WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206212
Description: Carbendazim is a widely used, broad-spectrum benzimidazole fungicide and a metabolite of benomyl. It is also employed as a casting worm control agent in amenity turf situations such as golf greens, tennis courts etc. and in some countries is licensed for that use only. The fungicide is used to control plant diseases in cereals and fruits, including citrus, bananas, strawberries, pineapples, and pomes. It is also controversially used in Queensland, Australia on macadamia plantations. A 4.7% solution of carbendazim hydrochloride, sold as Eertavas, is marketed as a treatment for Dutch elm disease. Studies have found high doses of carbendazim cause infertility and destroy the testicles of laboratory animals. Maximum pesticide residue limits (MRLs) have reduced since discovering its harmful effects. The MRLs for fresh produce in the EU are now between 0.1 and 0.7 mg/kg with the exception of loquat, which is 2 mg/kg. The limits for more commonly consumed citrus and pomme fruits are between 0.1 and 0.2 mg/kg.
MedKoo Cat#: 206212
Chemical Formula: C9H9N3O2
Exact Mass: 191.06948
Molecular Weight: 191.19
Elemental Analysis: C, 56.54; H, 4.74; N, 21.98; O, 16.74
Synonym: Mercarzole; Carbendazole. Code name: FB462.
IUPAC/Chemical Name: methyl 1H-benzo[d]imidazol-2-ylcarbamate
InChi Key: TWFZGCMQGLPBSX-UHFFFAOYSA-N
InChi Code: InChI=1S/C9H9N3O2/c1-14-9(13)12-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H2,10,11,12,13)
SMILES Code: O=C(OC)NC1=NC2=CC=CC=C2N1
Carbendazim is a widely used broad-spectrum benzimidazole fungicide. A 4.7% solution of carbendazim hydrochloride is sold as Eertavas, an effective treatment for Dutch elm disease. Carbendazim was included in a biocide ban proposed by the Swedish Chemicals Agency and approved by the European Parliament in January 13, 2009. The fungicide is controversially used in Queensland, Australia on macadamia plantations.
Carbendazim is also an anticancer drug candidate, currently being investigated by AmpliMed. It also inhibits proliferation of human cancer cells, including drug- and multidrug-resistant and p53-deficient cell lines. Because of its promising preclinical anti-tumor activity, it has undergone phase I clinical trials and is under further clinical development. Carbendazim inhibits proliferation (IC50, 10 μM) of MCF7 human breast cancer cells and half-maximally arrests mitosis at a similar concentration (8 μM), in concert with suppression of microtubule dynamic instability without appreciable microtubule depolymerization. It induces mitotic spindle abnormalities and reduces the metaphase intercentromere distance of sister chromatids, indicating reduction of tension on kinetochores, thus leading to metaphase arrest. With microtubules assembled in vitro from pure tubulin, carbendazim also suppresses dynamic instability, reducing the dynamicity by 50% at 10 μM, with only minimal (21%) reduction of polymer mass. Carbendazim binds to mammalian tubulin (Kd, 42.8 Â± 4.0 μM). Unlike some benzimidazoles that bind to the colchicine site in tubulin, carbendazim neither competes with colchicine nor competes with vinblastine for binding to brain tubulin. Thus, carbendazim binds to an as yet unidentified site in tubulin and inhibits tumor cell proliferation by suppressing the growing and shortening phases of microtubule dynamic instability, thus inducing mitotic arrest. (source: Yenjerla M, Cox C, Wilson L, Jordan MA. Carbendazim inhibits cancer cell proliferation by suppressing microtubule dynamics. J Pharmacol Exp Ther. 2009 Feb;328(2):390-8. Epub 2008 Nov 10.
Current developer: AmpliMed.
1: ClÃ©ment MJ, Rathinasamy K, Adjadj E, Toma F, Curmi PA, Panda D. Benomyl and colchicine synergistically inhibit cell proliferation and mitosis: evidence of distinct binding sites for these agents in tubulin. Biochemistry. 2008 Dec 9;47(49):13016-25. PubMed PMID: 19049291.
2: Yenjerla M, Cox C, Wilson L, Jordan MA. Carbendazim inhibits cancer cell proliferation by suppressing microtubule dynamics. J Pharmacol Exp Ther. 2009 Feb;328(2):390-8. Epub 2008 Nov 10. PubMed PMID: 19001156; PubMed Central PMCID: PMC2682274.
3: Fellows MD, O'Donovan MR. Cytotoxicity in cultured mammalian cells is a function of the method used to estimate it. Mutagenesis. 2007 Jul;22(4):275-80. Epub 2007 Apr 24. PubMed PMID: 17456508.
4: Carazo-Salas RE, Antony C, Nurse P. The kinesin Klp2 mediates polarization of interphase microtubules in fission yeast. Science. 2005 Jul 8;309(5732):297-300. PubMed PMID: 16002618.
5: Pardo M, Nurse P. Equatorial retention of the contractile actin ring by microtubules during cytokinesis. Science. 2003 Jun 6;300(5625):1569-74. PubMed PMID: 12791993.
6: McCarroll NE, Protzel A, Ioannou Y, Frank Stack HF, Jackson MA, Waters MD, Dearfield KL. A survey of EPA/OPP and open literature on selected pesticide chemicals. III. Mutagenicity and carcinogenicity of benomyl and carbendazim. Mutat Res. 2002 Sep;512(1):1-35. Review. PubMed PMID: 12220588