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N3415 Sigma-Aldrich

Nifurtimox

≥98% (HPLC)

Synonym: (±)-Nifurtimox, (RS)-3-methyl-N-[(1E)-(5-nitro-2-furyl)methylene]thiomorpholin-4-amine 1,1-dioxide, 3-Methyl-4-(5′-nitrofurylidene-amino)-tetrahydro-4H-1,4-thiazine-1,1-dioxide; 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine 1,1-dioxide, BAY 2502, Thiomorpholine, 3-methyl-4-((5-nitrofurfurylidene)amino)-,1,1-dioxide

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Properties

Related Categories Antioxidants and Cytoprotectants, Approved Therapeutics/Drug Candidates, Bayer, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   yellow to orange
solubility   DMSO: ≥13 mg/mL
originator   Bayer
storage temp.   room temp
SMILES string   CC1CS(=O)(=O)CCN1\N=C\c2ccc(o2)[N+]([O-])=O
InChI   1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+
InChI key   ARFHIAQFJWUCFH-IZZDOVSWSA-N

Description

General description

Nifurtimox acts as a hypoxia-activated cytotoxin, which specifically kills clonogenic tumor cells under hypoxic conditions. It is used to treat Chagas disease and African trypanosomiasis. Nifurtimox inhibits neuroblastoma and medulloblastoma cell growth.

Application

Nifurtimox has been used in drug treatment in culture media.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Nifurtimox is a nitrofurane derivative used to treat diseases caused by trypanosomes. Nifurtimox was discovered empirically and its mechanism of action is unclear. It is believed that nifurtimox exerts its biological activity through the bioreduction of the nitro-group to a nitro-anion radical which undergoes redox-cycling with molecular oxygen.

Features and Benefits

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Exposure to harsh conditions, cellular damage, and other factors can cause stress on cells. Stress attributed directly and indirectly to oxygen is referred to as oxidative stress, which is imposed on...
Keywords: Antimicrobials, Bioactive small molecules, Cancer, Diseases, Neurodegenerative Diseases, Oxidations

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