nifurtimox   Click here for help

GtoPdb Ligand ID: 12364

Synonyms: BAY 2502 | BAY A2502 | Bayer 2502 | Lampit®
Approved drug
nifurtimox is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: Nifurtimox is an antimicrobial nitrofuran drug. The compound has antibacterial activity [2], but is primarily used as an antiprotozoal drug in the treatment of Chagas disease (American trypanosomiasis) and sleeping sickness (African trypanosomiasis).

nifurtimox is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 114.4
Molecular weight 287.06
XLogP 1.17
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1CS(=O)(=O)CCN1/N=C/c1ccc(o1)[N+](=O)[O-]
Isomeric SMILES CC1CS(=O)(=O)CCN1/N=C/c1ccc(o1)[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/b11-6+
InChI Key ARFHIAQFJWUCFH-IZZDOVSWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Nifurtimox is included in the World Health Organization's Model List of Essential Medicines as a treatment for Chagas disease and in combination with eflornithine as a treatment for African trypanosomiasis (sleeping sickness). In 2020, Nifurtimox was granted accelerated approval by the US FDA for the treatment of Chagas disease in pediatric patients. The drug is also licensed for use in a number of Central and South American countries.
Nifurtimox may have the potential to be repurposed as an antineoplastic therapy and has completed Phase 2 clinical evaluation for the treatment of neuroblastoma and medulloblastoma (NCT00601003).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00601003 Study of Nifurtimox to Treat Refractory or Relapsed Neuroblastoma or Medulloblastoma Phase 2 Interventional Wake Forest University Health Sciences
NCT02625974 Prospective Study of a Pediatric Nifurtimox Formulation for Chagas' Disease Phase 3 Interventional Bayer 1
NCT00146627 Efficacy - Safety of Eflornithine-Nifurtimox Combination Versus Eflornithine to Treat Human African Trypanosomiasis Phase 3 Interventional Drugs for Neglected Diseases 3
External links Click here for help
For extended ADME data see the following:

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