telacebec   Click here for help

GtoPdb Ligand ID: 12953

Synonyms: MMV687696 | Q203
PDB Ligand
Compound class: Synthetic organic
Comment: Telacebec is a first-in-class imidazopyridine amide that inhibits the mycobacterial cytochrome bc1 complex [3]. It is being clinically evaluated as a treatment for tuberculosis (TB).
Telacebec was one of the compounds with activity against Mycobacterium tuberculosis included in the Medicines for Malaria Venture (MMV) Pathogen Box (see MMVOpen for futher details).
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 57.17
Molecular weight 557.01
XLogP 5.29
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC1=C(C(=O)NCC2=CC=C(C=C2)N3CCC(CC3)C4=CC=C(C=C4)OC(F)(F)F)N5C=C(C=CC5=N1)Cl
Isomeric SMILES CCC1=C(N2C=C(C=CC2=N1)Cl)C(=O)NCC3=CC=C(C=C3)N4CCC(CC4)C5=CC=C(C=C5)OC(F)(F)F
InChI InChI=1S/C29H28ClF3N4O2/c1-2-25-27(37-18-22(30)7-12-26(37)35-25)28(38)34-17-19-3-8-23(9-4-19)36-15-13-21(14-16-36)20-5-10-24(11-6-20)39-29(31,32)33/h3-12,18,21H,2,13-17H2,1H3,(H,34,38)
InChI Key OJICYBSWSZGRFB-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
In December 2015, telacebec received Orphan Drug Designation (ODD) from the US FDA for the treatment of active TB. ODD was extended in January 2021 for the treatment of Buruli ulcer, an infectious disease caused by Mycobacterium ulcerans.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03563599 A Phase 2 Study to Evaluate Early Bactericidal Activity, Safety, Tolerability, and Pharmacokinetics of Multiple Oral Doses of Telacebec (Q203) Phase 2 Interventional Qurient Co., Ltd. 1