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Substance Name: Cantharidin [USAN]
RN: 56-25-7
UNII: IGL471WQ8P
InChIKey: DHZBEENLJMYSHQ-XCVPVQRUSA-N
Note
- 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.
Molecular Formula
- C10-H12-O4
Molecular Weight
- 196.2008
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Agricultural Chemical
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Herbicide
- Human Data
- Irritants
- Natural Product
- Noxae
- Riot Control Agents, Chemical
- Treatment of Molluscum Contagiosum
- Tumor Data
Superlist Classification Codes
- Overall Carcinogenic Evaluation: Group 3
- Threshold Planning Quantity (TPQ) = 100/10000 lb
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Names and Synonyms
Name of Substance
- Cantharidin
- Cantharidin [USAN]
- Cantharidine
MeSH Heading
- Cantharidin
Synonyms
- 1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride
- 2,3-Dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride
- 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-
- 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3a-alpha,4-beta,7-beta,7a-alpha)
- 5-19-05-00051 (Beilstein Handbook Reference)
- 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, 2,3-dimethyl-
- AI3-04021
- BRN 0085302
- CAN [Alkaloid]
- Cantharides camphor
- Cantharidin
- Cantharidine
- Cantharone
- Caswell No. 157
- CCRIS 635
- EINECS 200-263-3
- EPA Pesticide Chemical Code 013101
- exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride
- Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione
- Hexahydro-3aalpha,7aalpha-dimethyl-4beta,7beta-epoxyisobenzofuran-1,3-dione
- HSDB 2181
- Kantaridin
- Kantharidin
- Kantharidin [German]
- NSC 61805
- UNII-IGL471WQ8P
- WHO 11470
Systematic Names
- (1R,2S,3R,6S)-1,2-Dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride
- 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aalpha,4beta,7beta,7aalpha)-
- 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel-
- 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, 2,3-dimethyl-
- Cantharidin
Superlist Name
- Cantharidin
Registry Numbers
CAS Registry Number
- 56-25-7
FDA UNII
- IGL471WQ8P
Other Registry Number
- 1351357-43-1
System Generated Number
- 0000056257
Structure Descriptors
InChI
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-InChIKey
DHZBEENLJMYSHQ-XCVPVQRUSA-NSmiles
C[C@@]12[C@H]3CC[C@H](O3)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | oral | 310mg/kg (310mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
chicken | LDLo | subcutaneous | 75mg/kg (75mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
dog | LDLo | oral | 50mg/kg (50mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
frog | LDLo | oral | 7273mg/kg (7273mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
human | LDLo | oral | 428ug/kg (0.428mg/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 646, 1969. | |
mammal (species unspecified) | LD50 | intraperitoneal | 1710ug/kg (1.71mg/kg) | "Zhongliu Yanjiu" Cancer Review, Yu, R., et al., eds., Shanghai Science/Technology Publisher,Peop. Rep. China, 1994Vol. -, Pg. 183, 1994. | |
mammal (species unspecified) | LDLo | oral | 75mg/kg (75mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
mammal (species unspecified) | LDLo | unreported | 50mg/kg (50mg/kg) | Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 20, Pg. 135, 1989. | |
mouse | LD50 | intraperitoneal | 1mg/kg (1mg/kg) | Journal of Agricultural and Food Chemistry. Vol. 35, Pg. 823, 1987. | |
pigeon | LDLo | oral | 32mg/kg (32mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. | |
rabbit | LDLo | oral | 20mg/kg (20mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Toxicon. Vol. 23, Pg. 36, 1985. |
rabbit | LDLo | subcutaneous | 1mg/kg (1mg/kg) | "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 218 | deg C | EXP | |
log P (octanol-water) | 1.220 | (none) | EST | |
Water Solubility | 30 | mg/L | 20 | EXP |
Atmospheric OH Rate Constant | 1.68E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.