Nifurtimox

Nifurtimox
Clinical data
Trade namesLampit[1]
Other namesBayer 2502[2]
AHFS/Drugs.comDrugs.com archive
Lampit
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow
MetabolismLiver (Cytochrome P450 oxidase (CYP) involved)
Elimination half-life2.95 ± 1.19 hours
ExcretionKidney, very low
Identifiers
IUPAC name
  • N-(3-Methyl-1,1-dioxido-4-thiomorpholinyl)-1-(5-nitro-2-furyl)methanimine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.377
Chemical and physical data
FormulaC10H13N3O5S
Molar mass287.29 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point180 to 182 °C (356 to 360 °F)
SMILES
  • CC1CS(=O)(=O)CCN1N=CC2=CC=C(O2)[N+](=O)[O-]
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?)  (verify)

Nifurtimox, sold under the brand name Lampit, is a medication used to treat Chagas disease and sleeping sickness.[2][4] For sleeping sickness it is used together with eflornithine in nifurtimox-eflornithine combination treatment.[4] In Chagas disease it is a second-line option to benznidazole.[5] It is given by mouth.[2]

Common side effects include abdominal pain, headache, nausea, and weight loss.[2] There are concerns from animal studies that it may increase the risk of cancer but these concerns have not been found in human trials.[5] Nifurtimox is not recommended in pregnancy or in those with significant kidney or liver problems.[5] It is a type of nitrofuran.[5]

Nifurtimox came into medication use in 1965.[5] It is on the World Health Organization's List of Essential Medicines.[4] It is not available commercially in Canada.[2] It was approved for medical use in the United States in August 2020.[3] In regions of the world where the disease is common nifurtimox is provided for free by the World Health Organization (WHO).[6]

  1. ^ a b Cite error: The named reference Lampit FDA label was invoked but never defined (see the help page).
  2. ^ a b c d e "Nifurtimox (Systemic)". Drugs.com. 1995. Archived from the original on 20 December 2016. Retrieved 3 December 2016.
  3. ^ a b "Lampit: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on October 20, 2020. Retrieved 6 August 2020.
  4. ^ a b c World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. ^ a b c d e Bern C, Montgomery SP, Herwaldt BL, Rassi A, Marin-Neto JA, Dantas RO, et al. (November 2007). "Evaluation and treatment of chagas disease in the United States: a systematic review". JAMA. 298 (18): 2171–2181. doi:10.1001/jama.298.18.2171. PMID 18000201.
  6. ^ "Trypanosomiasis, human African (sleeping sickness)". World Health Organization. February 2016. Archived from the original on 4 December 2016. Retrieved 7 December 2016.
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