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{{more citations needed|date=November 2016}}

{{Short description|Microtubule depolymerizing drug}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 405910037
| Name = Nocodazole
| ImageFile = Nocodazole structure.svg
| ImageClass = skin-invert-image
| IUPACName = Methyl [5-(2-thienylcarbonyl)-1''H''-benzimidazol-2-yl]carbamate

| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = SH1WY3R615
| SMILES = O=C(C2=CC=CS2)C1=CC=C(N=C(NC(OC)=O)N3)C3=C1
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 31430-18-9
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 9514
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 34892
| EINECS = 250-626-5
| PubChem = 4122
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 3979
| 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)
| InChIKey = KYRVNWMVYQXFEU-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = KYRVNWMVYQXFEU-UHFFFAOYSA-N
| RTECS =
| MeSHName =
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C13719
}}

| Section2 = {{Chembox Properties
| C = 14 | H = 11 | N = 3 | O = 3 | S = 1
| Appearance = White with faint yellow cast powder
| Solubility = Approximately 10 mg/mL in DMSO
| MeltingPtC = 256
}}
}}

'''Nocodazole''' is an [[antineoplastic agent]] which exerts its effect in cells by interfering with the [[polymer]]ization of [[microtubule]]s.<ref>{{cite journal|title=The microtubule depolymerizing drugs nocodazole and colchicine inhibit the uptake of Listeria monocytogenes by P388D1 macrophages|journal=FEMS Microbiology Letters|volume= 160|issue= 1|date=17 January 2006|first1=Michael |last1=Kuhn|pages=87–90|doi=10.1111/j.1574-6968.1998.tb12895.x|doi-access=free|pmid=9495017}}</ref><ref>{{Cite journal | vauthors = Baksheeva VE, La Rocca R, Allegro D, Derviaux C, Pasquier E, Roche P, Morelli X, Devred F, Golovin AV, Tsvetkov PO | title = NanoDSF Screening for Anti-tubulin Agents Uncovers New Structure–Activity Insights | journal = Journal of Medicinal Chemistry | date = 2025 | doi = 10.1021/acs.jmedchem.5c01008 }}</ref> 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]].<ref>{{Cite journal|title = LATS2 suppresses oncogenic Wnt signaling by disrupting β-catenin/BCL9 interaction|journal = Cell Reports|date = 2013-12-26|issn = 2211-1247|pmc = 3897473|pmid = 24360964|pages = 1650–1663|volume = 5|issue = 6|doi = 10.1016/j.celrep.2013.11.037|first = Jiong|last = Li|first2 = Xiaohong|last2 = Chen|first3 = Xiangming|last3 = Ding|first4 = Yingduan|last4 = Cheng|first5 = Bin|last5 = Zhao|first6 = Zhi-Chun|last6 = Lai|first7 = Khalid|last7 = Al Hezaimi|first8 = Razqallah|last8 = Hakem|first9 = Kun-Liang|last9 = Guan|authorlink9=Kun-Liang Guan}}</ref>

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

==Use in cell biology research==
{{citations needed|section|date=April 2025}}
As nocodazole affects the cytoskeleton, it is often used in [[cell biology]] experiments as a control: for example, some dominant negative [[Rho family of GTPases|Rho]] [[small GTPase]]s cause a similar effect as nocodazole, and constitutively activated mutants often reverse or negate the effect.

Nocodazole is frequently used in cell biology laboratories to synchronize the [[cell cycle|cell division cycle]]. Cells treated with nocodazole arrest with a [[G2 phase|G2]]- or [[Mitosis|M]]-phase DNA content when analyzed by [[flow cytometry]]. Microscopy of nocodazole-treated cells shows that they do enter [[mitosis]] but cannot form [[metaphase]] [[mitotic spindle|spindles]] because microtubules (of which the spindles are made) cannot polymerise. The absence of microtubule attachment to [[kinetochore]]s activates the [[spindle checkpoint|spindle assembly checkpoint]], causing the cell to arrest in [[prometaphase]]. For cell synchronization experiments, nocodazole is usually used at a concentration of 40–100 ng/mL of culture medium for a duration of 12–18 hours. Prolonged arrest of cells in mitosis due to nocodazole treatment typically results in cell death by [[apoptosis]].

Another standard cell biological application of nocodazole is to induce the formation of Golgi ministacks in [[eukaryotic]] cells. The perinuclear structural organization of the [[Golgi apparatus]] in eukaryotes is dependent on microtubule trafficking, but disrupting the trafficking of Golgi elements from the endoplasmic reticulum treatment with nocodazole (33 μM for 3 hours) induces numerous Golgi elements to form adjacent to ER exit sites{{Citation needed|date=October 2025}}. These functional Golgi ministacks remain distributed about the cell, unable to track forward to form a perinuclear Golgi since nocodazole has depolymerized the microtubules.

Also used with Mad2p protein as an anti-microtubule drug.

==See also==

* [[Colchicine]]

==References==
{{reflist}}

{{Portal bar | Medicine}}
{{chemotherapeutic agents}}

[[Category:Antineoplastic drugs]]
[[Category:Benzimidazoles]]
[[Category:Carbamates]]
[[Category:Cell biology]]
[[Category:Microtubule inhibitors]]
[[Category:Thiophenes]]
[[Category:Methyl esters]]

Nocodazole - Revision history

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