially Involved in Cantharidin Biosynthesis in the Blister Beetle Mylabris cichorii. PLoS One. 2016 Jan 11;11(1):e0146953. doi: 10.1371/journal.pone.0146953. eCollection 2016. PubMed PMID: 26752526; PubMed Central PMCID: PMC4709229. 9: Wang WJ, Wu MY, Shen M, Zhi Q, Liu ZY, Gong FR, Tao M, Li W. Cantharidin and norcantharidin impair stemness of pancreatic cancer cells by repressing the β-catenin pathway and strengthen the cytotoxicity of gemcitabine and erlotinib. Int J Oncol. 2015 Nov;47(5):1912-22. doi: 10.3892/ijo.2015.3156. Epub 2015 Sep 11. PubMed PMID: 26398277. 10: Wu ZW, Yang XQ, Zhang YL. The Toxicology and Biochemical Characterization of Cantharidin on Cydia pomonella. J Econ Entomol. 2015 Feb;108(1):237-44. doi: 10.1093/jee/tou031. Epub 2015 Jan 8. PubMed PMID: 26470125. 11: Kuo JH, Shih TY, Lin JP, Lai KC, Lin ML, Yang MD, Chung JG. Cantharidin induces DNA damage and inhibits DNA repair-associated protein expressions in TSGH8301 human bladder cancer cell. Anticancer Res. 2015 Feb;35(2):795-804. PubMed PMID: 25667459. 12: Yang XQ, Zhang YL. Characterization of glutathione S-transferases from Sus scrofa, Cydia pomonella and Triticum aestivum: their responses to cantharidin. Enzyme Microb Technol. 2015 Feb;69:1-9. doi: 10.1016/j.enzmictec.2014.11.003. Epub 2014 Nov 24. PubMed PMID: 25640718. 13: Su CC, Liu SH, Lee KI, Huang KT, Lu TH, Fang KM, Wu CC, Yen CC, Lai CH, Su YC, Huang CF. Cantharidin Induces Apoptosis Through the Calcium/PKC-Regulated Endoplasmic Reticulum Stress Pathway in Human Bladder Cancer Cells. Am J Chin Med. 2015;43(3):581-600. doi: 10.1142/S0192415X15500366. PubMed PMID: 25967669. 14: Wu W, Su M, Li T, Wu K, Wu X, Tang Z. Cantharidin-induced liver injuries in mice and the protective effect of vitamin C supplementation. Int Immunopharmacol. 2015 Sep;28(1):182-7. doi: 10.1016/j.intimp.2015.06.003. Epub 2015 Jun 10. PubMed PMID: 26071218. 15: Tian X, Zeng G, Li X, Wu Z, Wang L. Cantharidin inhibits cell proliferation and promotes apoptosis in tongue squamous cell carcinoma through suppression of miR-214 and regulation of p53 and Bcl-2/Bax. Oncol Rep. 2015 Jun;33(6):3061-8. doi: 10.3892/or.2015.3942. Epub 2015 Apr 28. PubMed PMID: 25962755. 16: Huang Z, Zhang Y. Chronic Sublethal Effects of Cantharidin on the Diamondback Moth Plutella xylostella (Lepidoptera: Plutellidae). Toxins (Basel). 2015 May 29;7(6):1962-78. doi: 10.3390/toxins7061962. PubMed PMID: 26035491; PubMed Central PMCID: PMC4488684. 17: Li CC, Yu FS, Fan MJ, Chen YY, Lien JC, Chou YC, Lu HF, Tang NY, Peng SF, Huang WW, Chung JG. Anticancer effects of cantharidin in A431 human skin cancer (Epidermoid carcinoma) cells in vitro and in vivo. Environ Toxicol. 2017 Mar;32(3):723-738. doi: 10.1002/tox.22273. Epub 2016 Apr 25. PubMed PMID: 27113412. 18: Bajsa J, Pan Z, Duke SO. Cantharidin, a protein phosphatase inhibitor, strongly upregulates detoxification enzymes in the Arabidopsis proteome. J Plant Physiol. 2015 Jan 15;173:33-40. doi: 10.1016/j.jplph.2014.09.002. Epub 2014 Sep 16. PubMed PMID: 25462076. 19: Sun X, Cai X, Yang J, Chen J, Guo C, Cao P. Cantharidin Overcomes Imatinib Resistance by Depleting BCR-ABL in Chronic Myeloid Leukemia. Mol Cells. 2016 Dec;39(12):869-876. doi: 10.14348/molcells.2016.0023. Epub 2016 Dec 13. PubMed PMID: 27989101; PubMed Central PMCID: PMC5223104. 20: Huang Z, Wang Y, Zhang Y. Lethal and Sublethal Effects of Cantharidin on Development and Reproduction of Plutella xylostella (Lepidoptera: Plutellidae). J Econ Entomol. 2015 Jun;108(3):1054-64. doi: 10.1093/jee/tov057. Epub 2015 Mar 31. PubMed PMID: 26470229.