Cantharidin

Names

[ CAS No. ]:
56-25-7

[ Name ]:
Cantharidin

[Synonym ]:
2endo,3endo-dimethyl-7-oxa-norbornane-2exo,3exo-dicarboxylic acid-anhydride
3a,7a-dimethyl-(3at,7at)-hexahydro-4r,7c-epioxido-isobenzofuran-1,3-dione
cantharides
MFCD00134968
2,3-dimethyl anhydride
Canthari
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-
Antharidin
Kantaridin
Cantharone
Cantharidin
7aalpha)-t
4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aα,4β,7β,7aα)-
Kantharidin
7aalpha)-bet
EINECS 200-263-3
(3ar,4s,7r,7as)-3a,7a-dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione
2,3-dimethyl-7-oxa-bicyclo[2.2.1]heptane-2exo,3exo-dicarboxylic acid anhydride
(1R,2S,6R,7S)-2,6-Dimethyl-4,10-dioxatricyclo[5.2.1.0]decane-3,5-dione
2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid anhydride
Camptothecine

Biological Activity

[Description]:

Cantharidin, a natural toxin isolated from beetles in the families Meloidae and Oedemeridae, has been reported to be toxic to some pests, including the diamondback moth.IC50 value:Target:In vitro: A 48 h treatment of human erythrocytes with cantharidin significantly increased the percentage of annexin-V-binding cells (≥10 μg/mL), significantly decreased forward scatter (≥25 μg/mL), significantly increased [Ca2+]i (≥25 μg/mL), but did not significantly modify ceramide abundance or ROS [1]. In vivo:

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Others

[References]

[1]. Alzoubi K, et al. Induction of Suicidal Erythrocyte Death by Cantharidin. Toxins (Basel). 2015 Jul 28;7(8):2822-34.

[2]. Huang Z, et al. Lethal and Sublethal Effects of Cantharidin on Development and Reproduction of Plutella xylostella (Lepidoptera: Plutellidae). J Econ Entomol. 2015 Jun;108(3):1054-64.

[3]. Shen M, et al. Cantharidin represses invasion of pancreatic cancer cells through accelerated degradation of MMP2 mRNA. Sci Rep. 2015 Jul 2;5:11836.

[4]. Hsieh FS, et al. Inhibition of protein phosphatase 5 suppresses non-small cell lung cancer through AMP-activated kinase activation. Lung Cancer. 2017 Oct;112:81-89.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
326.9±35.0 °C at 760 mmHg

[ Melting Point ]:
215-217 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂O₄

[ Molecular Weight ]:
196.200

[ Flash Point ]:
146.1±26.0 °C

[ Exact Mass ]:
196.073563

[ PSA ]:
52.60000

[ LogP ]:
0.10

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.547

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RN8575000

CHEMICAL NAME :: 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, 2,3-dimethyl-

CAS REGISTRY NUMBER :: 56-25-7

BEILSTEIN REFERENCE NO. :: 0085302

LAST UPDATED :: 199701

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C10-H12-O4

MOLECULAR WEIGHT :: 196.22

WISWESSER LINE NOTATION :: T C555 A AO DVOVTJ C1 G1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 428 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 34ZIAG "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969 Volume(issue)/page/year: -,646,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 35,823,1987

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 310 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Cardiac - arrhythmias (including changes in conduction)

REFERENCE :: TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 23,36,1985

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 32 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 7273 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FDWU** "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931 Volume(issue)/page/year: -,-,1931

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1710 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85PEAG "Zhongliu Yanjiu" Cancer Review, Yu, R., et al., eds., Shanghai Science/Technology Publisher, Peop. Rep. China, 1994 Volume(issue)/page/year: -,183,1994

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 20,135,1989 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg/14W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors

REFERENCE :: BJCAAI British Journal of Cancer. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.1- 1947- Volume(issue)/page/year: 9,177,1955

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 70 mg/kg/52W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 32,1463,1972 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,79,1976 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,79,1976 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H315-H319-H335

[ Precautionary Statements ]:
Missing Phrase - N15.00950417-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+:Verytoxic;

[ Risk Phrases ]:
R28;R36/37/38

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
UN 2811 6.1/PG 1

[ WGK Germany ]:
3

[ RTECS ]:
RN8575000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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