BTZ043
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MedKoo CAT#: 200584

CAS#: 1161233-85-7 (S-isomer)

Description: BTZ043 is a decaprenylphosphoryl-β-D-ribose 2'-epimerase (DprE1) inhibitor acting as a new antimycobacterial agent that kill Mycobacterium tuberculosis.


Chemical Structure

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BTZ043
CAS# 1161233-85-7 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 200584
Name: BTZ043
CAS#: 1161233-85-7 (S-isomer)
Chemical Formula: C17H16F3N3O5S
Exact Mass: 431.07628
Molecular Weight: 431.39
Elemental Analysis: C, 47.33; H, 3.74; F, 13.21; N, 9.74; O, 18.54; S, 7.43

Price and Availability

Size Price Availability Quantity
50.0mg USD 350.0 2 Weeks
100.0mg USD 650.0 2 Weeks
200.0mg USD 1050.0 2 Weeks
500.0mg USD 1850.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 4650.0 2 Weeks
5.0g USD 6950.0 2 Weeks
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Related CAS #: 957217-65-1 (racemic)   1161233-85-7 (S-isomer)    

Synonym: BTZ043; BTZ 043; BTZ-043.

IUPAC/Chemical Name: (S)-2-(2-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one

InChi Key: GTUIRORNXIOHQR-VIFPVBQESA-N

InChi Code: InChI=1S/C17H16F3N3O5S/c1-9-8-27-16(28-9)2-4-22(5-3-16)15-21-14(24)11-6-10(17(18,19)20)7-12(23(25)26)13(11)29-15/h6-7,9H,2-5,8H2,1H3/t9-/m0/s1

SMILES Code: O=C1N=C(N(CC2)CCC32OC[C@H](C)O3)SC4=C([N+]([O-])=O)C=C(C(F)(F)F)C=C14

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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 431.39 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

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1: Pasca MR, Degiacomi G, Ribeiro AL, Zara F, De Mori P, Heym B, Mirrione M, Brerra R, Pagani L, Pucillo L, Troupioti P, Makarov V, Cole ST, Riccardi G. Clinical isolates of Mycobacterium tuberculosis in four European hospitals are uniformly susceptible to benzothiazinones. Antimicrob Agents Chemother. 2010 Apr;54(4):1616-8. Epub 2010 Jan 19. PubMed PMID: 20086151; PubMed Central PMCID:  PMC2849388.

2: Makarov V, Manina G, Mikusova K, Möllmann U, Ryabova O, Saint-Joanis B, Dhar N, Pasca MR, Buroni S, Lucarelli AP, Milano A, De Rossi E, Belanova M, Bobovska A, Dianiskova P, Kordulakova J, Sala C, Fullam E, Schneider P, McKinney JD, Brodin P, Christophe T, Waddell S, Butcher P, Albrethsen J, Rosenkrands I, Brosch  R, Nandi V, Bharath S, Gaonkar S, Shandil RK, Balasubramanian V, Balganesh T, Tyagi S, Grosset J, Riccardi G, Cole ST. Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis. Science. 2009 May 8;324(5928):801-4. Epub 2009 Mar 19. PubMed PMID: 19299584.

BTZ043

50.0mg / USD 350.0


Additional Information

The new antitubercular drug candidate 2-[2-S-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one (BTZ043) targets the DprE1 (Rv3790) subunit of the enzyme decaprenylphosphoryl-beta-d-ribose 2'-epimerase. To monitor the potential development of benzothiazinone (BTZ) resistance, a total of 240 sensitive and multidrug-resistant Mycobacterium tuberculosis clinical isolates from four European hospitals were surveyed for the presence of mutations in the dprE1 gene and for BTZ susceptibility. All 240 strains were susceptible, thus establishing the baseline prior to the introduction of BTZ043 in clinical trials.
 
BTZ043 – proved particularly effective against the tubercle bacillus. The latterÂ’s cell walls, with their particular wax-rich structure, confer high resistance to antiseptics, some antibiotics and macrophages.
 
The new compound inhibits the enzyme which produces the molecule linking the various layers of the bacterial cell wall. Â“Without this enzyme, the bacterium explodes”, the Professor notes. Identifying this target was in itself the major discovery in this research as it paves the way for further therapeutic prospects. The research also relied on many advanced technologies developed by the EPFL. BTZ043 is now exiting preclinical research, soon to be the subject of clinical testing in humans. A new therapy could emerge in under 10 years.
Current developer:  the EPFL School of Life Sciences,