Nocodazole

Modify Date: 2025-08-25 08:27:11

Nocodazole Structure
Nocodazole structure
 Common Name Nocodazole
CAS Number 31430-18-9 Molecular Weight 301.320
Density 1.5±0.1 g/cm3 Boiling Point N/A
Molecular Formula C14H11N3O3S Melting Point 300 °C (dec.)
MSDS Chinese USA Flash Point N/A
Symbol GHS08
GHS08		 Signal Word Warning

 Use of Nocodazole


Nocodazole is a rapidly-reversible inhibitor of microtubule. Nocodazole binds to β-tubulin and disrupts microtubule assembly/disassembly dynamics, which prevents mitosis and induces apoptosis in tumor cells.

 Names

Name nocodazole
Synonym More Synonyms

 Nocodazole Biological Activity

Description Nocodazole is a rapidly-reversible inhibitor of microtubule. Nocodazole binds to β-tubulin and disrupts microtubule assembly/disassembly dynamics, which prevents mitosis and induces apoptosis in tumor cells.
Related Catalog
Target

Abl:91 nM (Kd)

ABL(E255K):120 nM (Kd)

ABL(T315I):170 nM (Kd)

BRAF:1.8 μM (Kd)

BRAF(V600E):1.1 μM (Kd)

c-KIT:1.6 μM (Kd)

MEK1:1.7 μM (Kd)

MEK2:1.6 μM (Kd)

MET:1.7 μM (Kd)

PI3Kγ:1.5 μM (Kd)

Microtubule/Tubulin

CRISPR/Cas9

In Vitro Nocodazole exhibits good affinity toward c-KIT, with a Kd value of 1.6 μM in highly malignant human cancer cells. Nocodazole displays good binding affinity toward the components of the mitogen-activated protein kinase (MAPK) pathway, such as BRAF (Kd=1.8 μM), BRAF(V600E) (Kd=1.1 μM), MEK1 (Kd=1.7 μM), and MEK2 (Kd=1.6 μM)[1]. Nocodazole has the highest affinity for αβIV and the lowest affinity for αβIII[2]. After release from the nocodazole block, cells synchronized in mitosis remaine sensitive to very low concentrations of paclitaxel for < 30 min, the time required for spindle formation, yet remains sensitive to vinblastine for > 90 min[3]. Nocodazole (1 nM) induces apoptosis of COLO 205 cancer cells[4]. Nocodazole (≥ 30 µg/mL) significantly increases the percentage of annexin-V-binding cells without significantly modifying average forward scatter of human erythrocytes[5].
In Vivo Nocodazole (5 mg/kg/three times per week, i.p.) has antitumor effects in athymic mice bearing COLO 205 tumor xenografts. Nocodazole (1 nM) + ketoconazole dramatically increase the levels of p21/CIP1 and p27/KIP1 protein in the tumor tissues[4].
Cell Assay Proteins are loaded at 50 μg/lane and separated by 12% (w:v) sodium dodecyl sulfate-polyacrylamide gel electrophoresis, blotted, and probed with antibodies for cyclin E, p53, p21/CIP1, p27/KIP1, glyceraldehyde 3-phosphate dehydrogenase (GAPDH), cyclin A, cyclin D1, cyclin D3, cyclin B, CDK2, CDK4, and cytochrome C. Immunoreactive bands are visualized by incubating with the colorigenic substrates nitroblue tetrazolium and 5-bromo-4-chloro-3-indolyl-phosphate. The expression of GAPDH is used as the control for equal protein loading.
Animal Admin COLO 205 cells are grown in RPMI 1640 supplemented with 10% FCS. Cells are harvested through two consecutive trypsinizations, centrifuged at 300×g; for 5 min, washed twice, and resuspended in sterile phosphate-buffered saline (PBS). Cells (5×105) in 0.1 mL are injected subcutaneously between the scapulae of each nude mouse. After transplantation, tumor size is measured with calipers, and the tumor volume is estimated. Once tumors reach a mean size of 200 mm3, animals receive intraperitoneal injections of DMSO (25 μL), ketoconazole (50 mg/kg), nocodazole (5 mg/kg), or ketoconazole + nocodazole three times per week for 6 wk.
References

[1]. Park H, et al. Nocodazole is a high-affinity ligand for the cancer-related kinases ABL, c-KIT, BRAF, and MEK. ChemMedChem. 2012 Jan 2;7(1):53-6.

[2]. Keliang Xu, et al. Interaction of nocodazole with tubulin isotypes. Drug Development Research 2002

[3]. Long BH, et al. Paclitaxel inhibits progression of mitotic cells to G1 phase by interference with spindle formation without affecting other microtubule functions during anaphase and telephase. Cancer Res. 1994 Aug 15;54(16):4355-61.

[4]. Wang YJ, et al. Ketoconazole potentiates the antitumor effects of nocodazole: In vivo therapy for human tumor xenografts in nude mice. Mol Carcinog. 2002 Aug;34(4):199-210.

[5]. Signoretto E, et al. Nocodazole Induced Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2016;38(1):379-92.

[6]. Zhang JP, et al. Efficient precise knockin with a double cut HDR donor after CRISPR/Cas9-mediated double-stranded DNA cleavage. Genome Biol. 2017 Feb 20;18(1):35.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Melting Point 300 °C (dec.)
Molecular Formula C14H11N3O3S
Molecular Weight 301.320
Exact Mass 301.052124
PSA 112.32000
LogP 2.43
Index of Refraction 1.732
Storage condition 2-8°C
Water Solubility DMSO: 10 mg/mL, soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DD6521000
CHEMICAL NAME :
2-Benzimidazolecarbamic acid, 5-(2-thenoyl)-, methyl ester
CAS REGISTRY NUMBER :
31430-18-9
LAST UPDATED :
199606
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C14-H11-N3-O3-S
MOLECULAR WEIGHT :
301.34
WISWESSER LINE NOTATION :
T56 BM DNJ CMVO1 GV- BT5SJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
39530 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
10 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Sex chromosome loss and nondisjunction

MUTATION DATA

TYPE OF TEST :
Sex chromosome loss and nondisjunction
TEST SYSTEM :
Mammal - species unspecified
DOSE/DURATION :
2 ug/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 201,423,1988

 Safety Information

Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H341-H361d
Precautionary Statements P281
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes T: Toxic;
Risk Phrases R61
Safety Phrases S53-S45-S36/37/39-S26
RIDADR 2811
WGK Germany 3
RTECS DD6521000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2934999090

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

2-Benzimidazolecarbamic acid, 5-(2-thienylcarbonyl)-, methyl ester
Methyl N-(5-thenoyl-2-benzimidazolyl)carbamate
methyl N-[6-(thiophene-2-carbonyl)-1H-benzimidazol-2-yl]carbamate
Methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate
Nocodazole
Nocidazole
2-Benzimidazolecarbamic acid, 5-(2-thienoyl)-, methyl ester
Methyl 5-(2-thienoyl)-2-benzimidazolecarbamate
nocodazolum
Nocodazol
methyl [5-(thiophen-2-ylcarbonyl)-1H-benzimidazol-2-yl]carbamate
EINECS 250-626-5
Carbamic acid, N-[5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]-, methyl ester
Oncodazole
MFCD00005588
methyl 5-(thiophene-2-carbonyl)-1H-benzo[d]imidazol-2-ylcarbamate
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