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Cantharidin information


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
CAS Number
  • 56-25-7 ☒N
3D model (JSmol)
  • Interactive image
Beilstein Reference
85302
ChEBI
  • CHEBI:64213
ChEMBL
  • ChEMBL48449 ☒N
ChemSpider
  • 2297293 checkY
ECHA InfoCard 100.000.240 Edit this at Wikidata
EC Number
  • 200-263-3
KEGG
  • C16778 ☒N
PubChem CID
  • 5944
UNII
  • IGL471WQ8P checkY
CompTox Dashboard (EPA)
  • DTXSID7041752 Edit this at Wikidata
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+ checkY
    Key: DHZBEENLJMYSHQ-YUMGAWCOSA-N checkY
SMILES
  • O=C2OC([C@@]1(C)[C@@H]3CC[C@@H](O3)[C@]12C)=O
Properties
Chemical formula
C10H12O4
Molar mass 196.202 g·mol−1
Density 1.41 g/cm3
Melting point 212 °C (414 °F; 485 K)
Pharmacology
ATC code
None
Legal status
  • NZ: Class A
  • US: ℞-only[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
GHS labelling:
Pictograms
GHS06: Toxic GHS07: Exclamation mark
Signal word
Danger
Hazard statements
H300, H315, H319, H335
Precautionary statements
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):
LD50 (median dose)
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).
☒N verify (what is checkY☒N ?)
Infobox references
Cantharidin
Clinical data
Trade namesYcanth, others
License data
  • US DailyMed: Cantharidin
Routes of
administration
Topical
Legal status
Legal status
  • US: ℞-only
Identifiers
CompTox Dashboard (EPA)
  • DTXSID7041752 Edit this at Wikidata
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. ^ https://www.fda.gov/drugs/news-events-human-drugs/fda-approves-first-treatment-molluscum-contagiosum
  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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Cantharidin

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Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use...

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Blister beetle

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Meloidae, so called for their defensive secretion of a blistering agent, cantharidin. About 7,500 species are known worldwide. Many are conspicuous and some...

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Spanish fly

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preparations as "Cantharides". The insect is the source of the terpenoid cantharidin, a toxic blistering agent once used as an exfoliating agent, anti-rheumatic...

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Tegrodera aloga

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spots found on its black body. The brightness of the spots warns of the cantharidin toxins the beetle carries; this coloration is known as aposematism, and...

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Korean bug

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aphrodisiac effect has not been clinically tested and is achieved by cantharidin inhibition of phosphodiesterase, protein phosphatase activity and stimulation...

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Molluscum contagiosum

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recommended above the others to shorten infection duration. Studies have found cantharidin to be an effective and safe treatment for removing molluscum contagiosum...

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Meloe

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(legs, neck, and antennae). This fluid is bright orange and contains cantharidin, a poisonous chemical compound. Wiping the chemical on skin can cause...

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Cauterization

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and pressed onto the lesion for a few moments. Trichloroacetic acid Cantharidin is an extract of the blister beetle that causes epidermal necrosis and...

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Moth

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Artificial fly Fly tying In medicine Apitherapy Apitoxin Melittin Spanish fly Cantharidin In mythology Bees in mythology Cicadas in mythology Scarab (artifact)...

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Blister agent

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chemical warfare agents, some naturally occurring substances such as cantharidin are also blister-producing agents (vesicants). Furanocoumarin, another...

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Meloe americanus

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joints containing the chemical cantharidin. Larvae, by contrast, excrete a milky fluid from their mouth. Cantharidin is stored in the beetle’s hemolymph...

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Ceroctis capensis

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charged with poisoning of participants in an orgy by the use of cantharidin. Cantharidin is toxic to vertebrates, the aposematic colouration of the beetles...

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Paederus dermatitis

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dermatitis", a term more properly used for the different dermatitis caused by cantharidin from blister beetles, is also sometimes used to describe paederus dermatitis...

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Pyrota insulata

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beetle, so called because if squeezed, it can produce an irritant called cantharidin that causes a blister on exposed human skin. Pyrota insulata is found...

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Median lethal dose

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(estimated) 0.001–0.002 Mercury(II) chloride (HgCl2) rat, oral 1 mg/kg 0.001 Cantharidin (from blister beetles) human, oral 500 μg/kg 0.0005 Aflatoxin B1 (from...

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Cantarella

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referring to the Spanish fly and other blister beetles that secrete cantharidin, a substance that is poisonous in large doses. Bradford, S. (2005). Lucrezia...

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Endothall

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experience stomach or intestine problems. Endothall is chemically related to cantharidin. Both compounds are protein phosphatase 2A inhibitors. Protein phosphatase...

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Berberomeloe majalis

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Bautista, L.M.; Blanco, G.; Alonso, J.C.; García-París, M. (2017). "Cantharidin is conserved across phylogeographic lineages and present in both morphs...

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Epicauta vittata

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fatalities, particularly of horses. Cantharidin toxicity in an animal may be called cantharidiasis. The cantharidin content of one striped blister beetle...

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C10H12O4

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refer to: Acetosyringone, a chemical compound Atraric acid Brevifolin Cantharidin, a poisonous chemical compound secreted by many species of blister beetles...

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EPA list of extremely hazardous substances

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Bromine Cadmium oxide Cadmium stearate Calcium arsenate Camphechlor Cantharidin Carbachol chloride Carbamic acid, Methyl-, O-(((2,4-Dimethyl-1...

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Wart

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approved by the U.S. Food and Drug Administration (FDA) for genital warts. Cantharidin, found naturally in the bodies of many members of the beetle family Meloidae...

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Joseph Lister

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started with mustard as an irritant, then Croton oil, acetic acid, oil of Cantharidin and chloroform and many others. They led to the production of three papers...

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Flea circus

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Artificial fly Fly tying In medicine Apitherapy Apitoxin Melittin Spanish fly Cantharidin In mythology Bees in mythology Cicadas in mythology Scarab (artifact)...

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Deathwatch beetle

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Artificial fly Fly tying In medicine Apitherapy Apitoxin Melittin Spanish fly Cantharidin In mythology Bees in mythology Cicadas in mythology Scarab (artifact)...

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Cardinal beetle

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communication between either members of the same or different species. Cantharidin (CTD) is a type of semiochemical that has different actions based on...

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