Cantharidin

Base Information

• Chemical Name: Cantharidin
• CAS No.: 56-25-7
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID7041752
• Pharos Ligand ID: Y158V373LA4C
• ChEMBL ID: CHEMBL299846
• Mol file: 56-25-7.mol

Synonyms:4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a-dimethyl-, (3aa,4b,7b,7aa)-;7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylicanhydride, 2,3-dimethyl- (8CI);Cantharidin (6CI,7CI);1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride;Cantharidine;Cantharone;Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione;Kantaridin;NSC 61805;

Chemical Property of Cantharidin

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00021mmHg at 25°C
• Melting Point: 215-217 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 326.869 °C at 760 mmHg
• Flash Point: 146.137 °C
• PSA: 52.60000
• Density: 1.362 g/cm³
• LogP: 0.64360
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (25 mg/ml warm), acetone (8 mg/ml), ethanol (8 m
• Water Solubility.: 30mg/L(20 oC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 318

Purity/Quality:

99%, ^*data from raw suppliers

Cantharidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T+,T
• Statements: 28-36/37/38-38-37-36-23/24/25
• Safety Statements: 53-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12C3CCC(C1(C(=O)OC2=O)C)O3
• Isomeric SMILES: C[C@]12C3CCC([C@]1(C(=O)OC2=O)C)O3
• 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. Cantharidin (56-25-7) inhibits protein phosphatase 2A (Ki=0.19 μM) and PP1 (Ki=1.1 μM).1 Displays >500-fold selectivity over PP2B. Suppresses growth and migration of PANC-1 pancreatic cancer cells via phosphorylation and degradation of β-catenin.2?Cantharidin arrests G2/M transition via JNK/Sp1-dependent down-regulation of CDK1.3?Cell permeable. Warning: Avoid skin contact, may cause skin irritation or blistering.
• 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. Cantharidin is used as a potent inhibitor of PP2A phosphatase activity. It has been shown to stimulate cell cycle progression and induce premature mitosis, used topically (0.7%) as an anti-wart treatment, and has been shown to be active in cervical, tongue, neuroblastoma, bone, leukemia, ovarian, colon, and various other cancer cell lines. In veterinary medicine as a vesicant, rubefa- cient, and counterirritant. Cantharidin is a natural toxin produced by blister beetles that moderately inhibits protein phosphatases 1 (PP1) (IC50 = 1.7 μM) and PP2A (IC50 = 0.2 μM) and only weakly inhibits the activity of PP2B (IC50 = 1 mM). It has been shown to stimulate cell cycle progression and induce premature mitosis, used topically (0.7%) as an anti-wart treatment, and has been shown to be active in cervical, tongue, neuroblastoma, bone, leukemia, ovarian, colon, and various other cancer cell lines.
• 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.

Technology Process of Cantharidin

There total 22 articles about Cantharidin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

furan (110-00-9) + 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride (75532-25-1) → cantharidin (56-25-7)

Guidance literature:

furan; 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride; With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 50 ℃; for 19h;

In ethyl acetate; for 4h; Reagent/catalyst; Temperature; Reflux;

Reference yield: 59.0%

C10H10O4S (75538-64-6) → cantharidin (56-25-7)

Guidance literature:

With hydrogen; In ethyl acetate; under 760.051 Torr; Reflux;

Reference yield:

C10H8O4S (75532-26-2) → cantharidin (56-25-7)

Guidance literature:

With hydrogen; In water; ethyl acetate; for 4h; Reflux;

upstream raw materials:

furan

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

C₁₀H₁₀O₄S

hydrogenchloride

Downstream raw materials:

2-benzylidenamino-3a,7a-dimethyl-(3at,7at)-hexahydro-4r,7c-epoxido-isoindole-1,3-dione

Refernces

• 1、 -. "SYNTHESIS OF CANTHARIDIN". Paragraph 00259. . Retrieved 2019/04/27.
• 2、 -. "COMMERCIALLY VIABLE SYNTHESIS OF CANTHARIDIN AND BIOACTIVE CANTHARIDIN DERIVATIVES". Paragraph 0126-0127. . Retrieved 2016/07/05.