56-25-7 Usage
Uses
Used in Pharmaceutical Industry:
Cantharidin is used as a potent inhibitor of PP2A phosphatase activity for the treatment of various types of cancer, including cervical, tongue, neuroblastoma, bone, leukemia, ovarian, colon, and other cancer cell lines. It is also used topically (0.7%) as an anti-wart treatment, which causes the skin under the wart to blister, lifting the wart off the skin.
Used in Veterinary Medicine:
Cantharidin is used as a vesicant, rubefacient, and counterirritant in veterinary medicine.
Used in Dermatology:
Cantharidin is used for the removal of warts and to treat molluscum contagiosum. It is also used as an experimental anti-tumor agent.
Used in Aphrodisiacs:
Cantharidin is an active ingredient in Spanish fly, a reputed aphrodisiac.
Chemical Properties:
Cantharidin is a brown to black powder or plates or scales. It is also described as a white to light yellow crystal powder. It is a monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure and is secreted by many species of blister beetle, most notably by the Spanish fly, Lytta vesicatoria.
Warning:
Cantharidin is a natural toxin and should be handled with care. Avoid skin contact, as it may cause skin irritation or blistering. Application by a physician is recommended due to its toxicity.
References
[1] Richard E. Honkanen (1993) Cantharidin, another natural toxin that inhibits the activity of serin/threonine protein phosphatases types 1 and 2A, 330, 283-286
[2] Jennette A. Sakoff, Stephen P. Ackland, Monique L. Baldwin, Mirella A. Keane, Adam
McCluskey (2002) Anticancer activity and protein phosphatase 1 and 2A inhibition of a new generation of cantharidin analogues, 20, 1-11
[3] Erin F. D. Mathes, Ilona J. Frieden (2010) Treatment of molluscum contagiosum with cantharidin: a practical approach, 39, 124-130
References
1) Honkanen (1993) Cantharidin, another natural toxin that inhibits the activity of serine/threonine protein phosphatases types 1 and 2A; FEBS Lett. 330 283
2) Wu et al. (2014) PP2A inhibitors suppress migration and growth of PANC-1 pancreatic cancer cells through inhibition on the Wnt/β-Catenin pathway by phosphorylation and degradation of β-catenin; Oncol. Rep., 32 513
3) Gong et al. (2015) PP2A inhibitors arrest G2/M transition through JNK/Sp1-dependent down-regulation of CDK1 and autophagy up-regulation of p21; Oncotarget, 6 18469
Indications
Cantharidin, from the beetle Cantharis vesicatoria, causes intraepidermal vesiculation
and is used in the treatment of warts and other benign cutaneous lesions.
Cantharidin is extremely toxic if taken internally; it should not be prescribed for
at-home use.Cantharidin (Cantharone), a mitochondrial poison derived from the blister beetle Cantharis vesicatoria, leads to changes in cell membranes, epidermal cell dyshesion, acantholysis, and blister formation and is also useful. Cantharidin can be compounded with salicylic acid and podophyllin resin; occlusion for only 2 hours is needed with this combination. Thick hyperkeratotic lesions should be pared down before painting. The lesion should then be painted with cantharidin, allowed to dry, and covered with Blenderm or other nonporous occlusive tape; 40% salicylic acid plaster may be used to achieve greater activity. The tape is left on for 24 hours or until the area begins to hurt. A blister, often hemorrhagic, will form, break, crust, and fall off in 7 to 14 days; at this time, the lesion is pared down, and any wart remnants are retreated. Because the effect of cantharidin is entirely intraepidermal, no scarring ensues. Ring-like or "donut configuration" recurrences may be seen occasionally after treatment with cantharidin or, at times, following liquid nitrogen therapy. Owing to this agent’s toxicity, application by a physician is recommended. Verrusol, which contains 30% salicylic acid, 5% podophyllin, and 1% cantharidin, may be used in the same manner.
