Nocodazole

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Nocodazole
Names
IUPAC name
Methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.008 Edit this at Wikidata
EC Number
  • 250-626-5
KEGG
UNII
  • InChI=1S/C14H11N3O3S/c1-20-14(19)17-13-15-9-5-4-8(7-10(9)16-13)12(18)11-3-2-6-21-11/h2-7H,1H3,(H2,15,16,17,19) ☒N
    Key: KYRVNWMVYQXFEU-UHFFFAOYSA-N ☒N
  • InChI=1/C14H11N3O3S/c1-20-14(19)17-13-15-9-5-4-8(7-10(9)16-13)12(18)11-3-2-6-21-11/h2-7H,1H3,(H2,15,16,17,19)
    Key: KYRVNWMVYQXFEU-UHFFFAOYAF
  • O=C(C2=CC=CS2)C1=CC=C(N=C(NC(OC)=O)N3)C3=C1
Properties
C14H11N3O3S
Molar mass 301.32 g·mol−1
Appearance White with faint yellow cast powder
Melting point 256 °C (493 °F; 529 K)
Approximately 10 mg/mL in DMSO
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Nocodazole is an antineoplastic agent which exerts its effect in cells by interfering with the polymerization of microtubules.[1][2] Microtubules are one type of fibre which constitutes the cytoskeleton, and the dynamic microtubule network has several important roles in the cell, including vesicular transport, forming the mitotic spindle and in cytokinesis. Several drugs including vincristine and colcemid are similar to nocodazole in that they interfere with microtubule polymerization.

Nocodazole has been shown to decrease the oncogenic potential of cancer cells via another microtubules-independent mechanisms. Nocodazole stimulates the expression of LATS2 which potently inhibits the Wnt signaling pathway by abrogating the interaction between the Wnt-dependent transcriptional co-factors beta-catenin and BCL9.[3]

It is related to mebendazole by replacement of the left most benzene ring by thiophene.

See also

References

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