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MedKoo Cat#: 555932 | Name: Telacebec free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Telacebec, also known as Q-203, is an antituberculosis agent and a potent inhibitor of mycobacterium tuberculosis protein potentially for the treatment of tuberculosis. Telacebec targets Mycobacterium tuberculosis cellular energy production through inhibition of the mycobacterial cytochrome bc1 complex. 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.

Chemical Structure

Telacebec free base
Telacebec free base
CAS#1334719-95-7 (free base)

Theoretical Analysis

MedKoo Cat#: 555932

Name: Telacebec free base

CAS#: 1334719-95-7 (free base)

Chemical Formula: C29H28ClF3N4O2

Exact Mass: 556.1853

Molecular Weight: 557.01

Elemental Analysis: C, 62.53; H, 5.07; Cl, 6.36; F, 10.23; N, 10.06; O, 5.74

Price and Availability

Size Price Availability Quantity
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
200mg USD 1,950.00 2 Weeks
500mg USD 2,950.00 2 Weeks
1g USD 3,850.00 2 Weeks
2g USD 6,450.00 2 Weeks
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Related CAS #
1334719-95-7 (free base) 1566517-83-6 (ditosylate) Telacebec HCl
Synonym
Telacebec free base; Q-203 free base; Q 203; Q203;
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
O=C(C1=C(CC)N=C2C=CC(Cl)=CN21)NCC3=CC=C(N4CCC(C5=CC=C(OC(F)(F)F)C=C5)CC4)C=C3
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Q-203 free base inhibits a mycobacterial respiratory chain, blocking oxidative phosphorylation.
In vitro activity:
Telacebec inhibits the mycobacterial respiratory supercomplex composed of complexes III and IV (CIII2CIV2). In mycobacterial electron transport chains, CIII2CIV2 replaces canonical CIII and CIV, transferring electrons from the intermediate carrier menaquinol to the final acceptor, molecular oxygen, while simultaneously transferring protons across the inner membrane to power ATP synthesis. This study suggest that telacebec prevents menaquinol oxidation by blocking two different menaquinol binding modes to prevent CIII2CIV2 activity. Reference: Elife. 2021 Sep 30;10:e71959. https://pubmed.ncbi.nlm.nih.gov/34590581/
In vivo activity:
Q203 exhibited high bactericidal activity compared to tedizolid, selamectin, and ivermectin and the benzothiazinone PBTZ169 were not active. Telacebec given twice a week in combination with a long-half-life compound, either rifapentine or bedaquiline, sterilized mouse footpads in 8 weeks, a total of 16 doses, and prevented relapse during a period of 20 weeks after the end of treatment. Reference: PLoS Negl Trop Dis. 2020 Aug 31;14(8):e0007857. https://pubmed.ncbi.nlm.nih.gov/32866170/
Solvent mg/mL mM
Solubility
DMF 14.0 25.13
DMSO 18.0 32.32
Ethanol 20.0 35.91
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:
1. Yanofsky DJ, Di Trani JM, Król S, Abdelaziz R, Bueler SA, Imming P, Brzezinski P, Rubinstein JL. Structure of mycobacterial CIII2CIV2 respiratory supercomplex bound to the tuberculosis drug candidate telacebec (Q203). Elife. 2021 Sep 30;10:e71959. doi: 10.7554/eLife.71959. PMID: 34590581; PMCID: PMC8523172. 2. Malík I, Čižmárik J, Kováč G, Pecháčová M, Hudecova L. Telacebec (Q203): Is there a novel effective and safe anti-tuberculosis drug on the horizon? Ceska Slov Farm. 2021 Winter;70(5):164-171. English. doi: 10.5817/CSF2021-5-164. PMID: 35114793. 3. 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. 4. Pethe K, Bifani P, Jang J, Kang S, Park S, Ahn S, Jiricek J, Jung J, Jeon HK, Cechetto J, Christophe T, Lee H, Kempf M, Jackson M, Lenaerts AJ, Pham H, Jones V, Seo MJ, Kim YM, Seo M, Seo JJ, Park D, Ko Y, Choi I, Kim R, Kim SY, Lim S, Yim SA, Nam J, Kang H, Kwon H, Oh CT, Cho Y, Jang Y, Kim J, Chua A, Tan BH, Nanjundappa MB, Rao SP, Barnes WS, Wintjens R, Walker JR, Alonso S, Lee S, Kim J, Oh S, Oh T, Nehrbass U, Han SJ, No Z, Lee J, Brodin P, Cho SN, Nam K, Kim J. Discovery of Q203, a potent clinical candidate for the treatment of tuberculosis. Nat Med. 2013 Sep;19(9):1157-60. doi: 10.1038/nm.3262. Epub 2013 Aug 4. PMID: 23913123.
