WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 317113
CAS#: 209342-40-5 (free base)
Description: Finafloxacin is a fluoroquinolone antimicrobial agent that exhibits optimum efficacy in slightly acidic environments. It is being developed by MerLion Pharmaceuticals to treat serious bacterial infections associated with an acidic environment, including urinary tract infections and Helicobacter pylori infections. An otic suspension of finafloxacin (Xtoro™), developed by Alcon (a division of Novartis), was approved in 2014 in the USA for the treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. Oral and/or intravenous formulations are in phase I and II evaluation in uncomplicated urinary tract infections (Germany and Singapore), complicated urinary tract infections and pyelonephritis (Germany and Poland) and H. pylori infection (Germany).
MedKoo Cat#: 317113
CAS#: 209342-40-5 (free base)
Chemical Formula: C20H19FN4O4
Exact Mass: 398.13903
Molecular Weight: 398.39
Elemental Analysis: C, 60.30; H, 4.81; F, 4.77; N, 14.06; O, 16.06
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Related CAS #: 209342-41-6 (HCl) 209342-40-5 (free base)
Synonym: Finafloxacin, brand name Xtoro.
IUPAC/Chemical Name: 8-Cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
InChi Key: FYMHQCNFKNMJAV-HOTGVXAUSA-N
InChi Code: 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
SMILES Code: O=C(C1=CN(C2CC2)C3=C(C=C(F)C(N4C[C@]5([H])OCCN[C@@]5([H])C4)=C3C#N)C1=O)O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
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
The following data is based on the product molecular weight 398.39 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.
|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|
1: Bartoletti R, Cai T, Perletti G, M E Wagenlehner F, Bjerklund Johansen TE. Finafloxacin for the treatment of urinary tract infections. Expert Opin Investig Drugs. 2015;24(7):957-63. doi: 10.1517/13543784.2015.1052401. Epub 2015 Jun 12. PubMed PMID: 26068714.
2: McKeage K. Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. PubMed PMID: 25808831.
3: Genzel GH, Stubbings W, Stîngu CS, Labischinski H, Schaumann R. Activity of the investigational fluoroquinolone finafloxacin and seven other antimicrobial agents against 114 obligately anaerobic bacteria. Int J Antimicrob Agents. 2014 Nov;44(5):420-3. doi: 10.1016/j.ijantimicag.2014.07.006. Epub 2014 Aug 19. PubMed PMID: 25264128.
4: Idelevich EA, Kriegeskorte A, Stubbings W, Kahl BC, Peters G, Becker K. Comparative in vitro activity of finafloxacin against staphylococci displaying normal and small colony variant phenotypes. J Antimicrob Chemother. 2011 Dec;66(12):2809-13. doi: 10.1093/jac/dkr393. Epub 2011 Sep 21. PubMed PMID: 21948963.
5: Stubbings W, Leow P, Yong GC, Goh F, Körber-Irrgang B, Kresken M, Endermann R, Labischinski H. In vitro spectrum of activity of finafloxacin, a novel, pH-activated fluoroquinolone, under standard and acidic conditions. Antimicrob Agents Chemother. 2011 Sep;55(9):4394-7. doi: 10.1128/AAC.00833-10. Epub 2011 Jun 27. PubMed PMID: 21709094; PubMed Central PMCID: PMC3165343.
6: Patel H, Andresen A, Vente A, Heilmann HD, Stubbings W, Seiberling M, Lopez-Lazaro L, Pokorny R, Labischinski H. Human pharmacokinetics and safety profile of finafloxacin, a new fluoroquinolone antibiotic, in healthy volunteers. Antimicrob Agents Chemother. 2011 Sep;55(9):4386-93. doi: 10.1128/AAC.00832-10. Epub 2011 Jun 27. PubMed PMID: 21709093; PubMed Central PMCID: PMC3165282.
7: Lemaire S, Van Bambeke F, Tulkens PM. Activity of finafloxacin, a novel fluoroquinolone with increased activity at acid pH, towards extracellular and intracellular Staphylococcus aureus, Listeria monocytogenes and Legionella pneumophila. Int J Antimicrob Agents. 2011 Jul;38(1):52-9. doi: 10.1016/j.ijantimicag.2011.03.002. Epub 2011 May 18. PubMed PMID: 21596526.
8: Wagenlehner FM, Wagenlehner CM, Blenk B, Blenk H, Schubert S, Dalhoff A, Naber KG. Urinary pharmacokinetics and bactericidal activity of finafloxacin (200 and 800 mg) in healthy volunteers receiving a single oral dose. Chemotherapy. 2011;57(2):97-107. doi: 10.1159/000321028. Epub 2011 Feb 28. PubMed PMID: 21358200.
9: Dalhoff A, Stubbings W, Schubert S. Comparative in vitro activities of the novel antibacterial finafloxacin against selected Gram-positive and Gram-negative bacteria tested in Mueller-Hinton broth and synthetic urine. Antimicrob Agents Chemother. 2011 Apr;55(4):1814-8. doi: 10.1128/AAC.00886-10. Epub 2011 Jan 18. PubMed PMID: 21245444; PubMed Central PMCID: PMC3067158.
10: Emrich NC, Heisig A, Stubbings W, Labischinski H, Heisig P. Antibacterial activity of finafloxacin under different pH conditions against isogenic strains of Escherichia coli expressing combinations of defined mechanisms of fluoroquinolone resistance. J Antimicrob Chemother. 2010 Dec;65(12):2530-3. doi: 10.1093/jac/dkq375. Epub 2010 Oct 12. PubMed PMID: 20940181.
11: Higgins PG, Stubbings W, Wisplinghoff H, Seifert H. Activity of the investigational fluoroquinolone finafloxacin against ciprofloxacin-sensitive and -resistant Acinetobacter baumannii isolates. Antimicrob Agents Chemother. 2010 Apr;54(4):1613-5. doi: 10.1128/AAC.01637-09. Epub 2010 Jan 25. PubMed PMID: 20100879; PubMed Central PMCID: PMC2849356.