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
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
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 ± 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.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
191.19
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Clément 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
