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N3415

Sigma-Aldrich

Nifurtimox

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C10H13N3O5S
Numéro CAS:
23256-30-6
Poids moléculaire :
287.29
Numéro CE :
245-531-0
Numéro MDL:
MFCD00869254
Code UNSPSC :
12352200
ID de substance PubChem :
329818609
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

yellow to orange

Solubilité

DMSO: ≥13 mg/mL

Auteur

Bayer

Température de stockage

room temp

Chaîne SMILES 

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+

Clé InChI

ARFHIAQFJWUCFH-IZZDOVSWSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Tolerance and safety of nifurtimox in patients with chronic chagas disease
Jackson Y, et al.
Clinical Infectious Diseases, 51(10), e69-e75 (2010)
Antitrypanosomal therapy for chronic Chagas' disease.
Caryn Bern
The New England journal of medicine, 364(26), 2527-2534 (2011-07-01)
Anis Rassi et al.
Infectious disease clinics of North America, 26(2), 275-291 (2012-05-29)
Chagas disease, also known as American trypanosomiasis, is a chronic infection caused by Trypanosoma cruzi, a protozoan parasite. It is transmitted to human beings mainly through the feces of infected triatomine bugs. The disease affects an estimated 8 to 10
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)
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