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Merck

C7632

Cantharidin

protein phosphatase 2 A (PPA2) inhibitor

Synonym(s):

3a,7a-Dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione, 7a-Dimethylhexahydro-3a,4,7-epoxyisobenzofuran, Cantharidine, Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione

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About This Item

Empirical Formula (Hill Notation):
C10H12O4
CAS Number:
56-25-7
Molecular Weight:
196.20
NACRES:
NA.77
PubChem Substance ID:
24278334
UNSPSC Code:
12352200
EC Number:
200-263-3
MDL number:
MFCD00134968

Product Name

Cantharidin,

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-

InChI key

DHZBEENLJMYSHQ-XCVPVQRUSA-N

SMILES string

C[C@]12C3CCC(O3)[C@@]1(C)C(=O)OC2=O

color

white

mp

215-217 °C (lit.)
215-218 °C

solubility

DMSO: soluble
ethanol: soluble

Quality Level

200

Gene Information

human ... PPP2CA(5515), PPP2CB(5516), PPP2CBP(5517), PPP2R1A(5518), PPP2R1B(5519), PPP2R2A(5520), PPP2R2B(5521), PPP2R2C(5522), PPP2R3A(5523), PPP2R5A(5525)

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Application

Cantharidin has been used to inhibit protein phosphatase 2 (PP2A).

Biochem/physiol Actions

Inhibitor of protein phosphatase 2A.

General description

Cantharidin is a poisonous vesicant, which is produced by blister bees. It is used to treat piles, ulcers, venomous worms and tuberculous scrofuloderma. It is used as an aphrodisiac, abortifacient and a veterinary medicine diuretic.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM7986
BCCL3516
BCCK0647
BCCJ4895
BCCF1280

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T I Baskin et al.
Plant physiology, 113(2), 493-502 (1997-02-01)
To investigate molecular mechanisms controlling plant morphogenesis, we examined the morphology of primary roots of Arabidopsis thaliana and the organization of cortical microtubules in response to inhibitors of serine/threonine protein phosphatases and kinases. We found that cantharidin, an inhibitor of
Heat Oscillations Driven by the Embryonic Cell Cycle Reveal the Energetic Costs of Signaling
Rodenfels J, et al.
Developmental Cell (2019)
Ali Thaqi et al.
European journal of medicinal chemistry, 45(5), 1717-1723 (2010-02-16)
Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer
Hong-Chang Li et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 43(5), 1829-1840 (2017-10-20)
Cantharidin, a type of terpenoid secreted by the blister beetle Mylabris phalerata (Pallas), has attracted great attention in cancer therapy because of its potential anti-cancer activities. Here, we report the effects on apoptosis and autophagy in human triple-negative breast cancer
Cécile Segonzac et al.
The EMBO journal, 33(18), 2069-2079 (2014-08-03)
Recognition of pathogen-associated molecular patterns (PAMPs) by surface-localized pattern-recognition receptors (PRRs) activates plant innate immunity, mainly through activation of numerous protein kinases. Appropriate induction of immune responses must be tightly regulated, as many of the kinases involved have an intrinsic
View All Related Papers

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