In vitro protocol:
1. Yanofsky DJ, Di Trani JM, Król S, Abdelaziz R, Bueler SA, Imming P, Brzezinski P, Rubinstein JL. Structure of mycobacterial CIII2CIV2 respiratory supercomplex bound to the tuberculosis drug candidate telacebec (Q203). Elife. 2021 Sep 30;10:e71959. doi: 10.7554/eLife.71959. PMID: 34590581; PMCID: PMC8523172. 2. Malík I, Čižmárik J, Kováč G, Pecháčová M, Hudecova L. Telacebec (Q203): Is there a novel effective and safe anti-tuberculosis drug on the horizon? Ceska Slov Farm. 2021 Winter;70(5):164-171. English. doi: 10.5817/CSF2021-5-164. PMID: 35114793.
In vivo protocol:
1. 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. 2. Pethe K, Bifani P, Jang J, Kang S, Park S, Ahn S, Jiricek J, Jung J, Jeon HK, Cechetto J, Christophe T, Lee H, Kempf M, Jackson M, Lenaerts AJ, Pham H, Jones V, Seo MJ, Kim YM, Seo M, Seo JJ, Park D, Ko Y, Choi I, Kim R, Kim SY, Lim S, Yim SA, Nam J, Kang H, Kwon H, Oh CT, Cho Y, Jang Y, Kim J, Chua A, Tan BH, Nanjundappa MB, Rao SP, Barnes WS, Wintjens R, Walker JR, Alonso S, Lee S, Kim J, Oh S, Oh T, Nehrbass U, Han SJ, No Z, Lee J, Brodin P, Cho SN, Nam K, Kim J. Discovery of Q203, a potent clinical candidate for the treatment of tuberculosis. Nat Med. 2013 Sep;19(9):1157-60. doi: 10.1038/nm.3262. Epub 2013 Aug 4. PMID: 23913123.
1: Hards K, Cheung CY, Waller N, Adolph C, Keighley L, Tee ZS, Harold LK, Menorca A, Bujaroski RS, Buckley BJ, Tyndall JDA, McNeil MB, Rhee KY, Opel- Reading HK, Krause K, Preiss L, Langer JD, Meier T, Hasenoehrl EJ, Berney M, Kelso MJ, Cook GM. An amiloride derivative is active against the F1Fo-ATP synthase and cytochrome bd oxidase of Mycobacterium tuberculosis. Commun Biol. 2022 Feb 24;5(1):166. doi: 10.1038/s42003-022-03110-8. PMID: 35210534. 2: Lahiri R, Adams LB, Thomas SS, Pethe K. Sensitivity of Mycobacterium leprae to Telacebec. Emerg Infect Dis. 2022 Mar;28(3):749-751. doi: 10.3201/eid2803.210394. PMID: 35202539; PMCID: PMC8888226. 3: Malík I, Čižmárik J, Kováč G, Pecháčová M, Hudecova L. Telacebec (Q203): Is there a novel effective and safe anti-tuberculosis drug on the horizon? Ceska Slov Farm. 2021 Winter;70(5):164-171. English. doi: 10.5817/CSF2021-5-164. PMID: 35114793. 4: Gardini G, Gregori N, Matteelli A, Castelli F. Mycobacterial skin infection. Curr Opin Infect Dis. 2022 Apr 1;35(2):79-87. doi: 10.1097/QCO.0000000000000820. PMID: 35067521; PMCID: PMC8900879. 5: Lee BS, Pethe K. Telacebec: an investigational antibacterial for the treatment of tuberculosis (TB). Expert Opin Investig Drugs. 2022 Feb;31(2):139-144. doi: 10.1080/13543784.2022.2030309. Epub 2022 Jan 26. PMID: 35034512. 6: Tembe N, Machaba KE, Ndagi U, Kumalo HM, Mhlongo NN. Ursolic acid as a potential inhibitor of Mycobacterium tuberculosis cytochrome bc1 oxidase-a molecular modelling perspective. J Mol Model. 2022 Jan 13;28(2):35. doi: 10.1007/s00894-021-04993-w. PMID: 35022913. 7: Malík I, Čižmárik J, Kováč G, Pecháčová M, Hudecova L. Telacebec (Q203): Is there a novel effective and safe anti-tuberculosis drug on the horizon? Ceska Slov Farm. 2021 Fall;70(5):164–171. English. doi: 10.5817/CSF2021-5-164. PMID: 34875838. 