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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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.

✖
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine
International Nonproprietary Names Click here for help
INN number INN
2615 nifurtimox
Synonyms Click here for help
BAY 2502 | BAY A2502 | Bayer 2502 | Lampit®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nifurtimox
Other databases
CAS Registry No. 23256-30-6 (source: Scifinder)
ChEBI CHEBI:7566
ChEMBL Ligand CHEMBL290960
DrugBank Ligand DB11820
DrugCentral Ligand 1929
GtoPdb PubChem SID 479821155
PubChem CID 6842999
Search Google for chemical match using the InChIKey ARFHIAQFJWUCFH-IZZDOVSWSA-N
Search Google for chemicals with the same backbone ARFHIAQFJWUCFH
Search PubMed clinical trials nifurtimox
Search PubMed titles nifurtimox
Search PubMed titles/abstracts nifurtimox
UniChem Compound Search for chemical match using the InChIKey ARFHIAQFJWUCFH-IZZDOVSWSA-N
UniChem Connectivity Search for chemical match using the InChIKey ARFHIAQFJWUCFH-IZZDOVSWSA-N
Wikipedia Nifurtimox