Fluorothiazinone Explained

Drug Name:Fluorothiazinone
Legal Status:Investigational
C:19
H:17
F:2
N:3
O:4
S:1
Iupac Name:N-(2,4-difluorophenyl)-4-[(3-ethoxy-4-hydroxyphenyl)methyl]-5-oxo-1,3,4-thiadiazine-2-carboxamide
Cas Number:1370706-59-4
Pubchem:132512026
Chemspiderid:88296074
Smiles:CCOC1=C(C=CC(=C1)CN2C(=O)CSC(=N2)C(=O)NC3=C(C=C(C=C3)F)F)O
Stdinchi:1S/C19H17F2N3O4S/c1-2-28-16-7-11(3-6-15(16)25)9-24-17(26)10-29-19(23-24)18(27)22-14-5-4-12(20)8-13(14)21/h3-8,25H,2,9-10H2,1H3,(H,22,27)
Stdinchikey:DAKWAZGLXWXDBB-UHFFFAOYSA-N

Fluorothiazinone (CL-55, Ftortiazinon, Фтортиазинон) is an antibiotic drug, first developed in Russia in 2010 and active against various species of Gram-negative bacteria through inhibition of the type III secretion system (T3SS). It has seen limited clinical use in Russia and is in clinical trials which may eventually see it accepted for use more widely.[1] [2] [3] [4] [5] [6] [7] [8] [9] [10]

See also

Notes and References

  1. Nesterenko LN, Zigangirova NA, Zayakin ES, Luyksaar SI, Kobets NV, Balunets DV, Shabalina LA, Bolshakova TN, Dobrynina OY, Gintsburg AL . A small-molecule compound belonging to a class of 2,4-disubstituted 1,3,4-thiadiazine-5-ones suppresses Salmonella infection in vivo . The Journal of Antibiotics . 69 . 6 . 422–427 . June 2016 . 10.1038/ja.2015.131 . 26732253 .
  2. Zigangirova NA, Kost EA, Didenko LV, Kapotina LN, Zayakin ES, Luyksaar SI, Morgunova EY, Fedina ED, Artyukhova OA, Samorodov AV, Kobets NV . A small-molecule compound belonging to a class of 2,4-disubstituted 1,3,4-thiadiazine-5-ones inhibits intracellular growth and persistence of Chlamydia trachomatis . Journal of Medical Microbiology . 65 . 1 . 91–98 . January 2016 . 10.1099/jmm.0.000189 . 26489840 .
  3. Provenzani A, Hospodar AR, Meyer AL, Leonardi Vinci D, Hwang EY, Butrus CM, Polidori P . Multidrug-resistant gram-negative organisms: a review of recently approved antibiotics and novel pipeline agents . International Journal of Clinical Pharmacy . 42 . 4 . 1016–1025 . August 2020 . 10.1007/s11096-020-01089-y . 32638294 .
  4. Zigangirova NA, Nesterenko LN, Sheremet AB, Soloveva AV, Luyksaar SI, Zayakin ES, Balunets DV, Gintsburg AL . Fluorothiazinon, a small-molecular inhibitor of T3SS, suppresses salmonella oral infection in mice . The Journal of Antibiotics . 74 . 4 . 244–254 . April 2021 . 10.1038/s41429-020-00396-w . 33479520 .
  5. Bondareva NE, Soloveva AV, Sheremet AB, Koroleva EA, Kapotina LN, Morgunova EY, Luyksaar SI, Zayakin ES, Zigangirova NA . Preventative treatment with Fluorothiazinon suppressed Acinetobacter baumannii-associated septicemia in mice . The Journal of Antibiotics . 75 . 3 . 155–163 . March 2022 . 10.1038/s41429-022-00504-y . 35064243 . 8777177 .
  6. Reig S, Le Gouellec A, Bleves S . What Is New in the Anti-Pseudomonas aeruginosa Clinical Development Pipeline Since the 2017 WHO Alert? . Frontiers in Cellular and Infection Microbiology . 2022 . 12 . 909731 . 10.3389/fcimb.2022.909731 . free . 35880080 . 9308001 .
  7. Koroleva EA, Soloveva AV, Morgunova EY, Kapotina LN, Luyksaar SI, Luyksaar SV, Bondareva NE, Nelubina SA, Lubenec NL, Zigangirova NA, Gintsburg AL . Fluorothiazinon inhibits the virulence factors of uropathogenic Escherichia coli involved in the development of urinary tract infection . The Journal of Antibiotics . 76 . 5 . 279–290 . May 2023 . 10.1038/s41429-023-00602-5 . 36922636 .
  8. Tsarenko SV, Zigangirova NA, Soloveva AV, Bondareva NE, Koroleva EA, Sheremet AB, Kapotina LN, Shevlyagina NV, Andreevskaya SG, Zhukhovitsky VG, Filimonova EV, Gintsburg AL . A novel antivirulent compound fluorothiazinone inhibits Klebsiella pneumoniae biofilm in vitro and suppresses model pneumonia . The Journal of Antibiotics . 76 . 7 . 397–405 . July 2023 . 10.1038/s41429-023-00621-2 . 37085670 .
  9. Web site: Strelnikova LN . От пенициллина — к фтортиазинону . From penicillin to fluorothiazinone . Russian . 2024 . "Chemistry and Life" Popular science magazine .
  10. Zigangirova NA, Lubenec NL, Beloborodov VB, Sheremet AB, Nelyubina SA, Bondareva NE, Zakharov KA, Luyksaar SI, Zolotov SA, Levchenko EU, Luyksaar SV, Koroleva EA, Fedina ED, Simakova YV, Pushkar DY, Gintzburg AL. A New "Non-Traditional" Antibacterial Drug Fluorothiazinone-Clinical Research in Patients with Complicated Urinary Tract Infections. Antibiotics (Basel). 2024 May 22;13(6):476.

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