Structure via PubChem · Public domain (PubChem)
cantharidin
Sign in to saveAlso known as exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride, Cantharone, 1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride, Cantharidine, Kantharidin
Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use in pharmacology is treating molluscum contagiosum and warts topically. It is a burn agent, poisonous in large doses. It has been historically used as an aphrodisiac (in preparations sold under the name "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.
Key facts
- Drug.container_only
- yes
- Drug.tradename
- Ycanth, others
- Drug.DailyMedID
- Cantharidin
- Drug.routes_of_administration
- Topical
- Drug.legal_US
- Rx-only
- Drug.DrugBank
- DB12328
- Drug.C
- 10
- Drug.H
- 12
- Drug.O
- 4
via Wikipedia infobox
Chemical data
- Formula
- C10H12O4
- Molecular weight
- 196.2 g/mol
- IUPAC name
- (1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione
- SMILES
- C[C@@]12[C@H]3CC[C@@H]([C@@]1(C(=O)OC2=O)C)O3
- InChIKey
- DHZBEENLJMYSHQ-XCVPVQRUSA-N
- XLogP
- 0.6
- Polar surface area
- 52.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
1,321 papersvia PubMed
~14 min read
Encyclopedic overview
22 sectionsContents
- Chemistry
- Structure and nomenclature
- Distribution and availability
- Laboratory synthesis
- Biosynthesis
- History
- Aphrodisiac preparations
- Non-aphrodisiac uses
- Pharmaco-chemical isolation
- Other uses of the pharmacological isolate
- Veterinary issues
- Human medical issues
- General risks
- Risks of aphrodisiac use
- Research
- Mechanism of action
- Pharmaceutical use
- Toxicity
- Bioactivities
- Notes
- References
- External links
Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use in pharmacology is treating molluscum contagiosum and warts topically. It is a burn agent, poisonous in large doses. It has been historically used as an aphrodisiac (in preparations sold under the name "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 cantharidin 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.
Excerpted from Wikipedia’s “cantharidin” article, available under the CC BY-SA 4.0 licence.