| Identification | More | [Name]
Cantharidin | [CAS]
56-25-7 | [Synonyms]
(1r,2s,3r,6s)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride
(3AA,4B,7B,7AA)-HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZOFURAN-1,3-DIONE
(3A-ALPHA,4B,7B,7A-ALPHA)-HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZOFURAN-1,3-DIONE
4,7-EPOXYISOBENZOFURAN-1,3-DIONE,HEXAHYDRO-3A,7A-DIMETHYL-, (3A,4,7,7A)-
CANTHARIDIN
dimethyl-3,6-epoxyperhydrophthalic anhydride
HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZO-FURAN-1,3-DIONE
,7-beta,7a-alpha)
1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride
1,2-dimethyl-3,6-epoxyperhydrophthalicanhydride
2,3-Dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride
2,3-dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylicanhydride
2,3-dimethyl-7-oxabicyclo(2.2.1)heptane-3-dicarboxylicanhydride
2,3-Dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylicacidanhydride
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aalpha,4beta,7beta,7aalpha)-
4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3a-alpha,4-beta
4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3aalpha,4beta,7
4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-,(3aalpha,4beta,7be
7aalpha)-bet | [EINECS(EC#)]
200-263-3 | [Molecular Formula]
C10H12O4 | [MDL Number]
MFCD00134968 | [Molecular Weight]
196.2 | [MOL File]
56-25-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Cantharidin is a brown to black powder.
| [Melting point ]
215-217 °C (lit.) | [Boiling point ]
253.08°C (rough estimate) | [density ]
1.0357 (rough estimate) | [refractive index ]
1.4699 (estimate) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO (25 mg/ml warm), acetone (8 mg/ml), ethanol (8 mg/ml warm), chloroform (1:65), ether (1:560), and ethyl acetate (1:150). | [form ]
solution | [color ]
white | [Water Solubility ]
30mg/L(20 ºC) | [Detection Methods]
NMR | [Merck ]
13,1757 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 weeks. | [InChIKey]
DHZBEENLJMYSHQ-XCVPVQRUSA-N | [LogP]
-0.409 (est) | [CAS DataBase Reference]
56-25-7(CAS DataBase Reference) | [IARC]
3 (Vol. 10, Sup 7) 1987 | [NIST Chemistry Reference]
Cantharidin(56-25-7) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
56-25-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+,T | [Risk Statements ]
R28:Very Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R38:Irritating to the skin.
R37:Irritating to the respiratory system.
R36:Irritating to the eyes.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 1
| [WGK Germany ]
3
| [RTECS ]
RN8575000
| [TSCA ]
Yes | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
29329990 | [Hazardous Substances Data]
56-25-7(Hazardous Substances Data) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Magnesium stearate-->Magnesium trisilicate-->Oils, animal, mixed with vegetable oil Me esters, sulfurized-->Pioneer Blue Natural Rubber Latex Gloves, Size 9-->1H,3H-4,7-Epoxy-3a,7a-(methanothiomethano)isobenzofuran-1,3-dione, tetrahydro-, (3aR,4R,7S,7aS)-rel--->3,4-Thiophenedicarboxylic acid, 2,5-dihydro-, dimethyl ester-->3,4-Thiophenedicarboxylic acid, 2,5-dihydro--->Thieno[3,4-c]furan-1,3(4H,6H)-dione-->3-Thiophenecarboxylic acid, 4-cyanotetrahydro-4-hydroxy-, methyl ester-->Methyl 4-oxotetrahydrothiophene-3-carboxylate-->DIMETHYL 3-THIAADIPATE-->Furan | [Preparation Products]
Cantharidin |
| Hazard Information | Back Directory | [General Description]
Brown to black powder or plates or scales. Formerly used as a counterirritant and vesicant. Used for the removal of warts. Used as an experimental anti tumor agent. Active ingredient in spanish fly, a reputed aphrodisiac. | [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. | [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 | [Fire Hazard]
When heated to decomposition CANTHARIDIN emits acrid smoke and irritating fumes. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. For ingestion, induce vomiting with syrup of
ipecac | [Shipping]
Cantharidin is not specifically listed in the DOT
Performance-Oriented Packaging Standards with respect
to labeling requirements or restrictions on shipping
quantities. | [Chemical Properties]
Cantharidin is a brown to black powder.
| [Chemical Properties]
white to light yellow crystal powde | [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. | [Definition]
ChEBI: A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A. | [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. | [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. | [storage]
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area. A regulated, marked area should be established where this chemical is handled, used, or stored incompliance with OSHA Standard 1910.1045. |
| Questions And Answer | Back Directory | [Description]
Cantharidin is a natural toxicant of blister beetles. Cantharidin has been used as a medicinal agent for over 2000 years and is listed as a drug under the name of Mylabris in the medical monograph Materia Medica published in 77 AD. Some of the most ancient Chinese prescriptions (306–168 BC) refer to the use of Mylabris for the treatment of furuncles and piles.
Cantharidin can be used for topically (0.7%) treatment of warts, in which the skin under the wart blisters, thereby, lifting the wart off the skin. It is used to treat molluscum contagiosum. Cantharidin is a strong inhibitor of protein phosphatases types 1 (PP1) and 2A (PP2A), which are potentially novel targets for anticancer therapies. Thus, cantharidin is exploited as anticancer drugs. Cantharidin is shown to be cytotoxic to cancer cells and stimulatory on the bone marrow. The renal toxicity of this drug has prevented its use in mainstream oncology.
| [Uses]
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. | [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
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