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
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)
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 |
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Target ID: CHEMBL2095182 |
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Target ID: P00519 Gene ID: 25.0 Gene Symbol: ABL1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22002881 |
0.091 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Uptake of pp65 in in vitro generated pp65-positive polymorphonuclear cells mediated by phagocytosis and cell fusion? | 2001 |
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Induction of cortical oscillations in spreading cells by depolymerization of microtubules. | 2001 Apr |
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Membrane-targeted green fluorescent protein reliably and uniquely marks cells through apoptotic death. | 2001 Apr 1 |
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Identification of novel bifunctional calmodulin-binding and microtubule-stabilizing motifs in STOP proteins. | 2001 Aug 17 |
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Nocodazole treatment of CV-1 cells enhances nuclear/perinuclear accumulation of lipid-DNA complexes and increases gene expression. | 2001 Feb |
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MCM3AP, a novel acetyltransferase that acetylates replication protein MCM3. | 2001 Feb |
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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 |
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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 |
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MAD2 haplo-insufficiency causes premature anaphase and chromosome instability in mammalian cells. | 2001 Jan 18 |
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Translocation of active mitochondria during pig oocyte maturation, fertilization and early embryo development in vitro. | 2001 Jul |
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The mouse Mps1p-like kinase regulates centrosome duplication. | 2001 Jul 13 |
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Microtubule integrity regulates Pak leading to Ras-independent activation of Raf-1. insights into mechanisms of Raf-1 activation. | 2001 Jul 6 |
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Identification of a human orthologue of Sec34p as a component of the cis-Golgi vesicle tethering machinery. | 2001 Jun 22 |
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Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest. | 2001 Jun 28 |
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The role of actin filaments and microtubules in hepatocyte spheroid self-assembly. | 2001 Mar |
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Apoptosis can be a confusing factor in in vitro clastogenic assays. | 2001 May |
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Involvement of nuclear factor kappaB in c-Myc induction by tubulin polymerization inhibitors. | 2001 May |
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DCX in PC12 cells: CREB-mediated transcription and neurite outgrowth. | 2001 May 1 |
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Mutations in the mitotic check point gene, MAD1L1, in human cancers. | 2001 May 31 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12203371
tumor xenografts mice: 5 mg/kg/three times per week
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24360964
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.
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C250
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C25974
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ACTIVE MOIETY