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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
 

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-N

Smiles

C[C@@]12[C@H]3CC[C@H](O3)[C@]1(C)C(=O)OC2=O

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.