Nifurtimox

For research use only. Not for therapeutic Use.

  • CAT Number: R011691
  • CAS Number: 23256-30-6
  • Molecular Formula: C10H13N3O5S
  • Molecular Weight: 287.30
  • Purity: 98%
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Nifurtimox(Cat No.:R011691)is an antiparasitic medication used to treat Chagas disease, caused by Trypanosoma cruzi, and African trypanosomiasis (sleeping sickness). It works by producing reactive oxygen species within the parasite, leading to oxidative stress and damage to its DNA and cellular structures, ultimately causing parasite death. Nifurtimox is particularly effective in the acute phase of Chagas disease and is often used in combination with other treatments. Its ability to target the parasite’s metabolic processes makes it a vital tool in managing and controlling these neglected tropical diseases.


Catalog Number R011691
CAS Number 23256-30-6
Synonyms

3-Methyl-N-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine 1,1-Dioxide; 4-(5-Nitrofurfurylideneamino)-3-methylthiomorpholine 1,1-Dioxide; BAY 2502; Bayer 2502; Lampit; (+/-)-Nifurtimox;

Molecular Formula C10H13N3O5S
Purity 98%
Target Protein

P22513

Appearance Solid
Storage Dry, dark and at 2 - 8 °C for six months or -20°C for two years.
IC50 IC50s = 9.91, 12.28, and 10.44 μM against Taluahuén, LQ, and Brener strains of T
IUPAC Name (E)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine
InChI 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+
InChIKey ARFHIAQFJWUCFH-IZZDOVSWSA-N
SMILES CC1CS(=O)(=O)CCN1/N=C/C2=CC=C(O2)[N+](=O)[O-]
Reference

1:Safety Profile of Nifurtimox for Treatment of Chagas Disease in the United States. Forsyth CJ, Hernandez S, Olmedo W, Abuhamidah A, Traina MI, Sanchez DR, Soverow J, Meymandi SK.Clin Infect Dis. 2016 Oct 15;63(8):1056-1062. doi: 10.1093/cid/ciw477. Epub 2016 Jul 17. PMID: 27432838 Free PMC Article<br />
2:Nifurtimox Is Effective Against Neural Tumor Cells and Is Synergistic with Buthionine Sulfoximine. Du M, Zhang L, Scorsone KA, Woodfield SE, Zage PE.Sci Rep. 2016 Jun 10;6:27458. doi: 10.1038/srep27458. PMID: 27282514 Free PMC Article<br />
3:Pentacyclic nitrofurans that rapidly kill nifurtimox-resistant trypanosomes. Bruhn DF, Wyllie S, Rodríguez-Cortés A, Carrillo AK, Rakesh, Guy RK, Fairlamb AH, Lee RE.J Antimicrob Chemother. 2016 Apr;71(4):956-63. doi: 10.1093/jac/dkv417. Epub 2015 Dec 18. PMID: 26682963 Free PMC Article<br />
4:Determination of nifurtimox in dog plasma by stable-isotope dilution LC-MS/MS. Gnoth MJ, Hopfe PM, Thuss U.Bioanalysis. 2015 Nov;7(21):2777-87. doi: 10.4155/bio.15.185. Epub 2015 Nov 13. PMID: 26564573 <br />
5:Safety Profile of Nifurtimox and Treatment Interruption for Chronic Chagas Disease in Colombian Adults. Olivera MJ, Cucunubá ZM, álvarez CA, Nicholls RS.Am J Trop Med Hyg. 2015 Dec;93(6):1224-30. doi: 10.4269/ajtmh.15-0256. Epub 2015 Sep 21. PMID: 26392162 Free PMC Article<br />
6:Nifurtimox reduces N-Myc expression and aerobic glycolysis in neuroblastoma. Cabanillas Stanchi KM, Bruchelt G, Handgretinger R, Holzer U.Cancer Biol Ther. 2015;16(9):1353-63. doi: 10.1080/15384047.2015.1070987. Epub 2015 Jul 15. PMID: 26177922 Free PMC Article<br />
7:Negativation of Trypanosoma cruzi PCR within Six Months after Treatment of a Child with Nifurtimox. Pull L, Touafek F, Paris L, Le Loup G, Brutus L, Siriez JY.PLoS Negl Trop Dis. 2015 May 7;9(5):e0003667. doi: 10.1371/journal.pntd.0003667. eCollection 2015 May. No abstract available. PMID: 25951170 Free PMC Article<br />
8:Enantiomers of nifurtimox do not exhibit stereoselective anti-Trypanosoma cruzi activity, toxicity, or pharmacokinetic properties. Moraes CB, White KL, Braillard S, Perez C, Goo J, Gaspar L, Shackleford DM, Cordeiro-da-Silva A, Thompson RC, Freitas-Junior L, Charman SA, Chatelain E.Antimicrob Agents Chemother. 2015;59(6):3645-7. doi: 10.1128/AAC.05139-14. Epub 2015 Apr 6. PMID: 25845874 Free PMC Article<br />
9:Follow-up of an asymptomatic Chagas disease population of children after treatment with nifurtimox (Lampit) in a sylvatic endemic transmission area of Colombia. Bianchi F, Cucunubá Z, Guhl F, González NL, Freilij H, Nicholls RS, Ramírez JD, Montilla M, Flórez AC, Rosas F, Saavedra V, Silva N.PLoS Negl Trop Dis. 2015 Feb 27;9(2):e0003465. doi: 10.1371/journal.pntd.0003465. eCollection 2015 Feb. PMID: 25723465 Free PMC Article<br />
10:Serum biomarkers predictive of cure in Chagas disease patients after nifurtimox treatment. Santamaria C, Chatelain E, Jackson Y, Miao Q, Ward BJ, Chappuis F, Ndao M.BMC Infect Dis. 2014 Jun 3;14:302. doi: 10.1186/1471-2334-14-302. PMID: 24894358 Free PMC Article

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