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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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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

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. 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 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Michael P Barrett et al.
Future microbiology, 6(9), 1037-1047 (2011-10-01)
Human African trypanosomiasis or 'sleeping sickness' is a neglected tropical disease caused by the parasite Trypanosoma brucei. A decade of intense international cooperation has brought the incidence to fewer than 10,000 reported cases per annum with anti-trypanosomal drugs, particularly against
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