Compound ID | 2266

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Bithionol

Class: Membrane-active agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent. Interacts with and disrupts a bacterial mimetic lipid bilayer but not mammalian membranes
Target Pathogen: Active against Staphylococcus aureus including persister cells
Description: Synthetic compound (retinoid); a repurposed FDA-approved anthelminthic drug; >64 ug/ml haemolytic activity and membrane permeabilization against human erythrocytes and HKC-8 human renal proximal cells respectively (MIC at 0.5-2 ug/ml; shows efficacy in mouse MRSA infection model when in combination with gentamicin
Year first mentioned: 2019
Development status: Experimental
Chemical structure(s):
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Molecular weight: 356.05
Iso. SMILES: C1=C(C=C(C(=C1SC2=C(C(=CC(=C2)Cl)Cl)O)O)Cl)Cl
InChI Key: JFIOVJDNOJYLKP-UHFFFAOYSA-N
Can. SMILES: C1=C(C(=C(C=C1Cl)SC2=C(C(=CC(=C2)Cl)Cl)O)O)Cl
InChI: InChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/2406#section=Structures
Citations:
  • https://jpharmsci.org/article/S0022-3549(15)34919-4/pdf
  • https://www.pnas.org/doi/10.1073/pnas.1904700116

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