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Chemistry

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Also known as: 56-25-7, Cantharidine, Cantharone, Kantaridin, Cantharides camphor, Kantharidin
Molecular Formula
C10H12O4
Molecular Weight
196.20  g/mol
InChI Key
DHZBEENLJMYSHQ-XCVPVQRUSA-N
FDA UNII
IGL471WQ8P

Cantharidin
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). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.
1 2D Structure

Cantharidin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione
2.1.2 InChI
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-
2.1.3 InChI Key
DHZBEENLJMYSHQ-XCVPVQRUSA-N
2.1.4 Canonical SMILES
CC12C3CCC(C1(C(=O)OC2=O)C)O3
2.1.5 Isomeric SMILES
C[C@@]12[C@H]3CC[C@@H]([C@@]1(C(=O)OC2=O)C)O3
2.2 Other Identifiers
2.2.1 UNII
IGL471WQ8P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cantharides

2. Cantharidine

2.3.2 Depositor-Supplied Synonyms

1. 56-25-7

2. Cantharidine

3. Cantharone

4. Kantaridin

5. Cantharides Camphor

6. Kantharidin

7. 1,2-dimethyl-3,6-epoxyperhydrophthalic Anhydride

8. Cantaridina

9. Cantharidinum

10. Exo-1,2-cis-dimethyl-3,6-epoxyhexahydrophthalic Anhydride

11. Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione

12. Nsc61805

13. Brn 0085302

14. Cantharidin [usan]

15. Ai3-04021

16. (3ar,4s,7r,7as)-3a,7a-dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione

17. Nsc-61805

18. Igl471wq8p

19. Chembl48449

20. 4,7-epoxyisobenzofuran-1,3-dione, Hexahydro-3a,7a-dimethyl-, (3ar,4s,7r,7as)-rel-

21. Chebi:64213

22. 2,3-dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic Anhydride

23. Can [alkaloid]

24. Mfcd00134968

25. Cantharidin (usan)

26. Nsc 61805

27. Kantharidin [german]

28. Caswell No. 157

29. (3a?,4?,7?,7a?)-hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione

30. 4,7-epoxyisobenzofuran-1,3-dione, Hexahydro-3a,7a-dimethyl-,(3ar,4s,7r,7as)-rel-

31. Ccris 635

32. 4,7-epoxyisobenzofuran-1,3-dione, Hexahydro-3a,7a-dimethyl-

33. 7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic Anhydride, 2,3-dimethyl-

34. Hsdb 2181

35. Einecs 200-263-3

36. Unii-igl471wq8p

37. Epa Pesticide Chemical Code 013101

38. 7a-dimethylhexahydro-3a,4,7-epoxyisobenzofuran

39. Cas-56-25-7

40. Ncgc00016247-01

41. 3a,7a-dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione

42. Cantharidin [mi]

43. Prestwick3_000885

44. Cantharidin [inn]

45. Cantharidin [iarc]

46. (1r,2s,3r,6s)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic Anhydride

47. 2,3-dicarboxylic Anhydride

48. Cantharidin [vandf]

49. Cantharidine [hsdb]

50. Hexahydro-3aalpha,7aalpha-dimethyl-4beta,7beta-epoxyisobenzofuran-1,3-dione

51. Ncimech_000301

52. Cantharidin [mart.]

53. Cantharidinum [hpus]

54. Bspbio_000670

55. Cantharidin [who-dd]

56. 4,7-epoxyisobenzofuran-1,3-dione, Hexahydro-3a,7a-dimethyl-, (3a-alpha,4-beta,7-beta,7a-alpha)

57. 5-19-05-00051 (beilstein Handbook Reference)

58. Schembl152262

59. Bpbio1_000738

60. Cantharides Camphor, Cantharone

61. Cid_6708701

62. Hms2097b12

63. Hms3412j13

64. Hms3676j13

65. 1,6-epoxyperhydrophthalic Anhydride

66. 4,7-epoxyisobenzofuran-1,3-dione, Hexahydro-3a,7a-dimethyl-, (3a.alpha.,4.beta.,7.beta.,7a.alpha.)-

67. Act03236

68. Amy33451

69. Bcp09819

70. Hy-n0209

71. Bdbm50090505

72. Ccg-35382

73. Ccg-36082

74. Who 11470

75. Zinc17611186

76. Akos015895930

77. Ac-7967

78. Cs-4979

79. Db12328

80. 4,3-dione, Hexahydro-3a,7a-dimethyl-

81. Exo-1,6-epoxyhexahydrophthalic Anhydride

82. Ncgc00025212-02

83. Ncgc00025212-03

84. Ncgc00025212-04

85. Ncgc00025212-05

86. Ncgc00025212-31

87. As-18735

88. Nci60_005413

89. Wln: T C555 A Ao Dvovtj C1 G1

90. Ab00513946

91. Hexahydro-3a,7-epoxyisobenzofuran-1,3-dione

92. D11745

93. 7-oxabicyclo[2.2.1]heptane-2, 2,3-dimethyl-

94. 134c968

95. Q410884

96. Sr-01000597585

97. Sr-01000597585-1

98. Brd-k80684056-001-01-0

99. Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzo-furan-1,3-dione

100. (3ar,4s,7r,7as)-3a,7a-dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione

101. (1r,2s,6r,7s)-2,6-dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

102. (1r,5s,6r,9s)-rel-1,5-dimethyl-3,10-dioxatricyclo(3.2.1.01,5)decane-2,4-dione

103. (1r,7s)-2,6-dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

104. (1s,2r,6s,7r)-2,6-dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

105. (1s,2r,6s,7r)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione

106. (1s,3s,4r,7r)-2,6-dimethyl-4,10-dioxa-tricyclo[5.2.1.0-2,6]decane-3,5-dione

107. 4,3-dione, Hexahydro-3a,7a-dimethyl-, (3a.alpha.,4.beta.,7.beta.,7a.alpha.)-

108. Cantharidin:4,7-epoxyisobenzofuran-1,3-dione,hexahydro-3a,7a- Dimethyl-, (3a,4,7,7a)-,

109. Hexahydro-3a.alpha.,7a.alpha.-dimethyl-4.beta.,7.beta.-epoxyisobenzofuran-1,3-dione

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 196.20 g/mol
Molecular Formula C10H12O4
XLogP30.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass196.07355886 g/mol
Monoisotopic Mass196.07355886 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count14
Formal Charge0
Complexity318
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Enzyme Inhibitors; Irritants

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


EXPTL USE: CANTHARIDIN AS ANTICANCER AGENTS.

PMID:7246474 HSU B; AM J CHIN MED 8 (4): 301 (1980)


EXPTL USE: APPLICATION OF MYLABRIS CANTHARIDIN IS AN ACTIVE COMPONENT OF MYLABRIS IN CANCER TREATMENT.

WANG K; YAO HSUEH T'UNG PAO 15 (3): 23 (1980)


EXPTL USE: IN MICE INOCULATED WITH 2 MILLION CELLS OF ASCITES HEPATOMA, ADMIN OF CANTHARIDIN (1.25 MG/KG/DAY FOR 7 DAYS, IP) PROLONGED SURVIVAL PERIOD BY 20.8-61.5%. CANTHARIDIN HAD NO THERAPEUTIC ACTION ON SARCOMA 180 IN MICE OR WALKER TUMOR IN RATS.

CHEN R ET AL; CHIN MED J (PEKING, ENGL ED) 93 (3): 183 (1980)


For more Therapeutic Uses (Complete) data for CANTHARIDINE (9 total), please visit the HSDB record page.


4.2 Drug Indication

The only therapeutic use for which cantharidin is currently primarily indicated for is as an active ingredient in topical agents for treating common warts (verruca vulgaris), periungual warts, plantar warts, and molluscum contagiosum. At the same time, such topical cantharidin applications have also been used for a number of off-label indications like callus removal, cutaneous leishmaniasis, herpes zoster, and acquired perforating dermatosis. Furthermore, since most topical cantharidin applications are most commonly available in a 0.7% formulation or a more potent 1% mixture, the 0.7% formulation is most commonly indicated for the treatment of common warts, periungual warts, and molluscum contagiosum while the more potent 1% mixture is typically limited only for use by healthcare professionals in a clinical setting for treating plantar warts and other more specialized off-label conditions. Moreover, there have also been studies into whether or not cantharidin could be effective at being used as an inflammatory model or in cancer treatment - either of which has yet to formally elucidate any results.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cantharidin is a natural toxin produced by the blistering beetle that possesses both vesicant (blistering) and keratolytic effects. The substance elicits these effects by inducing acantholysis (loss of intercellular connections) through the targeting of the desmosomal dense plaque, resulting in the detachment of the desmosomes from the tonofilaments. Cantharidin's effectiveness against warts is proposed to be a result of the exfoliation of the wart body as a consequence of the compound's acantholytic action. This acantholytic action generally does not go beyond the epidermal cells so that the basal layer remains intact and minimal effect occurs on the corium. There is consequently no scarring from the topical application of cantharidin.


5.2 MeSH Pharmacological Classification

Irritants

Drugs that act locally on cutaneous or mucosal surfaces to produce inflammation; those that cause redness due to hyperemia are rubefacients; those that raise blisters are vesicants and those that penetrate sebaceous glands and cause abscesses are pustulants; tear gases and mustard gases are also irritants. (See all compounds classified as Irritants.)


Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


5.3 Absorption, Distribution and Excretion

Absorption

Cantharidin is absorbed from the gastrointestinal tract, and, to a limited extent from the skin as well. Little pharmacodynamic and pharmacokinetic data regarding cantharidin in the human body currently exists; recruitment for First-Time-In-Human clinical trials regarding such information have been ongoing in 2018. There are however some studies regarding such data in animal models like beagle dogs.


Route of Elimination

It has been observed that absorbed cantharidin is excreted by the kidney. Little pharmacodynamic and pharmacokinetic data regarding cantharidin in the human body currently exists; recruitment for First-Time-In-Human clinical trials regarding such information have been ongoing in 2018. There are however some studies regarding such data in animal models like beagle dogs.


Volume of Distribution

After oral or IP injection of (3)H-labeled cantharidin, high levels of radioactivity distributed to and were exhibited in the bile, kidney, liver, stomach, and tumor cells of ascites hepatoma-bearing mice. Such distribution suggests the agent has an affinity for liver and tumor tissues. Little pharmacodynamic and pharmacokinetic data regarding cantharidin in the human body currently exists; recruitment for First-Time-In-Human clinical trials regarding such information have been ongoing in 2018. There are however some studies regarding such data in animal models like beagle dogs.


Clearance

Little pharmacodynamic and pharmacokinetic data regarding cantharidin in the human body currently exists; recruitment for First-Time-In-Human clinical trials regarding such information have been ongoing in 2018. There are however some studies regarding such data in animal models like beagle dogs.


THE DRUG IS ABSORBED FROM GI TRACT AND, TO LIMITED EXTENT, FROM SKIN. IT IS EXCRETED BY KIDNEY.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 952


BILE, KIDNEY, LIVER, STOMACH & TUMOR CELLS OF ASCITES HEPATOMA-BEARING MICE EXHIBITED A HIGH LEVEL OF RADIOACTIVITY AFTER ORAL OR IP INJECTION OF (3)H-LABELED CANTHARIDIN. DISTRIBUTION SUGGESTS IT HAS AFFINITY TO LIVER & TUMOR TISSUES.

CHEN R ET AL; CHIN MED J (PEKING, ENGL ED) 93 (3): 183 (1980)


5.4 Metabolism/Metabolites

Little pharmacodynamic and pharmacokinetic data regarding cantharidin in the human body currently exists; recruitment for First-Time-In-Human clinical trials regarding such information have been ongoing in 2018. There are however some studies regarding such data in animal models like beagle dogs.


5.5 Biological Half-Life

Little pharmacodynamic and pharmacokinetic data regarding cantharidin in the human body currently exists; recruitment for First-Time-In-Human clinical trials regarding such information have been ongoing in 2018. There are however some studies regarding such data in animal models like beagle dogs.


5.6 Mechanism of Action

Cantharidin is specifically absorbed by lipids in the membrane of epidermal keratinocytes, where it activates the release of neutral serine proteases. These enzymes subsequently break the peptide bonds in surrounding proteins, leading to the progressive degeneration of desmosomal dense plaques, which are important cellular structures that participate in cell-to-cell adhesion. Such degeneration results in the detachment of the tonofilaments that hold cells together. This process as a whole leads to the selective acantholysis (loss of cellular connections) and blistering of the skin when the cantharidin topical application is applied upon specific topical developments like warts. A blister(s) at the application site develop within 24 to 48 hours of application and typically resolve within 4 to 7 days. Factors that can modify this proposed time frame include the volume or concentration of cantharidin used, physical contact time of the applied compound (usually between 4 to 24 hours), the presence of any occlusive dressings, or even patient sensitivity to cantharidin. The blistered lesions ultimately heal without scarring. Finally, there are some studies that suggest cantharidin's chemical profile as a potent and selective inhibitor of protein phosphatase 2A confers upon it an oxidative stress-independent growth inhibition of pancreatic cancer cells through cancer cell-cycle arrest and apoptosis. Nevertheless, the fact that little data regarding the pharmacodynamics and pharmacokinetics of cantharidin in the human body exists and certain toxic effects of cantharidin that have been observed following oral ingestion in humans like ulceration of the gastrointestinal and genitourinary tracts, along with electrolyte and renal function disturbance are strong reasons as to why the compound currently lacks FDA approval is used fairly limitedly for formal therapeutic indications.


Cantharidine totally inhibits the phosphorylase a phosphatase activity in mouse liver, muscle, and skin cytosol at 5000 nM, with IC50s of 110-250 nM. About 50% of the phosphorylase a phosphatase activity of brain cytosol is sensitive to cantharidine with an IC50 of approximately 80 nM and the remaining half is not inhibited even at 5000 nM.

PMID:7839375 Eldridge R, Casida JE; Toxicol Appl Pharmacol 130 (1): 95-100 (1995)


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