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N3415

Nifurtimox

Name: Nifurtimox
Brand: SIGMA

≥98% (HPLC), Nitrofurane derivative, powder

Synonym(s):

(RS)-3-methyl-N-[(1E)-(5-nitro-2-furyl)methylene]thiomorpholin-4-amine 1,1-dioxide, (±)-Nifurtimox, 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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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₃N₃O₅S

CAS Number:

23256-30-6

Molecular Weight:

287.29

NACRES:

NA.77

PubChem Substance ID:

329818609

UNSPSC Code:

12352200

EC Number:

245-531-0

MDL number:

MFCD00869254

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Nifurtimox, ≥98% (HPLC)

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

Related Categories

Bioactive Small Molecules

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.

Biochem/physiol Actions

Nifurtimox is a nitrofurane derivative used to treat diseases caused by trypanosomes.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Serological and parasitological response in chronic Chagas patients 3 years after nifurtimox treatment.

Yves Jackson et al.

BMC infectious diseases, 13, 85-85 (2013-02-15)

With declining vectorial transmission, Chagas disease predominantly affects adults nowadays. The efficacy of nifurtimox in the chronic phase in adult patients is poorly known, particularly in regions where there is no risk of reinfection. Recommendations for treatment outcome assessment rely

The anti-protozoan drug nifurtimox preferentially inhibits clonogenic tumor cells under hypoxic conditions

Li Q, et al.

American Journal of Cancer Research, 7(5), 1084-1084 (2017)

Antiparasitic prodrug nifurtimox: revisiting its activation mechanism.

Hugo Cerecetto et al.

Future microbiology, 6(8), 847-850 (2011-08-25)

EVALUATION OF: Hall BS, Bot C, Wilkinson SR. Nifurtimox activation by trypanosomal type I nitroreductases generates cytotoxic nitrile metabolites. J. Biol. Chem. 286, 13088-13095 (2011). The prodrug nifurtimox has been one of the pharmacologic alternatives to treat Chagas disease and

Acute Chagas disease in a returning traveler.

Yvonne L Carter et al.

The American journal of tropical medicine and hygiene, 87(6), 1038-1040 (2012-10-24)

Acute Chagas disease is rarely recognized, and the risk for acquiring the disease is undefined in travelers to Central America. We describe a case of acute Chagas disease in a traveler to Costa Rica and highlight the need for increased

High-throughput decoding of antitrypanosomal drug efficacy and resistance.

Sam Alsford et al.

Nature, 482(7384), 232-236 (2012-01-27)

The concept of disease-specific chemotherapy was developed a century ago. Dyes and arsenical compounds that displayed selectivity against trypanosomes were central to this work, and the drugs that emerged remain in use for treating human African trypanosomiasis (HAT). The importance

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Global Trade Item Number

SKU	GTIN
N3415-25MG	04061834116066
N3415-5MG	04061834116073

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