brilacidin   Click here for help

GtoPdb Ligand ID: 13807

Synonyms: MMV1634402 | PMX30063
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Brilacidin is a small molecule mimetic of defensin, an antimicrobial peptide (also referred to as a host defence peptide) [6]. Brilacidin has anti-inflammatory properties and exhibits broad-spectrum antimicrobial activity, including antibacterial [4,6], antimalarial [1], antifungal [5], and antiviral [2-3]. Brilacidin (MMV1634402) was one of the chemotypes included in the Medicines for Malaria Pandemic Response Box.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 20
Hydrogen bond donors 10
Rotatable bonds 26
Topological polar surface area 312.44
Molecular weight 936.91
XLogP -0.5
No. Lipinski's rules broken 4

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(CCN=C(N)N)CC(=O)NC1=CC(=CC(=C1O[C@@H]2CCNC2)NC(=O)C3=NC=NC(=C3)C(=O)NC4=C(C(=CC(=C4)C(F)(F)F)NC(=O)CCCCN=C(N)N)O[C@@H]5CCNC5)C(F)(F)F
Isomeric SMILES C1CNC[C@@H]1OC2=C(C=C(C=C2NC(=O)C3=CC(=NC=N3)C(=O)NC4=CC(=CC(=C4O[C@@H]5CCNC5)NC(=O)CCCCN=C(N)N)C(F)(F)F)C(F)(F)F)NC(=O)CCCCN=C(N)N
InChI InChI=1S/C40H50F6N14O6/c41-39(42,43)21-13-25(57-31(61)5-1-3-9-53-37(47)48)33(65-23-7-11-51-18-23)27(15-21)59-35(63)29-17-30(56-20-55-29)36(64)60-28-16-22(40(44,45)46)14-26(34(28)66-24-8-12-52-19-24)58-32(62)6-2-4-10-54-38(49)50/h13-17,20,23-24,51-52H,1-12,18-19H2,(H,57,61)(H,58,62)(H,59,63)(H,60,64)(H4,47,48,53)(H4,49,50,54)/t23-,24-/m1/s1
InChI Key QPDYBCZNGUJZDK-DNQXCXABSA-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
Brilacidin is being developed by Innovation Pharma to target multiple indications. Phase 2 trials for acute bacterial skin and skin structure infections (ABSSSI) (NCT02052388), oral mucositis in patients undergoing chemoradiation for treatment of head and neck cancer (NCT02324335), and patients hospitalised due to COVID-19 (NCT04784897) have all been completed.
The US FDA has granted Qualified Infectious Disease Product (QIDP) designation to brilacidin as a treatment for ABSSSI and Fast Track designation for the prevention of oral mucositis and for the treatment of COVID-19.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02052388 Efficacy and Safety Study of Brilacidin to Treat Serious Skin Infections Phase 2 Interventional Innovation Pharmaceuticals, Inc.
NCT02324335 Study of the Effects of Brilacidin Oral Rinse on Radiation-induced Oral Mucositis in Patients With Head and Neck Cancer Phase 2 Interventional Innovation Pharmaceuticals, Inc.
NCT04784897 A Study to Evaluate the Efficacy and Safety of Brilacidin in Hospitalized Participants With COVID-19 Phase 2 Interventional Innovation Pharmaceuticals, Inc.