Compound ID | 2891

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Macozinone (MCZ; PBTZ169)

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Antimycobacterial
Mechanism of action: Mycolic acid synthesis inhibitor. Targets the DprE1 (decaprenylphosphoryl‐beta‐D‐ribose 2‐epimerase) involved in synthesis of mycobacteria cell wall components arabinogalactan and lipoarabinomannan (cell wall synthesis inhibitor)
Target Pathogen: Active against Mycobacterium tuberculosis
Description: Synthetic compound of piperazine-containing benzothiazinone scaffold; a new extended-release formulation as initial immediate-release dispersible tablet formulation shows rapid elimination and low bioavailability in humans
Institute where first reported: NovaMedica Innotech (Moscow, Russia)
Year first mentioned: 2014
Highest development stage: Phase 2 (NCT03334734)
Development status: Inactive as of 2024
Reason dropped: Phase 2 clinical trial terminated due to slow enrollment
Chemical structure(s):
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Molecular weight: 456.48
Iso. SMILES: C1CCC(CC1)CN2CCN(CC2)C3=NC(=O)C4=C(S3)C(=CC(=C4)C(F)(F)F)[N+](=O)[O-]
InChI Key: BJDZBXGJNBMCAV-UHFFFAOYSA-N
Can. SMILES: C1CCC(CC1)CN2CCN(CC2)C3=NC(=O)C4=CC(=CC(=C4S3)[N+](=O)[O-])C(F)(F)F
InChI: InChI=1S/C20H23F3N4O3S/c21-20(22,23)14-10-15-17(16(11-14)27(29)30)31-19(24-18(15)28)26-8-6-25(7-9-26)12-13-4-2-1-3-5-13/h10-11,13H,1-9,12H2
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/57331386
Guide to Pharmacology: macozinone
Citation: https://journals.asm.org/doi/10.1128/spectrum.02327-22

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