Compound ID | 3293

Update compound information

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):
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Molecular weight: 436.34
Iso. 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 Key: ZXSGSFMORAILEY-HNNXBMFYSA-N
Can. 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-]
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/49836057
Guide to Pharmacology: TBA-354
Citations:
  • https://journals.asm.org/doi/10.1128/aac.03823-14
  • https://pubmed.ncbi.nlm.nih.gov/28859520/
  • https://pubs.acs.org/doi/10.1021/jm101288t

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