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Details

Stereochemistry ACHIRAL
Molecular Formula C29H28ClF3N4O2
Molecular Weight 557.006
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TELACEBEC

SMILES

CCC1=C(N2C=C(Cl)C=CC2=N1)C(=O)NCC3=CC=C(C=C3)N4CCC(CC4)C5=CC=C(OC(F)(F)F)C=C5

InChI

InChIKey=OJICYBSWSZGRFB-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C29H28ClF3N4O2
Molecular Weight 557.006
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Q203 (6-chloro-2-ethyl-N-(4-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)benzyl)imidazo [1,2-a]pyridine-3-carboxamide) is an an imidazopyridine antitubercular compound. Q203 targets the cytochrome b subunit (QcrB) of the cytochrome bc1 complex. This complex is an essential component of the respiratory electron transport chain of ATP synthesis. Q203 inhibited the growth of multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tuberculosis clinical isolates in culture broth medium in the low nanomolar range and was efficacious in a mouse model of tuberculosis at a dose less than 1 mg per kg body weight, which highlights the potency of this compound. In addition, Q203 displays pharmacokinetic and safety profiles compatible with once-daily dosing. Q203 is a promising new clinical candidate for the treatment of tuberculosis.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Ubiquinol-cytochrome c reductase cytochrome b subunit
2
Target ID: P9WP37
Gene ID: 887400.0
Gene Symbol: qcrB
Target Organism: Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase I
428
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.92 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/32205344
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
Q-203 plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1490 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28527405
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
Q-203 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
23.91 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/32205344
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
Q-203 plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
44100 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28527405
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
Q-203 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28527405
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
Q-203 plasma
Mus musculus
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32212527
Page: p.2
unhealthy, ADULT
Health Status: unhealthy
Condition: pulmonary tuberculosis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32212527
Page: p.2
Sources:
https://pubmed.ncbi.nlm.nih.gov/32212527
Page: p.2
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

inducer
781
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1461

CYP1A2
1524

CYP2C19
1478
P-gp
1537

HLM
31
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [IC50 >10 uM]
CYP2C19
1553
 no [IC50 >10 uM]
CYP2C9
1819
 no [IC50 >10 uM]
CYP2D6
1891
 no [IC50 >10 uM]
CYP3A4
1925
 no [IC50 >10 uM]
P-gp
1650
 no [IC50 >25 uM]
CYP3A4
1925
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
HLM
31
 unlikely
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P009YGV
https://www.1pchem.com/search?query=1P009YGV
AstaTech
43183
http://astatechinc.com/CPSResult.php?CRNO=43183
BLD Pharm
BD00813051
http://www.bldpharm.com/search/Search.html?keyword=BD00813051
Chem Scene
CS-6412
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6412
ChemShuttle
186315
https://www.chemshuttle.com/catalogsearch/result/?q=186315
Enamine
EN300-218150
https://www.enaminestore.com/catalog/EN300-218150
Excenen
EX-A2561
http://www.excenen.com/searchresultlist.php?id=EX-A2561
KeyOrganics
AS-35270
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35270
MedChem Express
HY-101040
https://www.medchemexpress.com/search.html?q=HY-101040&ft=&fa=&fp=
MolPort
MolPort-038-949-455
https://www.molport.com/shop/molecule-link/MolPort-038-949-455
Molnova
M11336
https://www.molnova.com/en/serch-list.html?keywords=M11336
MuseChem
I008935
https://www.musechem.com/product/I008935.html
TargetMol
T5400
https://www.targetmol.com/search?keyword=T5400
eMolecules
54860188
https://orderbb.emolecules.com/search/#?query=54860188
eNovation Chemicals
D621824
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621824&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-7294912765
https://mcule.com/MCULE-7294912765/
PubMed

PubMed

TitleDatePubMed
Discovery of Q203, a potent clinical candidate for the treatment of tuberculosis.
2013 Sep
Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug-resistant anti-tuberculosis agent.
2014 Jun 26
New agents for the treatment of drug-resistant Mycobacterium tuberculosis.
2016 Jul 1
Efflux Attenuates the Antibacterial Activity of Q203 in Mycobacterium tuberculosis.
2017 Jul
Exploiting the synthetic lethality between terminal respiratory oxidases to kill Mycobacterium tuberculosis and clear host infection.
2017 Jul 11
Patents

Patents

20130065884
2
20140155387
2
8865734
2
9029389
2
WO2011113606A1
2
WO2012143796A2
2

Sample Use Guides

In Vivo Use Guide
The Phase I clinical trial (clinicaltrials.gov identifier: NCT02530710) enrolling healthy patients is a dose-escalation study starting at 100 mg dosing that will be adjusted based on PK analysis.
Route of Administration: Oral
In Vitro Use Guide
Q203 inhibited the growth of multidrug-resistant (MDR) and extensively drug-resistant (XDR) M. tuberculosis clinical isolates in culture broth medium in the low nanomolar range
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:30:01 GMT 2023
Edited
by admin
on Sat Dec 16 08:30:01 GMT 2023
Record UNII
55G92WGH3X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TELACEBEC
INN   USAN  
Official Name English
TELACEBEC [USAN]
Common Name English
telacebec [INN]
Common Name English
6-CHLORO-2-ETHYL-N-((4-(4-(4-(TRIFLUOROMETHOXY)PHENYL)-1-PIPERDINYL)PHENYL)METHYL)-IMIDAZO(1,2-A)PYRIDINE-3-CARBOXAMIDE
Systematic Name English
Q203
Code English
Telacebec [WHO-DD]
Common Name English
Q-203
Code English
IMIDAZO(1,2-A)PYRIDINE-3-CARBOXAMIDE, 6-CHLORO-2-ETHYL-N-((4-(4-(4-(TRIFLUOROMETHOXY)PHENYL)-1-PIPERIDINYL)PHENYL)METHYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
FDA ORPHAN DRUG 499015
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
FDA ORPHAN DRUG 793920
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
Code System Code Type Description
SMS_ID
300000034390
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
CAS
1334719-95-7
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
NCI_THESAURUS
C152543
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
PUBCHEM
68234908
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
FDA UNII
55G92WGH3X
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
USAN
FG-22
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
INN
10573
Created by admin on Sat Dec 16 08:30:02 GMT 2023 , Edited by admin on Sat Dec 16 08:30:02 GMT 2023
PRIMARY
Related Record Type Details
Structure of TELACEBEC DITOSYLATE
SALT/SOLVATE -> PARENT
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
MYCOBACTERIUM TUBERCULOSIS (STRAIN ATCC 25618 / H37RV) CYTOCHROME BC1 COMPLEX CYTOCHROME B SUBUNIT
TARGET -> INHIBITOR
IN-VITRO
Scientific Literature
Related Record Type Details
Structure of TELACEBEC
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