PBTZ-169

Cas：1377239-83-2

Product Information：

PBTZ169, also known as macozinone, is a new drug candidate that inhibits decaprenyl-phosphoribose-epimerase (DprE1), an essential enzyme involved in the cell wall biosynthesis of Corynebacterineae. The MIC values of PBTZ169 ranged from 0.03 μg/mL to 0.0037 μg/mL. The MIC50 and MIC90 values of PBTZ169 were 0.0075 and 0.030 μg/mL, respectively. The MIC for PBTZ169 for N. brasiliensis HUJEG-1 was 0.0037 μg/mL. The MICs of SXT, DA-7218, and BTZ043 for this strain were 9.5/0.5, 8, and 0.125 μg/mL, respectively.

Chemical Formula: C20H23F3N4O3S

Exact Mass: 456.1443

Molecular Weight: 456.4842

Elemental Analysis: C, 52.62; H, 5.08; F, 12.49; N, 12.27; O, 10.51; S, 7.02

Synonym:

PBTZ169

PBTZ-169

PBTZ 169

macozinone

Chemical Name:

2-(4-(cyclohexylmethyl)piperazin-1-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one

InChi Key:

BJDZBXGJNBMCAV-UHFFFAOYSA-N

InChi Code:

InChI=1S/C20H23F3N4O3S/c21-20(22,23)14-10-15-17(16(11-14)27(29)30)31-19(24-18(15)28)26-8-6-25(7-9-26)12-13-4-2-1-3-5-13/h10-11,13H,1-9,12H2

Smiles Code:

O=C1N=C(N2CCN(CC3CCCCC3)CC2)SC4=C([N+]([O-])=O)C=C(C(F)(F)F)C=C14

Technical Data：

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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

In Vitro：

Macozinone (PBTZ169) is highly potent against M. tuberculosis in vitro, ex vivo, and in vivo.

References：

1. González-Martínez NA, Lozano-Garza HG, Castro-Garza J, De Osio-Cortez A, Vargas-Villarreal J, Cavazos-Rocha N, Ocampo-Candiani J, Makarov V, Cole ST, Vera-Cabrera L. In Vivo Activity of the Benzothiazinones PBTZ169 and BTZ043 against Nocardia brasiliensis. PLoS Negl Trop Dis. 2015 Oct 16;9(10):e0004022. doi: 10.1371/journal.pntd.0004022. eCollection 2015 Oct. PubMed PMID: 26474057; PubMed Central PMCID: PMC4608729.

2. Lechartier B, Cole ST. Mode of Action of Clofazimine and Combination Therapy with Benzothiazinones against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2015 Aug;59(8):4457-63. doi: 10.1128/AAC.00395-15. Epub 2015 May 18. PubMed PMID: 25987624; PubMed Central PMCID: PMC4505229.

3. Makarov V, Neres J, Hartkoorn RC, Ryabova OB, Kazakova E, Šarkan M, Huszár S, Piton J, Kolly GS, Vocat A, Conroy TM, Mikušová K, Cole ST. The 8-Pyrrole-Benzothiazinones Are Noncovalent Inhibitors of DprE1 from Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2015 Aug;59(8):4446-52. doi: 10.1128/AAC.00778-15. Epub 2015 May 18. PubMed PMID: 25987616; PubMed Central PMCID: PMC4505264.

4. Peng CT, Gao C, Wang NY, You XY, Zhang LD, Zhu YX, Xv Y, Zuo WQ, Ran K, Deng HX, Lei Q, Xiao KJ, Yu LT. Synthesis and antitubercular evaluation of 4-carbonyl piperazine substituted 1,3-benzothiazin-4-one derivatives. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1373-6. doi: 10.1016/j.bmcl.2015.02.061. Epub 2015 Mar 2. PubMed PMID: 25754492.

5. Makarov V, Lechartier B, Zhang M, Neres J, van der Sar AM, Raadsen SA, Hartkoorn RC, Ryabova OB, Vocat A, Decosterd LA, Widmer N, Buclin T, Bitter W, Andries K, Pojer F, Dyson PJ, Cole ST. Towards a new combination therapy for tuberculosis with next generation benzothiazinones. EMBO Mol Med. 2014 Mar;6(3):372-83. doi: 10.1002/emmm.201303575. Epub 2014 Feb 5. PubMed PMID: 24500695; PubMed Central PMCID: PMC3958311.

Products are for research use only. Not for human use.