Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H12O4 |
| Molecular Weight | 196.1999 |
| Optical Activity | NONE |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12[C@@H]3CC[C@@H](O3)[C@@]1(C)C(=O)OC2=O
InChI
InChIKey=DHZBEENLJMYSHQ-XCVPVQRUSA-N
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-
| Molecular Formula | C10H12O4 |
| Molecular Weight | 196.1999 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/24945640Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002193 and http://www.dormer.ca/DormerCos/WartRemovers.aspx
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24945640
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002193 and http://www.dormer.ca/DormerCos/WartRemovers.aspx
Cantharidin is 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). Cantharidin is a medication used to remove warts and a viral skin infection called molluscum contagiosum. It is made from the secretions that come from the green blister beetle in combination with salicylic acid. It works by creating a blister just below the wart, which pushes the wart up and away from the underlying tissue, cutting of the blood supply to the wart. As the blister and the wart dry out, they both slough off, leaving fresh, unmarred skin behind. It is also used as an experimental anti-tumor agent. Several studies also show potential novel applications of cantharidin in acquired perforating dermatosis, acute herpes zoster, and leishmaniasis. In 1962, cantharidin lost Food and Drug Administration (FDA) approval owing to the failure of its manufacturers to submit data attesting to cantharidin's efficacy. However, in 1999, the FDA included cantharidin on its “Bulk Substances List” of drugs which although not available as commercial products, were approved for compounding on a customized basis for individual patients.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Medulloblastoma cell growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/21735115 |
5.0 µM [IC50] | ||
Target ID: 1.05384904E8 Gene Symbol: LOC105384905 Sources: http://www.ncbi.nlm.nih.gov/pubmed/24132154 |
77.64 µM [IC50] | ||
Target ID: CHEMBL5869 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23983126 |
4.2 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | CANTHARONE PLUS Approved UseCANTHARONE PLUS is indicated for removal of warts, especially plantar and resistant and heavily keratinized warts. |
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.7 % 1 times / day multiple, topical Recommended Dose: 0.7 %, 1 times / day Route: topical Route: multiple Dose: 0.7 %, 1 times / day Sources: |
unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Pain, Blistering... Other AEs: Pain (23%) Sources: Blistering (92%) Abnormal pigmentation (46%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Pain | 23% | 0.7 % 1 times / day multiple, topical Recommended Dose: 0.7 %, 1 times / day Route: topical Route: multiple Dose: 0.7 %, 1 times / day Sources: |
unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: |
| Abnormal pigmentation | 46% | 0.7 % 1 times / day multiple, topical Recommended Dose: 0.7 %, 1 times / day Route: topical Route: multiple Dose: 0.7 %, 1 times / day Sources: |
unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: |
| Blistering | 92% | 0.7 % 1 times / day multiple, topical Recommended Dose: 0.7 %, 1 times / day Route: topical Route: multiple Dose: 0.7 %, 1 times / day Sources: |
unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression. | 2015-05 |
|
| The antiplasmodial activity of norcantharidin analogs. | 2010-11-15 |
|
| Effects of low-dose aspirin on acute inflammatory responses in humans. | 2009-08-01 |
|
| Effect of cantharidin, cephalotaxine and homoharringtonine on "in vitro" models of hepatitis B virus (HBV) and bovine viral diarrhoea virus (BVDV) replication. | 2007-06 |
|
| [Apoptosis induced by cantharidin in human pulmonary carcinoma cells A549 and its molecular mechanisms]. | 2005-06 |
|
| Toxin-induced tail phosphorylation of hepatocellular S6 kinase: evidence for a dual involvement of the AMP-activated protein kinase in S6 kinase regulation. | 2004-12 |
|
| Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. | 2003-12 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21735115
Cantharidin at concentrations higher than 30 uM rapidly inhibited cell
proliferation, with the cells killed in 24 h, treatment with Cantharidin at lower concentrations (1, 5, 10, 20, and 30 uM) was not as toxic at 24 h. For the DAOY cells and treatment for 72 h, for Cantharidin the IC50 for cell viability was 5.0 ± 0.4 uM.
| Substance Class |
Chemical
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IGL471WQ8P
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Validated (UNII)
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FDA ORPHAN DRUG |
359311
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IARC | Cantharidin |
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2181
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56-25-7
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11470
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64213
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5944
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SUB13227MIG
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200-263-3
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GH-82
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100000076607
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IGL471WQ8P
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IGL471WQ8P
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CANTHARIDIN
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DB12328
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DTXSID7041752
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m3025
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D002193
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C177086
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1984
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61805
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ACTIVE MOIETY |
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