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Finafloxacin
Also known as: 209342-40-5, Xtoro, Finafloxacin [inn], D26osn9q4r, Al-60371, Chebi:85176
Molecular Formula
C20H19FN4O4
Molecular Weight
398.4  g/mol
InChI Key
FYMHQCNFKNMJAV-HOTGVXAUSA-N
FDA UNII
D26OSN9Q4R

Finafloxacin is a fluoroquinolone antibiotic indicated in the treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. Finafloxacin is marketed by Novartis under the brand Xtoro, and was approved by the FDA in December 2014.
Finafloxacin is a Quinolone Antimicrobial.
1 2D Structure

Finafloxacin

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 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
2.1.3 InChI Key
FYMHQCNFKNMJAV-HOTGVXAUSA-N
2.1.4 Canonical SMILES
C1CC1N2C=C(C(=O)C3=CC(=C(C(=C32)C#N)N4CC5C(C4)OCCN5)F)C(=O)O
2.1.5 Isomeric SMILES
C1CC1N2C=C(C(=O)C3=CC(=C(C(=C32)C#N)N4C[C@H]5[C@H](C4)OCCN5)F)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
D26OSN9Q4R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-quinolinecarboxylic Acid, 8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2h)-yl)-1,4-dihydro-4-oxo-

2. Xtoro

2.3.2 Depositor-Supplied Synonyms

1. 209342-40-5

2. Xtoro

3. Finafloxacin [inn]

4. D26osn9q4r

5. Al-60371

6. Chebi:85176

7. Finafloxacin (inn)

8. 8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2h)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

9. Bay35-3377

10. (-)-8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2h)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

11. 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

12. Gastrochinolon

13. Gastroquinolone

14. 8-cyano-1-cyclopropyl-6-fluoro-7-[(4as,7as)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2h)-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

15. Xtoro (tn)

16. Finafloxacin [mi]

17. Unii-d26osn9q4r

18. Finafloxacin [who-dd]

19. Schembl1002869

20. Chembl1908370

21. Gtpl10809

22. Dtxsid10175096

23. Finafloxacin [orange Book]

24. Bcp23882

25. Zinc3985346

26. Al60371

27. Cs-5557

28. Db09047

29. Ncgc00510315-02

30. (-)-8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2h)-yl)-4-oxo-1

31. Ac-29291

32. Hy-13451

33. D10575

34. Q21011229

35. 3-quinolinecarboxylic Acid,8-cyano-1-cyclopropyl-6-fluoro-7-[(4as,7as)-hexahydropyrrolo[3,4-b]-1,4-oxazin-6(2h)-yl]-1,4-dihydro-4-oxo-

36. 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,hydrochloride

37. 8-cyano-1-cyclopropyl-6-fluoro-7-((1s,6s)-2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

38. 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

2.4 Create Date
2006-10-26
3 Chemical and Physical Properties
Molecular Weight 398.4 g/mol
Molecular Formula C20H19FN4O4
XLogP3-0.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass398.13903326 g/mol
Monoisotopic Mass398.13903326 g/mol
Topological Polar Surface Area106 Ų
Heavy Atom Count29
Formal Charge0
Complexity806
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Finafloxacin is indicated for the treatment of acute otitis externa (AOE) with or without an otowick, caused by susceptible strains of Pseudomonas aeruginosa and Staphylococcus aureus in patients age 1 year and older.


FDA Label


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)


Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
FINAFLOXACIN
5.2.2 FDA UNII
D26OSN9Q4R
5.2.3 Pharmacological Classes
Chemical Structure [CS] - Quinolones
5.3 Mechanism of Action

Finafloxacin is a fluoroquinolone antibiotic, which selectively inhibit bacterial type II topoisomerase enzymes, DNA gyrase and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair and recombination.


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