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N3415

Sigma-Aldrich

Nifurtimox

≥98% (HPLC)

Synonyma:

(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

Empirický vzorec (Hillův zápis):
C10H13N3O5S
Číslo CAS:
23256-30-6
Molekulová hmotnost:
287.29
EC Number:
245-531-0
MDL number:
MFCD00869254
UNSPSC Code:
12352200
PubChem Substance ID:
329818609
NACRES:
NA.77

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. 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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Osvědčení o analýze (COA)

Lot/Batch Number
0000418356
0000418358
0000333766
0000333766
0000418358

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Navštívit knihovnu dokumentů

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
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
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
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
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
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