TELACEBEC DITOSYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C29H28ClF3N4O2.2C7H8O3S
Molecular Weight	901.41
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.CC2=CC=C(C=C2)S(O)(=O)=O.CCC3=C(N4C=C(Cl)C=CC4=N3)C(=O)NCC5=CC=C(C=C5)N6CCC(CC6)C7=CC=C(OC(F)(F)F)C=C7

InChI

InChIKey=CCGFTOLSNJBYDV-UHFFFAOYSA-N

InChI=1S/C29H28ClF3N4O2.2C7H8O3S/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;2*1-6-2-4-7(5-3-6)11(8,9)10/h3-12,18,21H,2,13-17H2,1H3,(H,34,38);2*2-5H,1H3,(H,8,9,10)

HIDE SMILES / InChI

Molecular Formula	C7H8O3S
Molecular Weight	172.202
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23913123 | https://www.ncbi.nlm.nih.gov/pubmed/27151308

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

Targets

Primary Target	Pharmacology	Condition	Potency
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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23913123 \| https://www.ncbi.nlm.nih.gov/pubmed/27151308	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23913123 https://www.ncbi.nlm.nih.gov/pubmed/27151308	Curative		Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 inducer 781	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP1A2 1524 CYP2C19 1478	P-gp 1537 HLM 31

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no [IC50 >10 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no [IC50 >25 uM]
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	no
HLM 31	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/	unlikely

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/23913123/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Discovery of Q203, a potent clinical candidate for the treatment of tuberculosis.	2013 Sep	23913123
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	24870926
New agents for the treatment of drug-resistant Mycobacterium tuberculosis.	2016 Jul 1	27151308
Exploiting the synthetic lethality between terminal respiratory oxidases to kill Mycobacterium tuberculosis and clear host infection.	2017 Jul 11	28652330

Patents

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 08:04:38 UTC 2023` Edited by `admin` on `Sat Dec 16 08:04:38 UTC 2023`
Record UNII	QRS143W4AR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TELACEBEC DITOSYLATE

Common Name

English

IMIDAZO(1,2-A)PYRIDINE-3-CARBOXAMIDE, 6-CHLORO-2-ETHYL-N-((4-(4-(4-(TRIFLUOROMETHOXY)PHENYL)-1-PIPERIDINYL)PHENYL)METHYL)-, 4-METHYLBENZENESULFONATE (1:2)

Systematic Name

English

Q-203 DITOSYLATE

Code

English

Code System Code Type Description

CAS

1566517-83-6

Created by admin on Sat Dec 16 08:04:38 UTC 2023 , Edited by admin on Sat Dec 16 08:04:38 UTC 2023

PRIMARY

PUBCHEM

91617801

Created by admin on Sat Dec 16 08:04:38 UTC 2023 , Edited by admin on Sat Dec 16 08:04:38 UTC 2023

PRIMARY

FDA UNII

QRS143W4AR

Created by admin on Sat Dec 16 08:04:38 UTC 2023 , Edited by admin on Sat Dec 16 08:04:38 UTC 2023

PRIMARY

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ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/23913123 | https://www.ncbi.nlm.nih.gov/pubmed/27151308

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23913123 | https://www.ncbi.nlm.nih.gov/pubmed/27151308

C_max

T_1/2

Drug as perpetrator