contezolid acefosamil (parent)   Click here for help

GtoPdb Ligand ID: 10796

Synonyms: MRX-4
Compound class: Synthetic organic
Comment: Contezolid acefosamil is delivered as the sodium salt, which is represented by PubChem CID 131750213 [2]. We show the structure for the parent molecule here. The active moiety contezolid acts as a potent oxazolidinone antibacterial against Gram-positive pathogens [1].
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 10
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 152.53
Molecular weight 530.08
XLogP 2
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
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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 O=C1CCN(C=C1)c1c(F)cc(c(c1F)F)N1C[C@@H](OC1=O)CN(P(=O)(OC(=O)C)O)c1ccon1
Isomeric SMILES O=C1CCN(C=C1)c1c(F)cc(c(c1F)F)N1C[C@@H](OC1=O)CN(P(=O)(OC(=O)C)O)c1ccon1
InChI InChI=1S/C20H18F3N4O8P/c1-11(28)35-36(31,32)27(16-4-7-33-24-16)10-13-9-26(20(30)34-13)15-8-14(21)19(18(23)17(15)22)25-5-2-12(29)3-6-25/h2,4-5,7-8,13H,3,6,9-10H2,1H3,(H,31,32)/t13-/m1/s1
InChI Key YCRAGJLWFBGKFE-CYBMUJFWSA-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
In September 2023, contezolid acefosamil was granted Qualified Infectious Disease Product (QIDP) and Fast Track Designation by the US FDA for the treatment of moderate to severe diabetic foot infections (DFI). It was previously granted QIDP and Fast Track Designation (in 2018) for the treatment of acute bacterial skin and skin structure infections (ABSSSI). Contezolid acefosamil is formulated for intravenous administration and has completed Phase 2 clinical evaluation for the treatment of ABSSSI (NCT03747497) and is currently being studied in a Phase 3 trial for the treatment of patients with DFI (NCT05369052).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03033329 Single Dose Escalation and Multiple Dose Escalation Trial of an Intravenous Formulation of MRX-4 Phase 1 Interventional MicuRx
NCT03747497 Contezolid Acefosamil Versus Linezolid for the Treatment of Acute Bacterial Skin and Skin Structure Infection Phase 2 Interventional MicuRx
NCT05369052 Safety and Efficacy Study of Contezolid Acefosamil and Contezolid Compared to Linezolid Administered Intravenously and Orally to Adults With Moderate or Severe Diabetic Foot Infections (DFI) Phase 3 Interventional MicuRx