NOCODAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H11N3O3S
Molecular Weight	301.32
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)NC1=NC2=C(N1)C=CC(=C2)C(=O)C3=CC=CS3

InChI

InChIKey=KYRVNWMVYQXFEU-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: DOI: 10.1002/ddr.10023 retrieved from http://onlinelibrary.wiley.com/doi/10.1002/ddr.10023/abstract | https://www.ncbi.nlm.nih.gov/pubmed/12203371 | https://www.ncbi.nlm.nih.gov/pubmed/22002881

Nocodazole is an anti-mitotic drug that has long been used as an experimental tool in cell biology. Nocodazole is known to bind with high affinity to tubulin and to inhibit microtubule assembly. The tubulin molecule is a α/β heterodimer; both α and β exist as various isotypes whose distribution and drug-binding properties are significantly different. Nocodazole has the highest affinity for αβIV and the lowest affinity for αβIII. In addition, nocodazole was investigated as an anticancer drug on xenografts model and it was revealed, that nocodazole possessed a high-affinity for the cancer-related kinases ABL, c-KIT, BRAF, and MEK, and inhibited Abl, Abl(E255K) and Abl(T315I).

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: DOI: 10.1002/ddr.10023 retrieved from http://onlinelibrary.wiley.com/doi/10.1002/ddr.10023/abstract	Binding Agent 1064
Tyrosine-protein kinase ABL1 7 Target ID: P00519 Gene ID: 25.0 Gene Symbol: ABL1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22002881	Inhibitor 8297		0.091 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12203371	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Uptake of pp65 in in vitro generated pp65-positive polymorphonuclear cells mediated by phagocytosis and cell fusion?	2001	11223714
Induction of cortical oscillations in spreading cells by depolymerization of microtubules.	2001 Apr	11276073
Membrane-targeted green fluorescent protein reliably and uniquely marks cells through apoptotic death.	2001 Apr 1	11260594
Identification of novel bifunctional calmodulin-binding and microtubule-stabilizing motifs in STOP proteins.	2001 Aug 17	11413126
Nocodazole treatment of CV-1 cells enhances nuclear/perinuclear accumulation of lipid-DNA complexes and increases gene expression.	2001 Feb	11405299
MCM3AP, a novel acetyltransferase that acetylates replication protein MCM3.	2001 Feb	11258703
Protein kinase C activation by 12-0-tetradecanoylphorbol 13-acetate in CG-4 line oligodendrocytes stimulates turnover of choline and ethanolamine phospholipids by phospholipase D and induces rapid process contraction.	2001 Jan	11208899
Carboxymethylation of the PP2A catalytic subunit in Saccharomyces cerevisiae is required for efficient interaction with the B-type subunits Cdc55p and Rts1p.	2001 Jan 12	11038366
MAD2 haplo-insufficiency causes premature anaphase and chromosome instability in mammalian cells.	2001 Jan 18	11201745
Translocation of active mitochondria during pig oocyte maturation, fertilization and early embryo development in vitro.	2001 Jul	11425340
The mouse Mps1p-like kinase regulates centrosome duplication.	2001 Jul 13	11461705
Microtubule integrity regulates Pak leading to Ras-independent activation of Raf-1. insights into mechanisms of Raf-1 activation.	2001 Jul 6	11274179
Identification of a human orthologue of Sec34p as a component of the cis-Golgi vesicle tethering machinery.	2001 Jun 22	11292827
Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest.	2001 Jun 28	11439342
The role of actin filaments and microtubules in hepatocyte spheroid self-assembly.	2001 Mar	11223949
Apoptosis can be a confusing factor in in vitro clastogenic assays.	2001 May	11320150
Involvement of nuclear factor kappaB in c-Myc induction by tubulin polymerization inhibitors.	2001 May	11306700
DCX in PC12 cells: CREB-mediated transcription and neurite outgrowth.	2001 May 1	11331616
Mutations in the mitotic check point gene, MAD1L1, in human cancers.	2001 May 31	11423979

Patents

Sample Use Guides

In Vivo Use Guide

tumor xenografts mice: 5 mg/kg/three times per week

Route of Administration: Oral

In Vitro Use Guide

Nocodazole potently induced LATS2 expression in HEK293T cells. Consistently, nocodazole significantly inhibited β-catenin-mediated transcription induced by LiCl or β-Cat overexpression. There also were found that nocodazole induced LATS2, but not LATS1, in a time-dependent manner in HCT116 cells and SW480 cells. While nocodazole significantly suppressed the expression of AXIN2 and MMP7 in HCT116 cells expressing scramble shRNA (HCT116/Scrsh), it could not affect the expression of AXIN2 and MMP7 in HCT116 cells expressing LATS2 shRNA (HCT116/LATS2sh). The restoration of LATS2 or LATS2N in HCT116/LATS2sh cells suppressed the expression of AXIN2 and MMP7, confirming the specificity of LATS2 shRNA. Moreover, ChIP assays found that nocodazole induced LATS2 binding to the promoter of AXIN2 or MMP7 in HCT116/Scrsh cells, but not in HCT116/LATS2sh cells. Consistently, was found that the occupancy of BCL9 on the promoter of AXIN2 or MMP7 was reduced in HCT116/Scrch cells, but not in HCT116/LATS2sh cells, upon nocodazole treatment. In contrast, nocodazole did not interfere with β-catenin presence on the promoter of AXIN2 or MMP7. The constitutive activation of Wnt/β-catenin plays a critical role in human colorectal tumor growth.

Name

Type

Language

NOCODAZOLE

Official Name

English

nocodazole [INN]

Common Name

English

Methyl 5-(2-thenoyl)-2-benzimidazolecarbamate

Common Name

English

NSC-238159

Code

English

NOCODAZOLE [USAN]

Common Name

English

R-17934

Code

English

R 17,934

Code

English

CARBAMIC ACID, (5-(2-THIENYLCARBONYL)-1H-BENZIMIDAZOLE-2-YL)-, METHYL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C250