Telacebec HCl

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MedKoo CAT#: 465388

CAS#: Telacebec HCl

Description: Telacebec, also known as Q203, is a new antitubercular drug with extremely potent activity against Mycobacterium ulcerans. Q203 inhibited the growth of MDR and 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.

Chemical Structure

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Telacebec HCl
CAS# Telacebec HCl
Instruction

Theoretical Analysis

MedKoo Cat#: 465388
Name: Telacebec HCl
CAS#: Telacebec HCl
Chemical Formula: C29H28ClF3N4O2
Exact Mass: 556.19
Molecular Weight: 557.014
Elemental Analysis: C, 62.53; H, 5.07; Cl, 6.36; F, 10.23; N, 10.06; O, 5.74

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 1334719-95-7 (free base)   1566517-83-6 (ditosylate)   Telacebec HCl    

Synonym: Telacebec; Q203; Q 203; Q-203;

IUPAC/Chemical Name: 6-chloro-2-ethyl-N-(4-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)benzyl)imidazo[1,2-a]pyridine-3-carboxamide

InChi Key: OJICYBSWSZGRFB-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: ClC(C=C1)=CN2C1=NC(CC)=C2C(NCC3=CC=C(N4CCC(C5=CC=C(OC(F)(F)F)C=C5)CC4)C=C3)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 557.01 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Lee BS, Hards K, Engelhart CA, Hasenoehrl EJ, Kalia NP, Mackenzie JS, Sviriaeva E, Chong SMS, Manimekalai MSS, Koh VH, Chan J, Xu J, Alonso S, Miller MJ, Steyn AJC, Grüber G, Schnappinger D, Berney M, Cook GM, Moraski GC, Pethe K. Dual inhibition of the terminal oxidases eradicates antibiotic-tolerant Mycobacterium tuberculosis. EMBO Mol Med. 2021 Jan 11;13(1):e13207. doi: 10.15252/emmm.202013207. Epub 2020 Dec 7. PMID: 33283973; PMCID: PMC7799364.

2: Chauffour A, Robert J, Veziris N, Aubry A, Pethe K, Jarlier V. Telacebec (Q203)-containing intermittent oral regimens sterilized mice infected with Mycobacterium ulcerans after only 16 doses. PLoS Negl Trop Dis. 2020 Aug 31;14(8):e0007857. doi: 10.1371/journal.pntd.0007857. PMID: 32866170; PMCID: PMC7494103.

3: Thomas SS, Kalia NP, Ruf MT, Pluschke G, Pethe K. Toward a Single-Dose Cure for Buruli Ulcer. Antimicrob Agents Chemother. 2020 Aug 20;64(9):e00727-20. doi: 10.1128/AAC.00727-20. PMID: 32631818; PMCID: PMC7449209.

4: Van Der Werf TS, Barogui YT, Converse PJ, Phillips RO, Stienstra Y. Pharmacologic management of Mycobacterium ulcerans infection. Expert Rev Clin Pharmacol. 2020 Apr;13(4):391-401. doi: 10.1080/17512433.2020.1752663. Epub 2020 Apr 20. PMID: 32310683.

5: de Jager VR, Dawson R, van Niekerk C, Hutchings J, Kim J, Vanker N, van der Merwe L, Choi J, Nam K, Diacon AH. Telacebec (Q203), a New Antituberculosis Agent. N Engl J Med. 2020 Mar 26;382(13):1280-1281. doi: 10.1056/NEJMc1913327. PMID: 32212527.

6: Almeida DV, Converse PJ, Omansen TF, Tyagi S, Tasneen R, Kim J, Nuermberger EL. Telacebec for Ultrashort Treatment of Buruli Ulcer in a Mouse Model. Antimicrob Agents Chemother. 2020 May 21;64(6):e00259-20. doi: 10.1128/AAC.00259-20. PMID: 32205344; PMCID: PMC7269501.

7: Chong SMS, Manimekalai MSS, Sarathy JP, Williams ZC, Harold LK, Cook GM, Dick T, Pethe K, Bates RW, Grüber G. Antituberculosis Activity of the Antimalaria Cytochrome bcc Oxidase Inhibitor SCR0911. ACS Infect Dis. 2020 Apr 10;6(4):725-737. doi: 10.1021/acsinfecdis.9b00408. Epub 2020 Mar 5. PMID: 32092260.

8: Lee BS, Sviriaeva E, Pethe K. Targeting the cytochrome oxidases for drug development in mycobacteria. Prog Biophys Mol Biol. 2020 May;152:45-54. doi: 10.1016/j.pbiomolbio.2020.02.001. Epub 2020 Feb 18. PMID: 32081616.

9: Poh W, Ab Rahman N, Ostrovski Y, Sznitman J, Pethe K, Loo SCJ. Active pulmonary targeting against tuberculosis (TB) via triple-encapsulation of Q203, bedaquiline and superparamagnetic iron oxides (SPIOs) in nanoparticle aggregates. Drug Deliv. 2019 Dec;26(1):1039-1048. doi: 10.1080/10717544.2019.1676841. PMID: 31691600; PMCID: PMC6844420.

