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).
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 CDK toolkit. 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
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.

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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
References
1. Altcheh J, Castro L, Dib JC, Grossmann U, Huang E, Moscatelli G, Pinto Rocha JJ, Ramírez TE, CHICO Study Group. (2021)
Prospective, historically controlled study to evaluate the efficacy and safety of a new paediatric formulation of nifurtimox in children aged 0 to 17 years with Chagas disease one year after treatment (CHICO).
PLoS Negl Trop Dis, 15 (1): e0008912. [PMID:33412557]
2. Hof H. (1989)
Antibacterial activities of the antiparasitic drugs nifurtimox and benznidazole.
Antimicrob Agents Chemother, 33 (3): 404-5. [PMID:2729935]
3. Priotto G, Kasparian S, Mutombo W, Ngouama D, Ghorashian S, Arnold U, Ghabri S, Baudin E, Buard V, Kazadi-Kyanza S et al.. (2009)
Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial.
Lancet, 374 (9683): 56-64. [PMID:19559476]