Cantharidin: Difference between revisions
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Cantharidin Research: In addition to topical medical applications of Cantharidin, a wide body of research is now focused in its ability to kill a variety of cancers. The anti-cancer properties of this compound are rooted in thousands of years of traditional Chinese folk and traditional medical practices that used different species of dried blister beetles to treat cancer |
Cantharidin Research: In addition to topical medical applications of Cantharidin, a wide body of research is now focused in its ability to kill a variety of cancers. The anti-cancer properties of this compound are rooted in thousands of years of traditional Chinese folk and traditional medical practices that used different species of dried blister beetles to treat cancer. As reviewed by N.A. Ratcliffe et al. in 2011, in-vitro and in animal models, Cantharidin has been demonstrated to kill tumor cells including: |
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<ref>Wang, G.S., 1989. Medical uses of mylabris in ancient China and recent studies. J. Ethnopharmacol. 26, 147e162.</ref> |
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Hepatomas (Mack et al. 1996) |
Hepatomas (Mack et al. 1996) |
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Revision as of 03:12, 6 December 2011
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| Names | |
|---|---|
| IUPAC names
2,6-Dimethyl-4,10-dioxatricyclo-
[5.2.1.02,6]decane-3,5-dione | |
| Other names
Cantharidin
| |
| Identifiers | |
3D model (JSmol)
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|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.240 |
| KEGG | |
| UNII | |
CompTox Dashboard (EPA)
|
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| |
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| Properties | |
| C10H12O4 | |
| Molar mass | 196.20 g/mol |
| Density | 1.41 g/cm³ |
| Melting point | 212 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
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.
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]
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]
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]
Research
Topical treatment with cantharidin appears to have some effect in an animal model of cutaneous leishmaniasis.[8]
Cantharidin Research: In addition to topical medical applications of Cantharidin, a wide body of research is now focused in its ability to kill a variety of cancers. The anti-cancer properties of this compound are rooted in thousands of years of traditional Chinese folk and traditional medical practices that used different species of dried blister beetles to treat cancer. As reviewed by N.A. Ratcliffe et al. in 2011, in-vitro and in animal models, Cantharidin has been demonstrated to kill tumor cells including:
Hepatomas (Mack et al. 1996) Leukaemia (Dorn et al. 2009) Breast Cancer (Huang et al. 2009) Melanoma (An et al. 2004) Bladder and gall bladder carcinomas (Fan et al. 2006)N Colorectal carcinoma Peng et al 2002) Pancreatic Cancer (Li et al. 2010)
Laboratory studies with cultured tumor cell lines[10][11] suggest that cantharidin analogs might have anti-cancer activity through the inhibition of protein phosphatase 2A.
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. 2005. Retrieved 2007-10-21.
{{cite web}}: Unknown parameter|month=ignored (help) - ^ 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 (1996). "Poisoning from "Spanish fly" (cantharidin)". Am J Emerg Med. 14 (5): 478–83. doi:10.1016/S0735-6757(96)90158-8. PMID 8765116.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}: Check date values in:|date=(help)CS1 maint: multiple names: authors list (link) - ^ "Blister Beetle Poisoning / Cantharidin toxicosis". Retrieved 2010-12-31.
- ^ Ghaffarifar F (2010). "Leishmania major: in vitro and in vivo anti-leishmanial effect of cantharidin". Exp. Parasitol. 126 (2): 126–9. doi:10.1016/j.exppara.2010.04.004. PMID 20435039.
{{cite journal}}: Unknown parameter|month=ignored (help) - ^ Wang, G.S., 1989. Medical uses of mylabris in ancient China and recent studies. J. Ethnopharmacol. 26, 147e162.
- ^ Chang C, Zhu YQ, Mei JJ, Liu SQ, Luo J (2010). "Involvement of mitochondrial pathway in NCTD-induced cytotoxicity in human hepG2 cells". J. Exp. Clin. Cancer Res. 29 (1): 145. doi:10.1186/1756-9966-29-145. PMC 2987898. PMID 21059274.
{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link) - ^ Zhang C, Peng Y, Wang F; et al. (2010). "A synthetic cantharidin analog for the enhancement of doxorubicin suppression of stem cell-derived aggressive sarcoma". Biomaterials. 31 (36): 9535–43. doi:10.1016/j.biomaterials.2010.08.059. PMID 20875681.
{{cite journal}}: Explicit use of et al. in:|author=(help); Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link)