6538. Nifurtimox

Nomenclature

CAS number: 23256-30-6
3-Methyl-N-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine 1,1-dioxide; 4-[(5-nitrofurfurylidene)amino]-3-methylthiomorpholine-1,1-dioxide; tetrahydro-3-methyl-4-[(5-nitrofurfurylidene)amino]-2H-1,4-thiazine 1,1-dioxide; 1-[(5-nitrofurfurylidene)amino]-2-methyltetrahydro-1,4-thiazine 4,4-dioxide; Bay 2502; Lampit (Bayer).
C10H13N3O5S; mol wt 287.29.
C 41.81%, H 4.56%, N 14.63%, O 27.85%, S 11.16%.

Description and references

Prepn from 5-nitrofurfural and 4-amino-3-methyltetrahydro-1,4-thiazine 1,1-dioxide: H. Herlinger et al., DE 1170957; eidem, US 3262930 (1964, 1966 both to Bayer). Series of articles on pharmacology and clinical findings: Arzneim.-Forsch. 22, 1563-1642 (1972). Toxicity data: K. Hoffmann, ibid. 1590. Spectrophotometric determn in pharmaceutical formulations: C. S. P. Sastry et al., Talanta 41, 1957 (1994) DOI PubMed. Clinical trial of combination with eflornithine in trypanosomiasis: G. Priotto et al., Clin. Infect. Dis. 45, 1435 (2007) DOI PubMed.

Chemical structure

Properties

Orange-red crystals from dil acetic acid, mp 180-182°. LD50 in mice, rats (mg/kg): 3720, 4050 by gavage (Hoffmann).

Therapeutic Category

Antiprotozoal (Trypanosoma).

Keywords

Antiprotozoal (Trypanosoma)