10: Beites T, O'Brien K, Tiwari D, Engelhart CA, Walters S, Andrews J, Yang HJ, Sutphen ML, Weiner DM, Dayao EK, Zimmerman M, Prideaux B, Desai PV, Masquelin T, Via LE, Dartois V, Boshoff HI, Barry CE 3rd, Ehrt S, Schnappinger D. Plasticity of the Mycobacterium tuberculosis respiratory chain and its impact on tuberculosis drug development. Nat Commun. 2019 Oct 31;10(1):4970. doi: 10.1038/s41467-019-12956-2. PMID: 31672993; PMCID: PMC6823465.

11: Sorayah R, Manimekalai MSS, Shin SJ, Koh WJ, Grüber G, Pethe K. Naturally- Occurring Polymorphisms in QcrB Are Responsible for Resistance to Telacebec in Mycobacterium abscessus. ACS Infect Dis. 2019 Dec 13;5(12):2055-2060. doi: 10.1021/acsinfecdis.9b00322. Epub 2019 Oct 14. PMID: 31599569.

12: Kalia NP, Shi Lee B, Ab Rahman NB, Moraski GC, Miller MJ, Pethe K. Carbon metabolism modulates the efficacy of drugs targeting the cytochrome bc1:aa3 in Mycobacterium tuberculosis. Sci Rep. 2019 Jun 13;9(1):8608. doi: 10.1038/s41598-019-44887-9. PMID: 31197236; PMCID: PMC6565617.

13: Converse PJ, Almeida DV, Tyagi S, Xu J, Nuermberger EL. Shortening Buruli Ulcer Treatment with Combination Therapy Targeting the Respiratory Chain and Exploiting Mycobacterium ulcerans Gene Decay. Antimicrob Agents Chemother. 2019 Jun 24;63(7):e00426-19. doi: 10.1128/AAC.00426-19. PMID: 31036687; PMCID: PMC6591589.

14: Jeong JA, Oh JI. Alanine dehydrogenases in mycobacteria. J Microbiol. 2019 Feb;57(2):81-92. doi: 10.1007/s12275-019-8543-7. Epub 2019 Jan 31. PMID: 30706339.

15: Zeng S, Soetaert K, Ravon F, Vandeput M, Bald D, Kauffmann JM, Mathys V, Wattiez R, Fontaine V. Isoniazid Bactericidal Activity Involves Electron Transport Chain Perturbation. Antimicrob Agents Chemother. 2019 Feb 26;63(3):e01841-18. doi: 10.1128/AAC.01841-18. PMID: 30642937; PMCID: PMC6395907.

16: Scherr N, Bieri R, Thomas SS, Chauffour A, Kalia NP, Schneide P, Ruf MT, Lamelas A, Manimekalai MSS, Grüber G, Ishii N, Suzuki K, Tanner M, Moraski GC, Miller MJ, Witschel M, Jarlier V, Pluschke G, Pethe K. Targeting the Mycobacterium ulcerans cytochrome bc1:aa3 for the treatment of Buruli ulcer. Nat Commun. 2018 Dec 18;9(1):5370. doi: 10.1038/s41467-018-07804-8. PMID: 30560872; PMCID: PMC6299076.

17: Lee BS, Kalia NP, Jin XEF, Hasenoehrl EJ, Berney M, Pethe K. Inhibitors of energy metabolism interfere with antibiotic-induced death in mycobacteria. J Biol Chem. 2019 Feb 8;294(6):1936-1943. doi: 10.1074/jbc.RA118.005732. Epub 2018 Dec 7. PMID: 30530783; PMCID: PMC6369303.

18: Jeong JA, Park SW, Yoon D, Kim S, Kang HY, Oh JI. Roles of Alanine Dehydrogenase and Induction of Its Gene in Mycobacterium smegmatis under Respiration-Inhibitory Conditions. J Bacteriol. 2018 Jun 25;200(14):e00152-18. doi: 10.1128/JB.00152-18. PMID: 29712875; PMCID: PMC6018359.

19: Lu P, Asseri AH, Kremer M, Maaskant J, Ummels R, Lill H, Bald D. The anti- mycobacterial activity of the cytochrome bcc inhibitor Q203 can be enhanced by small-molecule inhibition of cytochrome bd. Sci Rep. 2018 Feb 8;8(1):2625. doi: 10.1038/s41598-018-20989-8. PMID: 29422632; PMCID: PMC5805707.

20: Kang S, Kim YM, Jeon H, Park S, Seo MJ, Lee S, Park D, Nam J, Lee S, Nam K, Kim S, Kim J. Synthesis and structure-activity relationships of novel fused ring analogues of Q203 as antitubercular agents. Eur J Med Chem. 2017 Aug 18;136:420-427. doi: 10.1016/j.ejmech.2017.05.021. Epub 2017 May 10. PMID: 28527405.