Reactivity Profile
Organic anhydrides, such as Cantharidin, are incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
Hazard
Extremely toxic; questionable carcinogen;
powerful irritant to all cells and tissues; deadly poi-
son; respiratory failure; death.
Health Hazard
Cantharidin is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste of less than 7 drops for a 70 kg (150 lb.) person. It is very toxic by absorption through skin.
Fire Hazard
When heated to decomposition Cantharidin emits acrid smoke and irritating fumes.
Biological Activity
Natural toxin inhibitor of protein phosphatases 1 and 2A (K i values are 1.1 and 0.19 μ M respectively); similar to okadaic acid (9,10-Deepithio-9,10-didehydroacanthifolicin ). Displays > 500-fold selectivity over PP2B.
Biochem/physiol Actions
Inhibitor of protein phosphatase 2A.
Potential Exposure
Formerly used as a counterirritant and
vesicant. Also used for the removal of benign epithelial
growths, e.g., warts. Used as an experimental antitumor
agent. The active ingredient in “Spanish fly,” a reputed
aphrodisia
Shipping
Cantharidin is not specifically listed in the DOT
Performance-Oriented Packaging Standards with respect
to labeling requirements or restrictions on shipping
quantities.
Waste Disposal
It is inappropriate and possibly dangerous to the environment to dispose of expired or
waste drugs and pharmaceuticals by flushing them down
the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed
with wet cat litter or coffee grounds, double-bagged in
plastic, discard in trash. Larger quantities shall carefully
take into consideration applicable DEA, EPA, and FDA
regulations. If possible return the pharmaceutical to the
manufacturer for proper disposal being careful to properly
label and securely package the material. Alternatively, the
waste pharmaceutical shall be labeled, securely packaged,
and transported by a state licensed medical waste contractor
to dispose by burial in a licensed hazardous or toxic waste
landfill or incinerator.
Check Digit Verification of cas no
The CAS Registry Mumber 56-25-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 56-25:
(4*5)+(3*6)+(2*2)+(1*5)=47
47 % 10 = 7
So 56-25-7 is a valid CAS Registry Number.
InChI:InChI=1/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+
56-25-7Relevant articles and documents
SYNTHESIS OF CANTHARIDIN
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Paragraph 00259, (2019/04/27)
The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds {i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions {e.g., infectious diseases and skin conditions).
Novel green and environment-friendly synthetic process for cantharidin
-
, (2017/08/10)
The invention relates to a novel green and environment-friendly synthetic process for preparing cantharidin under the condition of normal pressure and belongs to the field of synthesis and preparation of medicines. The process comprises the following steps: preparing 3-cyano-3-hydroxy-4-methyl formate-2,5-tetrahydrothiophene from a NaCN aqueous solution; adding benzene, pyridine and POCl3 into thiophene to prepare 3-cyano-4-methyl formate-2,5-dihydrothiophene; then adding acetic acid and concentrated hydrochloric acid, and carrying out reflux reaction to obtain 2,5-dihydrothiophene-3,4-dicarboxylic acid powder; carrying out stirring and refluxing on the prepared dicarboxylic acid and thionyl chloride to prepare 2,5-dihydrothiophene-3,4-dicarboxylic anhydride; carrying out heating reaction according to the solid-liquid ratio of dicarboxylic anhydride to furfuran to ionic liquid being 1mg:(3.5 to 6[mu]l):(2 to 4[mu]l), extracting and carrying out Raney-Ni reflux to obtain the cantharidin. According to the process, superhigh pressure condition and equipment are not needed, and overnight reaction at the temperature of 20 to 50DEG C is carried out; the process has the advantages of mild conditions, high conversion rate, and high yield of the cantharidin, and provides favorable conditions for industrial production of the cantharidin.
COMMERCIALLY VIABLE SYNTHESIS OF CANTHARIDIN AND BIOACTIVE CANTHARIDIN DERIVATIVES
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Paragraph 0126-0127, (2016/07/05)
The present disclosure provides methods for synthesizing cantharidin and cantharidin derivatives.
