Basic information
- CAS
31430-18-9- Standard SMILES
COC(=O)Nc1nc2ccc(C(=O)c3cccs3)cc2[nH]1- InChIKey
KYRVNWMVYQXFEU-UHFFFAOYSA-N- Molecular formula
- C14H11N3O3S
- Average molar mass
- 301.32 g/mol
- Monoisotopic mass
- 301.05211239
Overview
Nocodazole is a white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- Nocodazole
- IUPAC
- methyl N-[6-(thiophene-2-carbonyl)-1H-benzimidazol-2-yl]carbamate
- English name
- NOCODAZOLE
- Molecular formula
- C14H11N3O3S
- Molecular weight
- 301.32
Names & synonyms
nocodazole31430-18-9OncodazoleNocodazolNocodazolumR 17934NSC-238159NSC 238159R 17,934Methyl 5-(2-thenoyl)-2-benzimidazolecarbamateR-17934DTXSID9031800
Show more names
CS-2010NorcodazoleNocodazole,98%Nocodazole,99+%Nocodazole【M1404】
Methyl (5-(2-thienylcarbonyl))-1H-benzimidazole-2-ylcarbamateN-(5-(2-Thenoyl)-2-benzimidazolyl)carbamic acid methyl esterNSC238159R179342-Benzimidazolecarbamic acid, 5-(2-thenoyl)-, methyl esterNSC 238 159SH1WY3R615Methyl (5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl)carbamate
Database identifiers
- CAS
31430-18-9- PubChem CID
- 4122
- DTXSID
DTXSID9031800- ChEMBL
CHEMBL9514- ChEBI
CHEBI:34892- UNII
- SH1WY3R615
- EC Number
- 250-626-5
- Nikkaji
- J20.370J
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 420
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility
less than 1 mg/mL at 59 °F (NTP, 1992)
0.3 [ug/mL] (The mean of the results at pH 7.4)
Melting Point570 °F (decomposes) (NTP, 1992)
Physical DescriptionNocodazole is a white powder. (NTP, 1992)
Collision Cross Section
180.63 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
168.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 300 °C · 300 °C (dec.)
- Density
- 1.49 · 1.490
- refractive index
- 1.674 · 1.6740 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL, · DMSO: 10 mg/mL, soluble
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H341 (98.6%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 74 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of sulfur oxides and nitrogen oxides. (NTP, 1992)
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity ProfileNOCODAZOLE may be sensitive to heat. (NTP, 1992).
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesMuta. 2 (98.6%)
Safety & protection
Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
Applications
DescriptionNocodazole reversibly binds tubulin and alters tubulin-associated GTP hydrolysis as well as microtubule dynamics. While nocodazole is used to study many aspects on microtubule function, it is most commonly used to synchronize cell cycling in culture. Typically, nanomolar concentrations of nocodazole reduce both microtubule elongation and shortening velocities, resulting in arrest of cycling in a G2/M phase. Nocodazole is also used to induce the formation of Golgi ministacks in eukaryotic cells.
UsesAntineoplastic;Microtubule poison
UsesA potent Tubulin production inhibitor and anti-neoplastic agent
UsesNocodazole has been shown to enhance CRISPR genome editing efficiency. To see other small molecule CRISPR enhancers, visit sigma.com/CRISPR-enhancers.
UsesA synthetic chemotherapeutic agent with antineoplastic, antifungal and anthelmintic activities. Microtubule inhibitor; inhibits mitosis
General DescriptionWhite powder.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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