pravibismane   Click here for help

GtoPdb Ligand ID: 13590

Synonyms: BisEDT | MBN-101
Compound class: Synthetic organic
Comment: Pravibismane is a member of a novel class of bismuth antibacterials with broad-spectrum activity against both Gram- positive and Gram-negative bacterial pathogens and strong antibiofilm properties [3-4].
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 0
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 151.8
Molecular weight 694.52
XLogP 3.68
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 C1CS[Bi](S1)SCCS[Bi]2SCCS2
Isomeric SMILES C1CS[Bi](S1)SCCS[Bi]2SCCS2
InChI InChI=1S/3C2H6S2.2Bi/c3*3-1-2-4;;/h3*3-4H,1-2H2;;/q;;;2*+3/p-6
InChI Key GUTNLKRPYCTIHX-UHFFFAOYSA-H

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
Pravibismane is being developed by Microbion for the treatment of a range of resistant and difficult to treat bacterial infections. The drug has been granted Qualified Infectious Disease Product (QIDP) designation and Fast Track designation by the US FDA for adjunctive treatment of moderate and severe diabetic foot ulcer infection (DFI) and treatment of post-surgical orthopedic implant infections. In January 2024, pravibismane received Orphan Drug Designation from the FDA for the treatment of non-tuberculous mycobacterial (NTM) infections, in addition to that already granted for pulmonary infections in patients with cystic fibrosis.
Results from a Phase 1b clinical trial (NCT02723539) showed that pravibismane is a safe and potentially effective topical treatment for the managment of moderate or severe DFIs [2]. It progressed to Phase 2 evaluation as a treatment for DFIs (NCT05174806) and orthopaedic infections (NCT02436876), with these trials now complete.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Pravibismane acts rapidly to stop bacterial cell growth via a mechanism that disrupts cellular bioenergetics [1].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05174806 Multi-center Study to Assess Safety, Tolerability and Efficacy of Topical Pravibismane in Moderate DFI Patients Phase 2 Interventional Microbion Corporation
NCT02436876 Study to Assess Safety and Clinical Activity of Local MBN-101 in Treatment of Infected Bone Sites Phase 2 Interventional Microbion Corporation
NCT02723539 A Trial to Assess Safety and Efficacy of Topical MBN-101 in Patients With Moderate/ Severe DFI Phase 1 Interventional Microbion Corporation 2