exeporfinium   Click here for help

GtoPdb Ligand ID: 13323

Synonyms: XF-73 (exeporfinium chloride)
Compound class: Synthetic organic
Comment: Exeporfinium is a novel dicationic porphyrin antibacterial compound with activity against a wide range of Gram-positive bacteria, including Staphylococcus aureus [2,4]. We show the structure of the parent molecule here. The INN represents the chloride salt form (XF-73, CAS number 718638-68-7) and this is also the form that is under clinical evaluation.
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 6
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 67.24
Molecular weight 694.91
XLogP 3.7
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
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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 C[N+](C)(C)CCCOC1=CC=C(C=C1)C2=C3C=CC(=N3)C=C4C=CC(=C(C5=CC=C(C=C5)OCCC[N+](C)(C)C)C6=NC(=CC7=CC=C2N7)C=C6)N4
Isomeric SMILES C[N+](C)(C)CCCOC1=CC=C(C=C1)C2=C3C=CC(=CC4=NC(=C(C5=CC=C(N5)C=C6C=CC2=N6)C7=CC=C(C=C7)OCCC[N+](C)(C)C)C=C4)N3
InChI InChI=1S/C44H50N6O2/c1-49(2,3)25-7-27-51-37-17-9-31(10-18-37)43-39-21-13-33(45-39)29-35-15-23-41(47-35)44(42-24-16-36(48-42)30-34-14-22-40(43)46-34)32-11-19-38(20-12-32)52-28-8-26-50(4,5)6/h9-24,29-30,45,48H,7-8,25-28H2,1-6H3/q+2
InChI Key KZTXNPVFWHWJSH-UHFFFAOYSA-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
Exeporfinium chloride is being developed by Destiny Pharma (UK) as a gel for nasal S. aureus decolonization prior to surgery, with the aim of preventing postoperative staphylococcal infections. Positive results from a Phase 2 study have been published [3] and it has been granted Qualified Infectious Disease Product (QIDP) and Fast Track Designation by the US FDA.
Exeporfinium chloride is also in the preclinical stage as treatment of antibactial-resistant biofilm and bacterial aggregate associated infections and as a topical preparation for the treatment of skin infections (access Destiny Pharma's pipeline webpage here).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Exeporfinium chloride has a dual mechanism of action. It binds selectively to the outer bacterial membrane leading to membrane disruption [4]. A separate, photodynamic mechanism, acts via the generation of reactive oxygen species [2].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01592214 Study of the Safety and Local Tolerability of Intranasal Gel Formulations of XF-73 Phase 1 Interventional National Institute of Allergy and Infectious Diseases (NIAID)
NCT02282605 Study of the Nasal Decolonisation of Staphylococcus Aureus (SA) and the Safety and Tolerability of XF-73 Nasal Gel in Healthy Subjects Phase 1/Phase 2 Interventional Destiny Pharma Plc
NCT03915470 Effect of Exeporfinium Chloride (XF-73) Gel on Nasal S.Aureus in Patients at Risk of Post-op Staphylococcal Infection Phase 2 Interventional Destiny Pharma Plc 3