fudapirine   Click here for help

GtoPdb Ligand ID: 13002

Synonyms: sudapyridine | WX-081
Compound class: Synthetic organic
Comment: Fudapirine (sudapyridine and formerly WX-081) is the lead from a novel diarylpyridine series with antimycobacterial activity and an analogue of bedaquiline [1,3]. Fudapirine has advanced to clinical evaluation for the treatment of tuberculosis.
The chemical structure of sudapyridine is identical to that which was submitted to the WHO for the INN fudapirine (proposed INN list 132, Feb 2025).
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 1
Rotatable bonds 9
Topological polar surface area 45.06
Molecular weight 537.09
XLogP 4.33
No. Lipinski's rules broken 1

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 CN(C)CC[C@@](C1=CC=CC2=C1C=CC=C2)([C@H](C3=CC=CC=C3)C4=CC(=CN=C4OC)C5=CC=C(C=C5)Cl)O
Isomeric SMILES CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=CC(=C4)C5=CC=C(C=C5)Cl)OC)O
InChI InChI=1S/C34H33ClN2O2/c1-37(2)21-20-34(38,31-15-9-13-25-10-7-8-14-29(25)31)32(26-11-5-4-6-12-26)30-22-27(23-36-33(30)39-3)24-16-18-28(35)19-17-24/h4-19,22-23,32,38H,20-21H2,1-3H3/t32-,34-/m1/s1
InChI Key MMUCHWPQRGEHDV-ZFEZZJPFSA-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
Fudapirine has completed a Phase 2 clinical trial (NCT04608955) assessing efficacy in patients with drug-susceptible and drug-resistant tuberculosis and has progressed to Phase 3 evaluation [2].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04608955 Evaluation of Early Bactericidal Activity and Safety in Pulmonary Tuberculosis With WX-081 Phase 2 Interventional Shanghai Jiatan Pharmatech Co., Ltd
NCT05824871 Sudapyridine (WX-081) in RR/MDR/XDR-tuberculosis Patients Phase 3 Interventional Shanghai Jiatan Pharmatech Co., Ltd