An inhibitor of microtubule polymerization and an anthelmintic
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Labeled Version(s)
40232Mebendazole-d8
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Mebendazole

Item No. 18872

Technical Information
Formal Name
N-(6-benzoyl-1H-benzimidazol-2-yl)-carbamic acid, methyl ester
CAS Number
31431-39-7
Synonyms
  • NSC 184849
  • R 17635
Molecular Formula
C16H13N3O3
Formula Weight
Purity
≥98%
A crystalline solid
DMSO: to 10 mM
λmax
209, 246, 310 nm
SMILES
O=C(C1=CC=C(NC(NC(OC)=O)=N2)C2=C1)C3=CC=CC=C3
InChi Code
InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)
InChi Key
OPXLLQIJSORQAM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Mebendazole is an inhibitor of microtubule polymerization and an anthelmintic.1 It reduces microtubule polymerization in a cell-free assay when used at a concentration of 10 µM. Mebendazole reduces container attachment, a measure of viability, by G. duodenalis with a half-maximal inhibition of binding (IB50) value of 190 nM.2 It reduces the proliferation of SK-MEL-19 and M14 melanoma cell lines (IC50s = 300 and 320 µM, respectively) and induces apoptosis and poly(ADP-ribose) polymerase (PARP) cleavage in SK-MEL-19 and M14 cells, but not melanocytes, when used at a concentration of 1 µM.3 It decreases oxidative stress-induced cell death in primary mouse cortical neurons in a concentration-dependent manner.1 In vivo, mebendazole (800 µg/animal every other day) decreases tumor volume, weight, hemoglobin levels, and vascularization in an H460 lung cancer mouse xenograft model.4 Mebendazole (8.8 mg/kg) eradicates S. vulgaris, S. edentates, and S. equinus worm burden in infected ponies.5 Formulations containing mebendazole have been used in the treatment of helminth gastrointestinal infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aleyasin, H., Karuppagounder, S.S., Kumar, A., et alAntihelminthic benzimidazoles are novel HIF activators that prevent oxidative neuronal death via binding to tubulin. Antioxid. Redox Signal. 22(2), 121-134 (2015).

    2. Morgan, U.M., Reynoldson, J.A., and Thompson, R.C.A. Activities of several benzimidazoles and tubulin inhibitors against Giardia spp. in vitro. Antimicrob. Agents Chemother. 37(2), 328-331 (1993).

    3. Doudican, N., Rodriguez, A., Osman, I., et alMebendazole induces apoptosis via Bcl-2 inactivation in chemoresistant melanoma cells. Mol. Cancer Res. 6(8), 1308-1315 (2008).

    4. Mukhopadhyay, T., Sasaki, J.i., Ramesh, R., et alMebendazole elicits a potent antitumor effect on human cancer cell lines both in vitro and in vivo. Clin. Cancer Res. 8(9), 2963-2969 (2002).

    5. Colglazier, M.L., Enzie, F.D., and Kates, K.C. Critical anthelmintic trials in ponies with four benzimidazoles: Mebendazole, cambendazole, fenbendazole, and albendazole. J. Parasitol. 63(4), 724-727 (1977).