TBA-354

Synonym(s): TBA354  |  TBA 354

Class: Nitroimidazole

Details of activity:	Active against Mycobacterium tuberculosis; likely generates reactive nitrogen species
Description:	Synthetic compound; superior to delamanid in chronic murine TB
Institute where first reported:	Global Alliance for TB Drug Development
Year first mentioned:	2010
Highest developmental phase:	Phase 1 (NCT02606214)
Development status:	Inactive
Reason Dropped:	Clinical study terminated (clinical hold by FDA); shows mild reversible neurotoxicity

Chemical structure(s):
Canonical SMILES:	C1=C(C=NC(=C1)C2=CC=C(C=C2)OC(F)(F)F)CO[C@H]3CN4C=C(N=C4OC3)[N+](=O)[O-]
Isomeric SMILES:	C1[C@@H](COC2=NC(=CN21)[N+](=O)[O-])OCC3=CN=C(C=C3)C4=CC=C(C=C4)OC(F)(F)F
InChI:	InChI=1S/C19H15F3N4O5/c20-19(21,22)31-14-4-2-13(3-5-14)16-6-1-12(7-23-16)10-29-15-8-25-9-17(26(27)28)24-18(25)30-11-15/h1-7,9,15H,8,10-11H2/t15-/m0/s1
InChI Key:	ZXSGSFMORAILEY-HNNXBMFYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/49836057

External links:
Main Source:	https://pubs.acs.org/doi/10.1021/jm101288t
Citations:	https://journals.asm.org/doi/10.1128/aac.03823-14 https://pubmed.ncbi.nlm.nih.gov/28859520/