Macozinone (MCZ; PBTZ169)

Class: Benzothiazinone

Details of activity:	Active against Mycobacterium tuberculosis; targets the DprE1 (decaprenylphosphoryl‐beta‐D‐ribose 2‐epimerase) involved in synthesis of mycobacteria cell wall components arabinogalactan and lipoarabinomannan (cell wall synthesis inhibitor)
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 developmental phase:	Phase 2 (NCT03334734)
Development status:	Inactive as of 2024
Reason Dropped:	Phase 2 clinical trial terminated due to slow enrollment

Chemical structure(s):
Canonical SMILES:	C1CCC(CC1)CN2CCN(CC2)C3=NC(=O)C4=CC(=CC(=C4S3)[N+](=O)[O-])C(F)(F)F
Isomeric SMILES:	C1CCC(CC1)CN2CCN(CC2)C3=NC(=O)C4=C(S3)C(=CC(=C4)C(F)(F)F)[N+](=O)[O-]
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
InChI Key:	BJDZBXGJNBMCAV-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/57331386

External links:
Main Source:	https://journals.asm.org/doi/10.1128/spectrum.02327-22