Cantharidine
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MedKoo CAT#: 540057

CAS#: 56-25-7 (lactone)

Description: Cantharidine (free base) is a PP1/2A inhibitor found in Canarthis vesicatoria. It inhibits proliferation of colorectal cancer cells, increases MCP-1, IL-6, and IL-β levels, and inhibits differentiation and resorptive activity of osteoclasts. This compound can produce severe skin inflammation, and is extremely toxic if ingested orally

Chemical Structure

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Cantharidine
CAS# 56-25-7 (lactone)
Instruction

Theoretical Analysis

MedKoo Cat#: 540057
Name: Cantharidine
CAS#: 56-25-7 (lactone)
Chemical Formula: C10H12O4
Exact Mass: 196.07
Molecular Weight: 196.200
Elemental Analysis: C, 61.22; H, 6.17; O, 32.62

Price and Availability

Size Price Availability Quantity
25mg USD 250 2 Weeks
100mg USD 450 2 Weeks
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Related CAS #: 56-25-7 (lactone)   76970-77-9 (imide)   1465-77-6 (sodium)    

Synonym: AI3-04021; AI304021; AI3 04021; BRN-0085302; BRN0085302; BRN 0085302; Cantharidine (free base); Cantharone; Kantaridin; Cantharidine

IUPAC/Chemical Name: (3aR,4S,7R,7aS)-3a,7a-dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione

InChi Key: DHZBEENLJMYSHQ-XCVPVQRUSA-N

InChi Code: InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9+,10-

SMILES Code: O=C(O1)[C@]2(C)[C@@](C1=O)(C)[C@@]3([H])CC[C@]2([H])O3

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: >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 196.20 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:

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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.