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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
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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