Fluorothiazinone

Fluorothiazinone
Legal status
Legal status	Investigational;
Identifiers
	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 CID	132512026;
ChemSpider	88296074;
Chemical and physical data
Formula	C19H17F2N3O4S
Molar mass	421.42 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC1=C(C=CC(=C1)CN2C(=O)CSC(=N2)C(=O)NC3=C(C=C(C=C3)F)F)O;
	InChI InChI=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); Key: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]

References

^ Nesterenko LN, Zigangirova NA, Zayakin ES, Luyksaar SI, Kobets NV, Balunets DV, et al. (June 2016). "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. doi:10.1038/ja.2015.131. PMID 26732253.
^ Zigangirova NA, Kost EA, Didenko LV, Kapotina LN, Zayakin ES, Luyksaar SI, et al. (January 2016). "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. doi:10.1099/jmm.0.000189. PMID 26489840.
^ Provenzani A, Hospodar AR, Meyer AL, Leonardi Vinci D, Hwang EY, Butrus CM, et al. (August 2020). "Multidrug-resistant gram-negative organisms: a review of recently approved antibiotics and novel pipeline agents". International Journal of Clinical Pharmacy. 42 (4): 1016–1025. doi:10.1007/s11096-020-01089-y. PMID 32638294.
^ Zigangirova NA, Nesterenko LN, Sheremet AB, Soloveva AV, Luyksaar SI, Zayakin ES, et al. (April 2021). "Fluorothiazinon, a small-molecular inhibitor of T3SS, suppresses salmonella oral infection in mice". The Journal of Antibiotics. 74 (4): 244–254. doi:10.1038/s41429-020-00396-w. PMID 33479520.
^ Bondareva NE, Soloveva AV, Sheremet AB, Koroleva EA, Kapotina LN, Morgunova EY, et al. (March 2022). "Preventative treatment with Fluorothiazinon suppressed Acinetobacter baumannii-associated septicemia in mice". The Journal of Antibiotics. 75 (3): 155–163. doi:10.1038/s41429-022-00504-y. PMC 8777177. PMID 35064243.
^ Reig S, Le Gouellec A, Bleves S (2022). "What Is New in the Anti-Pseudomonas aeruginosa Clinical Development Pipeline Since the 2017 WHO Alert?". Frontiers in Cellular and Infection Microbiology. 12: 909731. doi:10.3389/fcimb.2022.909731. PMC 9308001. PMID 35880080.
^ Koroleva EA, Soloveva AV, Morgunova EY, Kapotina LN, Luyksaar SI, Luyksaar SV, et al. (May 2023). "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. doi:10.1038/s41429-023-00602-5. PMID 36922636.
^ Tsarenko SV, Zigangirova NA, Soloveva AV, Bondareva NE, Koroleva EA, Sheremet AB, et al. (July 2023). "A novel antivirulent compound fluorothiazinone inhibits Klebsiella pneumoniae biofilm in vitro and suppresses model pneumonia". The Journal of Antibiotics. 76 (7): 397–405. doi:10.1038/s41429-023-00621-2. PMID 37085670.
^ Strelnikova LN (2024). "От пенициллина — к фтортиазинону" [From penicillin to fluorothiazinone]. "Chemistry and Life" Popular science magazine (in Russian).
^ 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. doi:10.3390/antibiotics13060476 PMID 38927143

[1] Nesterenko LN, Zigangirova NA, Zayakin ES, Luyksaar SI, Kobets NV, Balunets DV, et al. (June 2016). "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. doi:10.1038/ja.2015.131. PMID 26732253.

[2] Zigangirova NA, Kost EA, Didenko LV, Kapotina LN, Zayakin ES, Luyksaar SI, et al. (January 2016). "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. doi:10.1099/jmm.0.000189. PMID 26489840.

[3] Provenzani A, Hospodar AR, Meyer AL, Leonardi Vinci D, Hwang EY, Butrus CM, et al. (August 2020). "Multidrug-resistant gram-negative organisms: a review of recently approved antibiotics and novel pipeline agents". International Journal of Clinical Pharmacy. 42 (4): 1016–1025. doi:10.1007/s11096-020-01089-y. PMID 32638294.

[4] Zigangirova NA, Nesterenko LN, Sheremet AB, Soloveva AV, Luyksaar SI, Zayakin ES, et al. (April 2021). "Fluorothiazinon, a small-molecular inhibitor of T3SS, suppresses salmonella oral infection in mice". The Journal of Antibiotics. 74 (4): 244–254. doi:10.1038/s41429-020-00396-w. PMID 33479520.

[5] Bondareva NE, Soloveva AV, Sheremet AB, Koroleva EA, Kapotina LN, Morgunova EY, et al. (March 2022). "Preventative treatment with Fluorothiazinon suppressed Acinetobacter baumannii-associated septicemia in mice". The Journal of Antibiotics. 75 (3): 155–163. doi:10.1038/s41429-022-00504-y. PMC 8777177. PMID 35064243.

[6] Reig S, Le Gouellec A, Bleves S (2022). "What Is New in the Anti-Pseudomonas aeruginosa Clinical Development Pipeline Since the 2017 WHO Alert?". Frontiers in Cellular and Infection Microbiology. 12: 909731. doi:10.3389/fcimb.2022.909731. PMC 9308001. PMID 35880080.

[7] Koroleva EA, Soloveva AV, Morgunova EY, Kapotina LN, Luyksaar SI, Luyksaar SV, et al. (May 2023). "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. doi:10.1038/s41429-023-00602-5. PMID 36922636.

[8] Tsarenko SV, Zigangirova NA, Soloveva AV, Bondareva NE, Koroleva EA, Sheremet AB, et al. (July 2023). "A novel antivirulent compound fluorothiazinone inhibits Klebsiella pneumoniae biofilm in vitro and suppresses model pneumonia". The Journal of Antibiotics. 76 (7): 397–405. doi:10.1038/s41429-023-00621-2. PMID 37085670.

[9] Strelnikova LN (2024). "От пенициллина — к фтортиазинону" [From penicillin to fluorothiazinone]. "Chemistry and Life" Popular science magazine (in Russian).

[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. doi:10.3390/antibiotics13060476 PMID 38927143

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See also

References