Nifurtimox

Nifurtimox

250px
Systematic (IUPAC) name
(RS)-3-methyl-N-[(1E)-(5-nitro-2-furyl)methylene]thiomorpholin-4-amine 1,1-dioxide
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	Undetermined
Legal status	℞ Prescription only Not available in U.S. or Canada
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	Low
Metabolism	Hepatic (CYP involved)
Biological half-life	2.95 ± 1.19 hours
Excretion	Renal, very low
Identifiers
CAS Number	23256-30-6 N
ATC code	P01CC01 (WHO) QP51AC01 (WHO)
PubChem	CID: 31772
ChemSpider	29464 Y
UNII	M84I3K7C2O Y
KEGG	D00833 Y
ChEMBL	CHEMBL290960 N
Chemical data
Formula	C10H13N3O5S
Molecular mass	287.293 g/mol
SMILES O=S2(=O)CC(N(N=Cc1oc([N+]([O-])=O)cc1)CC2)C
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 Y Key:ARFHIAQFJWUCFH-UHFFFAOYSA-N Y
Physical data
Melting point	180 to 182 °C (356 to 360 °F)
NY (what is this?)  (verify)

Nifurtimox is a 5-nitrofuran used to treat diseases caused by trypanosomes including Chagas disease and sleeping sickness. It is given by mouth and not by injection.

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.

Medical uses

Being a nitroaromatic compound, nifurtimox undergoes reduction and eventually creates oxygen radicals such as superoxide. These radicals are toxic to T. cruzi. Mammalian cells are protected by presence of catalase, glutathione, peroxidases, and superoxide dismutase.

Nifurtimox has been used to treat Chagas disease, when it is given for 30 to 60 days, but gastrointestinal and neurological side effects have meant that benznidazole is now preferred for that indication.

Nifurtimox has also been used to treat African trypanosomiasis (sleeping sickness), and is active in the second stage of the disease (central nervous system involvement). When nifurtimox is given on its own, about half of all patients will relapse, but the combination of melarsoprol with nifurtimox appears to be efficacious. Trials are awaited comparing melarsoprol/nifurtimox against melarsoprol alone for African sleeping sickness.

Combination therapy with eflornithine and nifurtimox is safer and easier than treatment with eflornithine alone, and appears to be equally or more effective. It has been recommended as first-line treatment for second-stage African trypanosomiasis.

Investigational

Nifurtimox is in a phase-II clinical trial for the treatment of pediatric neuroblastoma and medulloblastoma.

Side effects, contraindications, and interactions

Side effects occur following chronic administration, particularly in elderly people. Major toxicities include immediate hypersensitivity such as anaphylaxis and delayed hypersensitivity reaction involving icterus and dermatitis. Gastrointestinal (GI) problems may occur that are severe enough to cause weight loss. Central nervous system disturbances and peripheral neuropathy may also occur. Cell mediated immunity may also be suppressed.

Manufacturing and availability

Nifurtimox is sold as Lampit by Bayer. It was previously known as Bayer 2502.

Nifurtimox is only licensed for use in Argentina and Germany, where it is sold as 120-mg tablets.