TBI-166   Click here for help

GtoPdb Ligand ID: 12961

Synonyms: pyrifazimine
Compound class: Synthetic organic
Comment: TBI-166 is a riminophenazine class antimycobacterial compound and an analogue of clofazimine [1]. TBI-166 has advanced to clinical evaluation for the treatment of tuberculosis.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 80.04
Molecular weight 589.61
XLogP 4.83
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC1CCC(CC1)N=C2C=C3C(=NC4=C(C=CC=C4)N3C5=CC=C(C=C5)OC(F)(F)F)C=C2NC6=CC=CN=C6OC
Isomeric SMILES COC1CCC(CC1)N=C2C=C3C(=NC4=CC=CC=C4N3C5=CC=C(C=C5)OC(F)(F)F)C=C2NC6=C(N=CC=C6)OC
InChI InChI=1S/C32H30F3N5O3/c1-41-22-13-9-20(10-14-22)37-27-19-30-28(18-26(27)39-25-7-5-17-36-31(25)42-2)38-24-6-3-4-8-29(24)40(30)21-11-15-23(16-12-21)43-32(33,34)35/h3-8,11-12,15-20,22,39H,9-10,13-14H2,1-2H3
InChI Key GUSGYHIQYWRCQO-UHFFFAOYSA-N
References
1. Lu Y, Zheng M, Wang B, Fu L, Zhao W, Li P, Xu J, Zhu H, Jin H, Yin D et al.. (2011)
Clofazimine analogs with efficacy against experimental tuberculosis and reduced potential for accumulation.
Antimicrob Agents Chemother, 55 (11): 5185-93. [PMID:21844321]
2. Xu J, Wang B, Fu L, Zhu H, Guo S, Huang H, Yin D, Zhang Y, Lu Y. (2019)
In Vitro and In Vivo Activities of the Riminophenazine TBI-166 against Mycobacterium tuberculosis.
Antimicrob Agents Chemother, 63 (5). [PMID:30782992]