nocodazole (CHEBI:34892)

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ChEBI Name	nocodazole

ChEBI ID	CHEBI:34892

Definition	A member of the class of benzimidazoles that is benzimidalole which is substituted at position 2 by a (methoxycarbonyl)amino group and at position 5 by a 2-thienoyl group. It is an antineoplastic agent that exerts its effect by depolymerising microtubules.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB5338946, eMolecules:515191

Download	Molfile XML SDF

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Wikipedia	License
Muscimol (also known as agarin or pantherine) is the principal psychoactive constituent of Amanita muscaria and Amanita pantherina. Muscimol is a potent and selective orthosteric agonist for the GABAA receptor and displays sedative-hypnotic, depressant and hallucinogenic psychoactivity. This colorless or white solid is classified as an isoxazole. Muscimol underwent a phase I clinical trial for epilepsy, but drug development was discontinued. Muscimol, an agonist for the GABAA receptor, was able to significantly alleviate pain in its peak effect, recent studies from 2023 show. It has since been federally banned in Australia and is pending FDA review in the United States, but scientists believe it may relieve pain as well as some opioids without much of the risk of addiction associated with opioids.
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Formula

C14H11N3O3S

Net Charge

Average Mass

301.32000

Monoisotopic Mass

301.05211

InChI

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)

InChIKey

KYRVNWMVYQXFEU-UHFFFAOYSA-N

SMILES

COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c1cccs1

Roles Classification
Biological Role(s):	tubulin modulator Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules. antimitotic Any compound that inhibits cell division (mitosis). microtubule-destabilising agent Any substance that interacts with tubulin to inhibit polymerisation of microtubules.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	nocodazole (CHEBI:34892) has role antimitotic (CHEBI:64911) nocodazole (CHEBI:34892) has role antineoplastic agent (CHEBI:35610) nocodazole (CHEBI:34892) has role microtubule-destabilising agent (CHEBI:61951) nocodazole (CHEBI:34892) has role tubulin modulator (CHEBI:60832) nocodazole (CHEBI:34892) is a aromatic ketone (CHEBI:76224) nocodazole (CHEBI:34892) is a benzimidazoles (CHEBI:22715) nocodazole (CHEBI:34892) is a carbamate ester (CHEBI:23003) nocodazole (CHEBI:34892) is a thiophenes (CHEBI:26961)

IUPAC Name

methyl [5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl]carbamate

Synonyms	Sources
(5-(2-thienylcarbonyl)-1H-benzimidazol-2-yl)-carbamic acid methyl ester	ChemIDplus
methyl (5-(2-thienylcarbonyl))-1H-benzimidazole-2-ylcarbamate	ChemIDplus
methyl N-(5-thenoyl-2-benzimidazolyl)carbamate	NIST Chemistry WebBook
N-(5-(2-thenoyl)-2-benzimidazolyl)carbamic acid methyl ester	ChemIDplus
N-(5-(2-thienoyl)-2-benzimidazolyl)carbamic acid methyl ester	NIST Chemistry WebBook
oncodazole	ChemIDplus
R 17934	ChemIDplus
R-17934	ChEBI
R17,934	ChemIDplus

Last Modified

24 February 2016