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Merck
CN

N3415

Sigma-Aldrich

Nifurtimox

≥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
EC Number:
245-531-0
MDL number:
MFCD00869254
UNSPSC Code:
12352200
PubChem Substance ID:
329818609
NACRES:
NA.77

Key Documents

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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

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000418356
0000418358
0000333766
0000333766
0000418358

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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
Diego Benitez et al.
Parasitology, 139(4), 506-515 (2012-01-06)
Cell death mechanisms in Trypanosoma cruzi have not been disclosed in detail though different conventional techniques have been used in the classification of parasite-cell death type. Nuclear magnetic resonance (NMR) has successfully been used as a tool to evaluate the
Claudio J Salomon
Journal of pharmaceutical sciences, 101(3), 888-894 (2011-12-14)
Hundred years after the discovery of Chagas' disease, there is a lack of effective treatment to control this neglected disease caused by the parasite Trypanosoma cruzi. The transmission is primarily through vector-borne blood transfusion or during pregnancy, producing high mortality
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
P P Simarro et al.
Parasitology, 139(7), 842-846 (2012-02-09)
Despite the fact that eflornithine was considered as the safer drug to treat human African trypanosomiasis (HAT) and has been freely available since 2001, the difficulties in logistics and cost burden associated with this drug meant that the toxic melarsoprol
View All Related Papers

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