8: Zhou S, Wang W, Zhou X, Zhang Y, Lai Y, Tang Y, Xu J, Li D, Lin J, Yang X, Ran T, Chen H, Guddat LW, Wang Q, Gao Y, Rao Z, Gong H. Structure of Mycobacterium tuberculosis cytochrome bcc in complex with Q203 and TB47, two anti-TB drug candidates. Elife. 2021 Nov 25;10:e69418. doi: 10.7554/eLife.69418. PMID: 34819223; PMCID: PMC8616580. 9: Wani MA, Dhaked DK. Targeting the cytochrome bc1 complex for drug development in M. tuberculosis: review. Mol Divers. 2021 Nov 11. doi: 10.1007/s11030-021-10335-y. Epub ahead of print. PMID: 34762234. 10: Kim J, Choi J, Kang H, Ahn J, Hutchings J, van Niekerk C, Park D, Kim J, Jeon Y, Nam K, Shin S, Shin BS. Safety, Tolerability, and Pharmacokinetics of Telacebec (Q203), a New Antituberculosis Agent, in Healthy Subjects. Antimicrob Agents Chemother. 2022 Jan 18;66(1):e0143621. doi: 10.1128/AAC.01436-21. Epub 2021 Oct 25. PMID: 34694872; PMCID: PMC8765288. 11: Thomas SS, Pethe K. Determination of Bioenergetic Parameters in Mycobacterium ulcerans. Methods Mol Biol. 2022;2387:219-230. doi: 10.1007/978-1-0716-1779-3_21. PMID: 34643916. 12: Yanofsky DJ, Di Trani JM, Król S, Abdelaziz R, Bueler SA, Imming P, Brzezinski P, Rubinstein JL. Structure of mycobacterial CIII2CIV2 respiratory supercomplex bound to the tuberculosis drug candidate telacebec (Q203). Elife. 2021 Sep 30;10:e71959. doi: 10.7554/eLife.71959. PMID: 34590581; PMCID: PMC8523172. 13: Sorayah R, Moraski GC, Barkan D, Pethe K. The QcrB Inhibitors TB47 and Telacebec Do Not Potentiate the Activity of Clofazimine in Mycobacterium abscessus. Antimicrob Agents Chemother. 2021 Nov 17;65(12):e0096421. doi: 10.1128/AAC.00964-21. Epub 2021 Sep 20. PMID: 34543090; PMCID: PMC8597762. 14: Gupta S, Fatima Z, Kumawat S. Study of the bioenergetics to identify the novel pathways as a drug target against Mycobacterium tuberculosis using Petri net. Biosystems. 2021 Nov;209:104509. doi: 10.1016/j.biosystems.2021.104509. Epub 2021 Aug 27. PMID: 34461147. 15: Komm O, Almeida DV, Converse PJ, Omansen TF, Nuermberger EL. Impact of Dose, Duration, and Immune Status on Efficacy of Ultrashort Telacebec Regimens in Mouse Models of Buruli Ulcer. Antimicrob Agents Chemother. 2021 Oct 18;65(11):e0141821. doi: 10.1128/AAC.01418-21. Epub 2021 Aug 30. PMID: 34460302; PMCID: PMC8522762. 16: Cai Y, Jaecklein E, Mackenzie JS, Papavinasasundaram K, Olive AJ, Chen X, Steyn AJC, Sassetti CM. Host immunity increases Mycobacterium tuberculosis reliance on cytochrome bd oxidase. PLoS Pathog. 2021 Jul 28;17(7):e1008911. doi: 10.1371/journal.ppat.1008911. PMID: 34320028; PMCID: PMC8351954. 17: Hopfner SM, Lee BS, Kalia NP, Miller MJ, Pethe K, Moraski GC. Structure guided generation of thieno[3,2-d]pyrimidin-4-amine Mycobacterium tuberculosis bd oxidase inhibitors. RSC Med Chem. 2021 Jan 12;12(1):73-77. doi: 10.1039/d0md00398k. PMID: 34046599; PMCID: PMC8130631. 18: Wang J, Jing W, Shi J, Huo F, Shang Y, Wang F, Chu N, Pang Y. Bipolar Distribution of Minimum Inhibitory Concentration of Q203 Across Mycobacterial Species. Microb Drug Resist. 2021 Aug;27(8):1013-1017. doi: 10.1089/mdr.2020.0239. Epub 2021 Feb 26. PMID: 33646044. 19: Hasenoehrl EJ, Wiggins TJ, Berney M. Bioenergetic Inhibitors: Antibiotic Efficacy and Mechanisms of Action in Mycobacterium tuberculosis. Front Cell Infect Microbiol. 2021 Jan 11;10:611683. doi: 10.3389/fcimb.2020.611683. PMID: 33505923; PMCID: PMC7831573. 20: Urban M, Šlachtová V, Brulíková L. Small organic molecules targeting the energy metabolism of Mycobacterium tuberculosis. Eur J Med Chem. 2021 Feb 15;212:113139. doi: 10.1016/j.ejmech.2020.113139. Epub 2020 Dec 29. PMID: 33422979.