afabicin   Click here for help

GtoPdb Ligand ID: 10754

Synonyms: AFN-1720 | Debio 1450 | Debio1450
Compound class: Synthetic organic
Comment: Afabicin (DEBIO 1450) is an inhibitor of bacterial Fabl, the NADH-dependent enoyl reductase from the type II bacterial fatty acid biosynthesis pathway (FAS-II) [3]. This is a prodrug whose active metabolite is DEBIO 1452 (previously AFN-1252) [1].

afabicin is commercially available from our sponsors

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 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.

✖
Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 143.22
Molecular weight 485.14
XLogP 0.53
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
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.

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/)

✖
Canonical SMILES O=C(N(Cc1oc2c(c1C)cccc2)C)/C=C/c1cnc2c(c1)CCC(=O)N2COP(=O)(O)O
Isomeric SMILES O=C(N(Cc1oc2c(c1C)cccc2)C)/C=C/c1cnc2c(c1)CCC(=O)N2COP(=O)(O)O
InChI InChI=1S/C23H24N3O7P/c1-15-18-5-3-4-6-19(18)33-20(15)13-25(2)21(27)9-7-16-11-17-8-10-22(28)26(23(17)24-12-16)14-32-34(29,30)31/h3-7,9,11-12H,8,10,13-14H2,1-2H3,(H2,29,30,31)/b9-7+
InChI Key HFYMDQMXVPJNTH-VQHVLOKHSA-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
Afabicin has progressed to Phase 2 clinical evaluation for Staphylococcal bone or joint infections, or skin infections.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03723551 Study to Assess Safety, Tolerability and Efficacy of Afabicin in The Treatment of Participants With Bone or Joint Infection Due to Staphylococcus Phase 2 Interventional Debiopharm International SA
NCT02726438 Drug Penetration Into Bone After Repeated Oral Administration of Debio 1450 to Patients Undergoing Hip Replacement Surgery Phase 1 Interventional Debiopharm International SA This study confirmed drug penetration Into bone after repeated oral administration. 2
NCT02426918 Study of Debio 1450 for Bacterial Skin Infections Phase 2 Interventional Debiopharm International SA 4