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N3415

Sigma-Aldrich

Nifurtimox

≥98% (HPLC)

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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5 MG
$149.40
25 MG
$464.80

About This Item

Empirical Formula (Hill Notation):
C10H13N3O5S
CAS Number:
23256-30-6
Molecular Weight:
287.29
EC Number:
245-531-0
MDL number:
MFCD00869254
UNSPSC Code:
12352200
PubChem Substance ID:
329818609
NACRES:
NA.77

$149.40

List Price$166.00Save 10%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

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

General description

Nifurtimox acts as a hypoxia-activated cytotoxin, which specifically kills clonogenic tumor cells under hypoxic conditions.[1] It is used to treat Chagas disease and African trypanosomiasis.[2] Nifurtimox inhibits neuroblastoma and medulloblastoma cell growth.[3]

Application

Nifurtimox has been used in drug treatment in culture media.[1]

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000418356
0000418358
0000333766
0000333766
0000418358

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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)
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
Tolerance and safety of nifurtimox in patients with chronic chagas disease
Jackson Y, et al.
Clinical Infectious Diseases, 51(10), e69-e75 (2010)
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
Monika Hułas-Stasiak et al.
Apoptosis : an international journal on programmed cell death, 16(10), 967-975 (2011-07-09)
This study was designed to determine follicular atresia in the newborn and the prepubertal spiny mouse. We analyzed the processes of follicle loss using classical markers of apoptosis (TUNEL reaction, active caspase-3) and autophagy (Lamp1). Numerous small clear vacuoles and
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