Cantharidin

Cantharidin
Names
Preferred IUPAC name
(3aR,4S,7R,7aS)-3a,7a-Dimethylhexahydro-4,7-epoxy[2]benzofuran-1,3-dione
Other names
  • Cantharidin
  • Spanish fly
  • Ycanth
Identifiers
3D model (JSmol)
85302
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.240 Edit this at Wikidata
EC Number
  • 200-263-3
KEGG
UNII
  • 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+ checkY
    Key: DHZBEENLJMYSHQ-YUMGAWCOSA-N checkY
  • O=C2OC([C@@]1(C)[C@@H]3CC[C@@H](O3)[C@]12C)=O
Properties
C10H12O4
Molar mass 196.202 g·mol−1
Density 1.41 g/cm3
Melting point 212 °C (414 °F; 485 K)
Pharmacology
None
Topical
Legal status
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic
GHS labelling:
GHS06: Toxic GHS07: Exclamation mark
Danger
H300, H315, H319, H335
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
1
1
Lethal dose or concentration (LD, LC):
0.03–0.5 mg/kg (human)
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
Clinical data
Trade namesYcanth, others
License data
Routes of
administration		Topical
Legal status
Legal status
Identifiers
DrugBank
CompTox Dashboard (EPA)
ECHA InfoCard100.000.240 Edit this at Wikidata
Chemical and physical data
FormulaC10H12O4
Molar mass196.202 g·mol−1

Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles.[a] Its main current use in pharmacology is treating molluscum contagiosum and warts topically.[2] It is a burn agent and poisonous in large doses, and has been historically used as aphrodisiacs (Spanish fly). In its natural form, cantharidin is secreted by the male blister beetle, and given to the female as a copulatory gift during mating. Afterwards, the female beetle covers her eggs with it as a defense against predators.

Poisoning from cantharidin is a significant veterinary concern, especially in horses, but it can also be poisonous to humans if taken internally (where the source is usually experimental self-exposure). Externally, cantharidin is a potent vesicant (blistering agent), exposure to which can cause severe chemical burns. Properly dosed and applied, the same properties have also been used therapeutically, for instance, for treatment of skin conditions, such as molluscum contagiosum infection of the skin.

Cantharidin is classified as an extremely hazardous substance in the United States, and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.[3]

  1. ^ "Ycanth- cantharidin solution". DailyMed. 25 July 2023. Archived from the original on 29 August 2023. Retrieved 28 August 2023.
  2. ^ "FDA approves first treatment for molluscum contagiosum". FDA. 24 July 2023.
  3. ^ As defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002). See "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" Archived 25 February 2012 at the Wayback Machine (PDF) (1 July 2008 ed.). U.S. Government Printing Office. Retrieved 29 October 2011.


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