Finafloxacin

• CAT Number: I002608
• CAS Number: 209342-40-5
• Molecular Formula: C20H19FN4O4
• Molecular Weight: 398.39
• Purity: ≥95%
• Synonyms: Finafloxacin
• Target: Bacterial
• Solubility: DMSO: ≤ 6.4 mg/mL
• Storage: Store at -20C
• IUPAC Name: 7-[(4aS,7aS)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• InChI: InChI=1S/C20H19FN4O4/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28)/t15-,16-/m0/s1
• InChIKey: FYMHQCNFKNMJAV-HOTGVXAUSA-N
• SMILES: C1CC1N2C=C(C(=O)C3=CC(=C(C(=C32)C#N)N4C[C@H]5[C@H](C4)OCCN5)F)C(=O)O

Finafloxacin (Cat No.:I002608) is a novel fluoroquinolone antibiotic with enhanced activity in acidic environments, making it particularly effective against infections in acidic tissues such as urinary tract infections and bacterial skin and soft tissue infections. It exhibits broad-spectrum activity against both Gram-positive and Gram-negative bacteria, including drug-resistant strains. Finafloxacin’s unique property of maintaining its antimicrobial activity in acidic conditions allows for improved efficacy and penetration into infected tissues. It has shown promising results in clinical trials and offers a potential therapeutic option for the treatment of various bacterial infections.

Overview of Clinical Research

Originator: Bayer
Developer: Alcon; MerLion Pharmaceuticals
Class: Antibacterials; Eye disorder therapies; Fluoroquinolones; Small molecules
Mechanism of Action: DNA gyrase inhibitors; DNA topoisomerase IV inhibitors
Orphan Drug Status: No
New Molecular Entity: Yes

Reference

1:Demonstrating the protective efficacy of the novel fluoroquinolone finafloxacin against an inhalational exposure to Burkholderia pseudomallei. Barnes KB, Hamblin KA, Richards MI, Laws TR, Vente A, Atkins HS, Harding SV.Antimicrob Agents Chemother. 2017 Apr 24. pii: AAC.00082-17. doi: 10.1128/AAC.00082-17. [Epub ahead of print] PMID: 28438936 Free Article
2:Pharmacodynamics of Finafloxacin, Ciprofloxacin, and Levofloxacin in Serum and Urine against TEM- and SHV-Type Extended-Spectrum-β-Lactamase-Producing Enterobacteriaceae Isolates from Patients with Urinary Tract Infections. Dalhoff A, Schubert S, Vente A.Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: e02446-16. doi: 10.1128/AAC.02446-16. Print 2017 May. PMID: 28193648 Free PMC Article
3:Finafloxacin overcomes Burkholderia pseudomallei efflux-mediated fluoroquinolone resistance. Randall LB, Georgi E, Genzel GH, Schweizer HP.J Antimicrob Chemother. 2017 Apr 1;72(4):1258-1260. doi: 10.1093/jac/dkw529. No abstract available. PMID: 28039270
4:Chemical structure and pharmacokinetics of novel quinolone agents represented by avarofloxacin, delafloxacin, finafloxacin, zabofloxacin and nemonoxacin. Kocsis B, Domokos J, Szabo D.Ann Clin Microbiol Antimicrob. 2016 May 23;15(1):34. doi: 10.1186/s12941-016-0150-4. Review. PMID: 27215369 Free PMC Article
5:High Efficacy of Finafloxacin on Helicobacter pylori Isolates at pH 5.0 Compared with That of Other Fluoroquinolones. Lee JW, Kim N, Nam RH, Kim JM, Park JY, Lee SM, Kim JS, Lee DH, Jung HC.Antimicrob Agents Chemother. 2015 Dec;59(12):7629-36. doi: 10.1128/AAC.01467-15. Epub 2015 Sep 28. PMID: 26416863 Free PMC Article
6:Finafloxacin for the treatment of urinary tract infections. Bartoletti R, Cai T, Perletti G, M E Wagenlehner F, Bjerklund Johansen TE.Expert Opin Investig Drugs. 2015;24(7):957-63. doi: 10.1517/13543784.2015.1052401. Epub 2015 Jun 12. Review. PMID: 26068714
7:Finafloxacin: first global approval. McKeage K.Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. Review. PMID: 25808831
8:Activity of the investigational fluoroquinolone finafloxacin and seven other antimicrobial agents against 114 obligately anaerobic bacteria. Genzel GH, Stubbings W, Stîngu CS, Labischinski H, Schaumann R.Int J Antimicrob Agents. 2014 Nov;44(5):420-3. doi: 10.1016/j.ijantimicag.2014.07.006. Epub 2014 Aug 19. PMID: 25264128
9:Comparative in vitro activity of finafloxacin against staphylococci displaying normal and small colony variant phenotypes. Idelevich EA, Kriegeskorte A, Stubbings W, Kahl BC, Peters G, Becker K.J Antimicrob Chemother. 2011 Dec;66(12):2809-13. doi: 10.1093/jac/dkr393. Epub 2011 Sep 21. PMID: 21948963
10:In vitro spectrum of activity of finafloxacin, a novel, pH-activated fluoroquinolone, under standard and acidic conditions. Stubbings W, Leow P, Yong GC, Goh F, Körber-Irrgang B, Kresken M, Endermann R, Labischinski H.Antimicrob Agents Chemother. 2011 Sep;55(9):4394-7. doi: 10.1128/AAC.00833-10. Epub 2011 Jun 27. PMID: 21709094 Free PMC Article