fobrepodacin   Click here for help

GtoPdb Ligand ID: 13062

Synonyms: pVXc-486 | SPR720
Compound class: Synthetic organic
Comment: Fobrepodacin (SPR720) is an orally administered prodrug that is being developed for the treatment of non-tuberculous mycobacterial pulmonary disease (NTM-PD) [3]. The active metabolite, SPR719, is a novel aminobenzimidazole antibacterial compound that is a dual Inhibitor of bacterial DNA gyrase and DNA topoisomerase 4 [1] .
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 12
Hydrogen bond donors 5
Rotatable bonds 9
Topological polar surface area 176.04
Molecular weight 508.44
XLogP -0.84
No. Lipinski's rules broken 2

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 CCNC(=O)NC1=NC2=C([C@H]3CCCO3)C(=C(C=C2N1)C4=CN=C(C(C)(C)OP(=O)(O)O)N=C4)F
Isomeric SMILES CCNC(=O)NC1=NC2=C(N1)C=C(C(=C2[C@H]3CCCO3)F)C4=CN=C(N=C4)C(C)(C)OP(=O)(O)O
InChI InChI=1S/C21H26FN6O6P/c1-4-23-20(29)28-19-26-13-8-12(16(22)15(17(13)27-19)14-6-5-7-33-14)11-9-24-18(25-10-11)21(2,3)34-35(30,31)32/h8-10,14H,4-7H2,1-3H3,(H2,30,31,32)(H3,23,26,27,28,29)/t14-/m1/s1
InChI Key COTQDURISRILOR-CQSZACIVSA-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
The results from a Phase 1 study suggest that predicted therapeutic exposure of SPR719 can be achieved with once-daily oral administration of fobrepodacin (NCT03796910) [4]. In February 2021, the US FDA placed a hold on the fobrepodacin clinical trial programme because of an analysis of results from a non-human primate toxicology study. This hold was lifted in January 2022 and Spero Therapeutics have begun recruitement for a Phase 2 study (NCT05496374) to evaluate fobrepodacin in participants with NTM-PD caused by Mycobacterium avium Complex (MAC).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05496374 A Study to Evaluate the Efficacy, Safety, Tolerability, and Pharmacokinetics of SPR720 as Compared With Placebo for the Treatment of Participants With Mycobacterium Avium Complex (MAC) Pulmonary Disease Phase 2 Interventional Spero Therapeutics
NCT04553406 Safety, Tolerability, Pharmacokinetics and Efficacy of SPR720 for the Treatment of Patients With Mycobacterium Avium Complex (MAC) Pulmonary Disease Phase 2 Interventional Spero Therapeutics Study was terminated pending the resolution of a clinical hold with US FDA.
NCT03796910 A Study of the Safety, Tolerability, and Pharmacokinetics of SPR720 in Healthy Volunteers Phase 1 Interventional Spero Therapeutics 4