Skip to Content
Merck
CN
All Photos(4)

Documents

M1404

Sigma-Aldrich

Nocodazole

≥99% (TLC), powder

Synonym(s):

Methyl N-(5-thenoyl-2-benzimidazolyl)carbamate, Methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate, Oncodazole, R 17934, [5-(2-Thienylcarbonyl)-1H-benzimidazol-2-yl]-carbamic acid methyl ester

Sign Into View Organizational & Contract Pricing
All Photos(4)

About This Item

Empirical Formula (Hill Notation):
C14H11N3O3S
CAS Number:
31430-18-9
Molecular Weight:
301.32
Beilstein:
1085978
EC Number:
250-626-5
MDL number:
MFCD00005588
UNSPSC Code:
12352200
PubChem Substance ID:
24278535
NACRES:
NA.77

Quality Level

300

Assay

≥99% (TLC)

form

powder

mp

300 °C (dec.)

solubility

DMSO: soluble 10 mg/mL (may require heating)
H2O: insoluble

storage temp.

2-8°C

SMILES string

COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c3cccs3

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)

InChI key

KYRVNWMVYQXFEU-UHFFFAOYSA-N

Gene Information

human ... TUBB(203068)

Looking for similar products? Visit Product Comparison Guide

General description

Nocodazole (NZO) is an experimental benzimidazole-based agent that targets both protein kinases and microtubules. It serves as a lead compound in the quest for new colchicine binding site inhibitors (CBSIs). This co-crystallized ligand acts as a high-affinity ligand for cancer-related kinases ABL, c-KIT, BRAF, and MEK, and functions as a rapidly-reversible inhibitor of microtubule polymerization.

Application

Nocodazole has been used to induce microtubule depolymerization in mouse melanoma B16-F1 cells. It has also been used to treat A549 cells for mitotic arrest.

Biochem/physiol Actions

Nocodazole is an antimitotic agent that disrupts microtubules by binding to β−tubulin and preventing formation of one of the two interchain disulfide linkages, thus inhibiting microtubule dynamics, disruption of mitotic spindle function, and fragmentation of the Golgi complex. Nocodazole arrests the cell cycle at G2/M phase and also prevents phosphorylation of the T cell antigen receptor and inhibits its activity. Nocodazole stimulates the intrinsic GTPase activity of tubulin and activates the JNK/SAPK signaling pathway and induces apoptosis in several normal and tumor cell lines. Nocodazole has been shown to enhance CRISPR homology-directed repair (HDR) efficiency and increase Cas9-mediated editing frequencies.

Physical form

Color white to faint yellow and pink

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H341,H361d

Hazard Classifications

Muta. 2 - Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Muralidharan Mani et al.
Biochimica et biophysica acta. Molecular cell research, 1866(9), 1463-1474 (2019-06-15)
The perinuclear stacks of the Golgi apparatus maintained by dynamic microtubules are essential for cell migration. Activation of Akt (protein kinase B, PKB) negatively regulates glycogen synthase kinase 3β (GSK3β)-mediated tau phosphorylation, which enhances tau binding to microtubules and microtubule
Microtubule dynamics alter the interphase nucleus
Gerlitz G, et al.
Cellular and Molecular Life Sciences, 70, 1255-1268 (2013)
Yuxi Wang et al.
The FEBS journal, 283(1), 102-111 (2015-10-16)
Microtubules are dynamic assemblies of αβ-tubulin heterodimers and have been recognized as highly attractive targets for cancer chemotherapy. A broad range of agents bind to tubulin and interfere with microtubule assembly. Despite having a long history of characterization, colchicine binding
Yuanming Cheng et al.
Cell reports, 28(7), 1703-1716 (2019-08-15)
Stem cells balance cellular fates through asymmetric and symmetric divisions in order to self-renew or to generate downstream progenitors. Symmetric commitment divisions in stem cells are required for rapid regeneration during tissue damage and stress. The control of symmetric commitment remains
Revisiting activity of some nocodazole analogues as a potential anticancer drugs using molecular docking and DFT calculations
Khattab M and Al-Karmalawy AA
Frontiers in Chemistry, 9, 628398-628398 (2021)
View All Related Papers

Articles

Small Molecule CRISPR Enhancers

Modulation of homology-directed repair (HDR) within the context of CRISPR-genome editing has led to the identification of small molecules that enhance CRISPR-mediated HDR efficiency in various cell types.

Fluorescent Live Cell Imaging of Cytoskeleton Structure Proteins using LentiBrite™ Lentiviral Biosensors

High titer lentiviral particles including beta-actin, alpha-tubulin and vimentin used for live cell analysis of cytoskeleton structure proteins.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service