Nifurtimox

Nifurtimox
Clinical data

Trade names	Lampit
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	Undetermined
Routes of administration	By mouth
ATC code	P01CC01 (WHO) QP51AC01 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Low
Metabolism	Liver ( involved)
Biological half-life	2.95 ± 1.19 hours
Excretion	Kidney, very low
Identifiers
IUPAC name N-(3-Methyl-1,1-dioxido-4-thiomorpholinyl)-1-(5-nitro-2-furyl)methanimine
Synonyms	Bayer 2502
CAS Number	23256-30-6^N
PubChem (CID)	31772
ChemSpider	29464^Y
UNII	M84I3K7C2O^Y
KEGG	D00833^Y
ChEMBL	CHEMBL290960^N
ECHA InfoCard	100.041.377
Chemical and physical data
Formula	C₁₀H₁₃N₃O₅S
Molar mass	287.293 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Melting point	180 to 182 °C (356 to 360 °F)
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
^NY (what is this?)

Nifurtimox is a medication used to treat Chagas disease and sleeping sickness. For sleeping sickness it is used together with eflornithine. In Chagas disease it is a second line option to benznidazole. It is given by mouth.

Common side effects include abdominal pain, headache, nausea, and weight loss. There are concerns from animal studies that it may increase the risk of cancer but this concerns have not be found in human trials. Nifurtimox is not recommended in pregnancy or in those with significant kidney or liver problems. It is a type of nitrofuran.

Nifurtimox came into medication use in 1965. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is not available commercially in Canada or the United States. In the United States the medication can be gotten from the Center for Disease Control. It cost about 20 USD for a course of treatment as of 2013. In regions of the world where the disease is common nifurtimox is provided for free by the World Health Organization.

Nifurtimox has been used to treat Chagas disease, when it is given for 30 to 60 days. However, long term use of Nifurtimox does increase chances of adverse events like gastrointestinal and neurological side effects. Due to the low tolerance and completion rate of Nifurtimox, benznidazole is now being more considered for those who have Chagas disease and require long term treatment.

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.

...
Wikipedia