Cantharidin
| Cantharidin | |
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2,6-Dimethyl-4,10-dioxatricyclo- |
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Other names
Cantharidin |
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| Identifiers | |
| CAS number | 56-25-7  |
| ChemSpider | 2297293  |
| UNII | IGL471WQ8P |
| KEGG | C16778 |
| ChEMBL | CHEMBL48449 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C10H12O4 |
| Molar mass | 196.20 g/mol |
| Density | 1.41 g/cm³ |
| Melting point |
212 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Cantharidin, a type of terpenoid, is a poisonous chemical compound secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. The false blister beetles and cardinal beetles also have cantharidin.
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[edit] History
Cantharidin was first isolated in 1810 by Pierre Robiquet, a French chemist then living in Paris, from Lytta vesicatoria. Robiquet demonstrated that cantharidin was the actual principle responsible for the aggressively blistering properties of the coating of the eggs of that insect, and established that cantharidin had very definite toxic and poisonous properties comparable in degree to that of the most violent poisons known in the 19th century, such as strychnine.[1] It is an odorless and colorless solid at room temperature. It is secreted by the male blister beetle and given to the female during mating. Afterwards the female beetle will cover its eggs with it as a defense against predators. The complete mechanism of the biosynthesis is currently unknown.
[edit] Medical uses
Diluted solutions of cantharidin can be used as a topical medication to remove warts[2] and tattoos and to treat the small papules of Molluscum contagiosum.[3]
[edit] Medical risks for humans
Its potential for adverse effects has led it to being included in a list of "problem drugs" used by dermatologists[4] and emergency personnel.[5]
When ingested by humans, the LD50 is around 0.5 mg/kg, with a dose of as little as 10 milligrams being potentially fatal. Ingesting cantharidin can initially cause severe damage to the lining of the gastrointestinal and urinary tract, and may also cause permanent renal damage. Symptoms of cantharidin poisoning include haematuria, abdominal pains, and rarely priapism.[4]
The level of cantharidin in blister beetles can be quite variable: Among blister beetles of the genus Epicauta in Colorado, E. pennsylvanica contain approximately 0.2 mg, E. maculata contain 0.7 mg, and E. immaculata contain 4.8 mg per beetle; males also contain higher levels than females.[6]
The extreme toxicity of cantharidin makes any use as an aphrodisiac highly dangerous because it can easily cause death. As a result, it is illegal to sell (or use) cantharidin for this purpose in many countries.[citation needed]
[edit] Medical risks for animals
Horses are highly sensitive to cantharidin: the LD50 for horses is approximately 1 mg/kg of the horse's body weight. Horses may be accidentally poisoned when fed bales of fodder with blister beetles in them.[7]
[edit] Research
Topical treatment with cantharidin appears to have some effect in an animal model of cutaneous leishmaniasis.[8] In addition to topical medical applications, cantharidin and its analogues may have activity against cancer cells.[9][10][11] Laboratory studies with cultured tumor cell lines suggest that this activity may relate to inhibition of protein phosphatase 2A.[12][13]
[edit] References
- ^ Robiquet. M., Ann. Chim., 1810, vol. 76, pp. 302-307.
- ^ Epstein WL, Kligman AM (1958). "Treatment of warts with cantharidin". A. M. A. Archives of dermatology 77 (5): 508–11. PMID 13519856.
- ^ "Molluscum contagiosum". Merck Manuals. November 2005. http://www.merck.com/mmpe/sec10/ch122/ch122b.html. Retrieved 2007-10-21.
- ^ a b Binder R (1979). "Malpractice--in dermatology". Cutis; cutaneous medicine for the practitioner 23 (5): 663–6. PMID 456036.
- ^ Karras DJ, Farrell SE, Harrigan RA, Henretig FM, Gealt L (September 1996). "Poisoning from "Spanish fly" (cantharidin)". Am J Emerg Med 14 (5): 478–83. doi:10.1016/S0735-6757(96)90158-8. PMID 8765116.
- ^ Capinera JL, Gardner DR, Stermitz FR (1985-10). "Cantharidin Levels in Blister Beetles (Coleoptera: Meloidae) Associated with Alfalfa in Colorado". Journal of Economic Entomology 78 (5): 1052–1055. http://www.ingentaconnect.com/content/esa/jee/1985/00000078/00000005/art00011.
- ^ "Blister Beetle Poisoning / Cantharidin toxicosis". http://www.addl.purdue.edu/newsletters/2006/Fall/EquineCT.htm. Retrieved 2010-12-31.
- ^ Ghaffarifar, F. (2010). "Leishmania major: In vitro and in vivo anti-leishmanial effect of cantharidin". Experimental Parasitology 126 (2): 126–129. doi:10.1016/j.exppara.2010.04.004. PMID 20435039.
- ^ Ratcliffe, N. A.; Mello, C. B.; Garcia, E. S.; Butt, T. M.; Azambuja, P. (2011). "Insect natural products and processes: New treatments for human disease". Insect Biochemistry and Molecular Biology 41 (10): 747–769. doi:10.1016/j.ibmb.2011.05.007. PMID 21658450.
- ^ Chen, Y. N.; Cheng, C. C.; Chen, J. C.; Tsauer, W.; Hsu, S. L. (2003). "Norcantharidin-induced apoptosis is via the extracellular signal-regulated kinase and c-Jun-NH2-terminal kinase signaling pathways in human hepatoma HepG2 cells". British Journal of Pharmacology 140 (3): 461–470. doi:10.1038/sj.bjp.0705461. PMC 1574052. PMID 12970086. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1574052.
- ^ Zhang, C.; Peng, Y.; Wang, F.; Tan, X.; Liu, N.; Fan, S.; Wang, D.; Zhang, L. et al (2010). "A synthetic cantharidin analog for the enhancement of doxorubicin suppression of stem cell-derived aggressive sarcoma". Biomaterials 31 (36): 9535–9543. doi:10.1016/j.biomaterials.2010.08.059. PMID 20875681.
- ^ Dorn, D. C.; Kou, C. A.; Png, K. J.; Moore, M. A. S. (2009). "The effect of cantharidins on leukemic stem cells". International Journal of Cancer 124 (9): 2186–2199. doi:10.1002/ijc.24157. PMID 19123473.
- ^ Li, W.; Xie, L.; Chen, Z.; Zhu, Y.; Sun, Y.; Miao, Y.; Xu, Z.; Han, X. (2010). "Cantharidin, a potent and selective PP2A inhibitor, induces an oxidative stress-independent growth inhibition of pancreatic cancer cells through G2/M cell-cycle arrest and apoptosis". Cancer Science 101 (5): 1226–1233. doi:10.1111/j.1349-7006.2010.01523.x. PMID 20331621.
