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=CC(=CC=C2N1)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 1076
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 8504		0.091 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12203371	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification and characterization of a family of Rab11-interacting proteins.	2001-10-19	11495908
Dual control of replication timing. Stochastic onset but programmed completion of mammalian chromosome duplication.	2001-09-28	11454865
Identification of novel bifunctional calmodulin-binding and microtubule-stabilizing motifs in STOP proteins.	2001-08-17	11413126
Movement of endoplasmic reticulum in the living axon is distinct from other membranous vesicles in its rate, form, and sensitivity to microtubule inhibitors.	2001-08-01	11494358
Mammalian Golgi-associated Bicaudal-D2 functions in the dynein-dynactin pathway by interacting with these complexes.	2001-08-01	11483508
Dioxin suppresses the checkpoint protein, MAD2, by an aryl hydrocarbon receptor-independent pathway.	2001-08-01	11479202
Inhibition of human immunodeficiency virus type 1 transcription by chemical cyclin-dependent kinase inhibitors.	2001-08	11461999
Dissolution of poorly crystalline apatite crystals by osteoclasts determined on artificial thin-film apatite.	2001-08	11340596
Insulin stimulates membrane conductance in a liver cell line: evidence for insertion of ion channels through a phosphoinositide 3-kinase-dependent mechanism.	2001-07-20	11349127
The mouse Mps1p-like kinase regulates centrosome duplication.	2001-07-13	11461705
Mps1 is a kinetochore-associated kinase essential for the vertebrate mitotic checkpoint.	2001-07-13	11461704
Microtubules are involved in glucose-dependent dissociation of the yeast vacuolar [H+]-ATPase in vivo.	2001-07-06	11331282
Variation in adenovirus receptor expression and adenovirus vector-mediated transgene expression at defined stages of the cell cycle.	2001-07	11472101
Aneuploid colon cancer cells have a robust spindle checkpoint.	2001-07	11454737
Translocation of active mitochondria during pig oocyte maturation, fertilization and early embryo development in vitro.	2001-07	11425340
Effect of cytokinesis inhibitors, DMSO and the timing of oocyte activation on mouse cloning using cumulus cell nuclei.	2001-07	11425329
Cytochalasin D induces edema formation and lowering of interstitial fluid pressure in rat dermis.	2001-07	11406462
Brefeldin A block of integrin-dependent mechanosensitive ATP release from Xenopus oocytes reveals a novel mechanism of mechanotransduction.	2001-06-29	11320093
Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest.	2001-06-28	11439342
Identification of a human orthologue of Sec34p as a component of the cis-Golgi vesicle tethering machinery.	2001-06-22	11292827
Hydrocarbon carcinogens evade cellular defense mechanism of G1 arrest in nontransformed and malignant lung cell lines.	2001-06-01	11384212
p53 displacement from centrosomes and p53-mediated G1 arrest following transient inhibition of the mitotic spindle.	2001-06-01	11376010
The Bub2-dependent mitotic pathway in yeast acts every cell cycle and regulates cytokinesis.	2001-06	11493673
The non-catalytic domain of the Xenopus laevis auroraA kinase localises the protein to the centrosome.	2001-06	11493645
Glucosylceramide synthesis inhibitors block pharmacologically induced dispersal of the Golgi and anterograde membrane flow from the endoplasmic reticulum: implication of sphingolipid metabolism in maintenance of the Golgi architecture and anterograde membrane flow.	2001-06	11471737
Endocytosis of NBD-sphingolipids in neurons: exclusion from degradative compartments and transport to the Golgi complex.	2001-06	11389767
Cytoplasmic changes in relation to nuclear maturation and early embryo developmental potential of porcine oocytes: effects of gonadotropins, cumulus cells, follicular size, and protein synthesis inhibition.	2001-06	11389554
Hypertonic activation of the renal betaine/GABA transporter is microtubule dependent.	2001-06	11380820
Roles of Ets proteins, NF-kappa B and nocodazole in regulating induction of transcription of mouse germline Ig alpha RNA by transforming growth factor-beta 1.	2001-06	11369700
Cell-specific basolateral membrane sorting of the human liver Na(+)-dependent bile acid cotransporter.	2001-06	11352825
Mutations in the mitotic check point gene, MAD1L1, in human cancers.	2001-05-31	11423979
Regulation of microtubule assembly by human EB1 family proteins.	2001-05-31	11423968
Negative regulation of G(1)/S transition by the candidate bladder tumour suppressor gene DBCCR1.	2001-05-24	11420708
DCX in PC12 cells: CREB-mediated transcription and neurite outgrowth.	2001-05-01	11331616
Caveolar endocytosis of simian virus 40 reveals a new two-step vesicular-transport pathway to the ER.	2001-05	11331875
Apoptosis can be a confusing factor in in vitro clastogenic assays.	2001-05	11320150
Involvement of nuclear factor kappaB in c-Myc induction by tubulin polymerization inhibitors.	2001-05	11306700
Endothelial microtubule disruption blocks flow-dependent dilation of arterioles.	2001-05	11299210
Asymmetrical segregation of chromosomes with a normal metaphase/anaphase checkpoint in polyploid megakaryocytes.	2001-04-15	11290584
Association of bovine papillomavirus type 1 with microtubules.	2001-04-10	11289806
Cytoskeletal reorganization during the formation of oligodendrocyte processes and branches.	2001-04	11312599
Determination of the net exchange rate of tubulin dimer in steady-state microtubules by fluorescence correlation spectroscopy.	2001-03	11347885
Functional integrity of the vesicle transporting machinery is required for complete activation of cFTR expressed in xenopus laevis oocytes.	2001-03	11316271
Growth arrest in A549 cells during hyperoxic stress is associated with decreased cyclin B1 and increased p21(Waf1/Cip1/Sdi1) levels.	2001-02-05	11341986
Nocodazole treatment of CV-1 cells enhances nuclear/perinuclear accumulation of lipid-DNA complexes and increases gene expression.	2001-02	11405299
Uptake of endocytic markers by rice cells: variations related to the growth phase.	2001-02	11302523
Mechanism of hyperploid cell formation induced by microtubule inhibiting drug in glioma cell lines.	2001-01-25	11313973
The effect of cytochalasin J on kinetochore structure in PtK1 cells is mitotic cycle dependent.	2001	11482906
Development of porcine embryos reconstituted with somatic cells and enucleated metaphase I and II oocytes matured in a protein-free medium.	2001	11476669
Microtubule-targeting drugs induce Bcl-2 phosphorylation and association with Pin1.	2000-11-06	11326318

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

NSC-238159

Preferred Name

English

NOCODAZOLE

Official Name

English

nocodazole [INN]

Common Name

English

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

Common Name

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