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Chemistry

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Also known as: 189279-58-1, Abt-492, Baxdela, Wq-3034, Abt492, Abt 492

Molecular Formula

C₁₈H₁₂ClF₃N₄O₄

Molecular Weight

440.8 g/mol

InChI Key

DYDCPNMLZGFQTM-UHFFFAOYSA-N

FDA UNII

6315412YVF

Delafloxacin is a fluoroquinolone antibiotic which has been used in trials studying the treatment and basic science of Gonorrhea, Hepatic Impairment, Bacterial Skin Diseases, Skin Structure Infections, and Community Acquired Pneumonia, among others. It was approved in June 2017 under the trade name Baxdela for use in the treatment of acute bacterial skin and skin structure infections.

Delafloxacin is a Fluoroquinolone Antibacterial.

1 2D Structure

Delafloxacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid

2.1.2 InChI

InChI=1S/C18H12ClF3N4O4/c19-12-13-7(1-9(20)14(12)25-3-6(27)4-25)15(28)8(18(29)30)5-26(13)17-11(22)2-10(21)16(23)24-17/h1-2,5-6,27H,3-4H2,(H2,23,24)(H,29,30)

2.1.3 InChI Key

DYDCPNMLZGFQTM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C(CN1C2=C(C=C3C(=C2Cl)N(C=C(C3=O)C(=O)O)C4=C(C=C(C(=N4)N)F)F)F)O

2.2 Other Identifiers

2.2.1 UNII

6315412YVF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

2. 3-quinolinecarboxylic Acid, 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-

3. Abt 492

4. Abt-492

5. Abt492

6. Baxdela

7. Rx-3341

2.3.2 Depositor-Supplied Synonyms

1. 189279-58-1

2. Abt-492

3. Baxdela

4. Wq-3034

5. Abt492

6. Abt 492

7. 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

8. Rx-3341

9. 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic Acid

10. Delafloxacin [usan]

11. 3-quinolinecarboxylic Acid, 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-

12. 6315412yvf

13. Delafloxacin (usan)

14. 1-(6-amino-3,5-difluoro-2-pyridyl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-quinoline-3-carboxylic Acid

15. Delafloxacin [usan:inn]

16. Delafloxacinum

17. Quofenix

18. Unii-6315412yvf

19. Abbott 492

20. Delafloxacinabt-492

21. Delafloxacin [mi]

22. Delafloxacin [inn]

23. Delafloxacin [who-dd]

24. Schembl294694

25. Chembl2105637

26. Gtpl10799

27. Amy4217

28. Delafloxacin, >=98% (hplc)

29. Dtxsid40172331

30. Ex-a2331

31. Zinc3827556

32. Bdbm50560872

33. S1553

34. Cs-1478

35. Db11943

36. Sb16746

37. Wq 3034

38. Ncgc00390187-01

39. Ncgc00390187-02

40. Ac-30739

41. As-75147

42. Hy-14814

43. Delafloxacin 100 Microg/ml In Acetonitrile

44. Ft-0697895

45. C73623

46. D09330

47. Rx-3341; Wq-3034; Abt492; Delafloxacin

48. Abt-492(delafloxacin, Rx-3341, Wq-3034)

49. A-319492

50. Q5253067

51. 189279-58-1, 339591-82-1 (sodium Salt)

52. 1-(6-amino-3,5-difluoropyridine-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidine-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₂ClF₃N₄O₄
Molecular Weight	440.8 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	3
Exact Mass	440.0499171 g/mol
Monoisotopic Mass	440.0499171 g/mol
Topological Polar Surface Area	120 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	755
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	BAXDELA
Active Ingredient	DELAFLOXACIN MEGLUMINE
Company	MELINTA THERAPS INC (Application Number: N208610); MELINTA THERAPS INC (Application Number: N208611)

4.2 Drug Indication

Delafloxacin is indicated for the treatment of acute bacterial skin and skin structure infections caused by the Gram-positive organisms Staphylococcus aureus (including methicillin-resistant and methicillin-susceptible isolates), Staphylococcus haemolyticus, Staphylococcus lugdunensis, Streptococcus agalactiae, Streptococcus anginosus Group (including Streptococcus anginosus, Streptococcus intermedius, and Streptococcus constellatus), Streptococcus pyogenes, and Enterococcus faecalis as well as the Gram-negative organisms Escherichia coli, Enterobacter cloacae, Klebsiella pneumoniae, and Pseudomonas aeruginosa.

FDA Label

Quofenix is indicated for the treatment of the following infections in adults:

- acute bacterial skin and skin structure infections (ABSSSI),

- community-acquired pneumonia (CAP), when it is considered inappropriate to use other antibacterial agents that are commonly recommended for the initial treatment of these infections (see sections 4. 4 and 5. 1).

Consideration should be given to official guidance on the appropriate use of antibacterial agents.

Treatment of community-acquired pneumonia

Treatment of local infections of skin and subcutaneous tissues

5 Pharmacology and Biochemistry

5.1 Pharmacology

Delafloxacin is a fluoroquinolone antibacterial drug which kills bacterial cells.

5.2 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

DELAFLOXACIN

5.3.2 FDA UNII

6315412YVF

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Fluoroquinolones

5.4 ATC Code

J01MA23

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01M - Quinolone antibacterials

J01MA - Fluoroquinolones

J01MA23 - Delafloxacin

5.5 Absorption, Distribution and Excretion

Absorption

The median time to peak plasma concentration for orally administered Delafloxacin is 0.75 (0.5-4.0) hours after a single dose and 1.00 (0.5-6.0) hours for steady state dosing. The median time to peak plasma concentration for intravenously administered Delafloxacin is 1.00 (1.0-1.2) hours for a single dose and 1.0 (1.0-1.0) hour for steady state dosing. The absolute bioavailability for orally administed Delafloxacin is 58.8%.

Route of Elimination

After a single intravenous dose, 65% of Delafloxacin was excreted in the urine either unchanged or as glucuronide metabolites with 28% excreted unchanged in the feces. After a single oral dose, 50% of Delafloxacin was excreted in the urine either unchanged or as glucuronide metabolites with 48% excreted unchanged in the feces.

Volume of Distribution

The steady sate volume of distrubution of Delafloxacin is 30-48 liters.

Clearance

The mean total clearance of Delafloxacin is 16.3 liters per hour. Renal clearance accounts for 35-45% of total clearance.

5.6 Metabolism/Metabolites

Delafoxacin is primarily metabolized via glucuronidation mediated by UDP glucuronosyltransferase 1-1, UDP-glucuronosyltransferase 1-3, and UDP-glucuronosyltransferase 2B15. Less than 1% is metabolized via oxidation.

5.7 Biological Half-Life

The mean half life of elimination of Delafloxacin is 3.7 hours after a single intravenous administration. The mean half life of elimination for multple oral administrations is 4.2-8.5 hours.

5.8 Mechanism of Action

Delafloxacin inhibits the activity of bacterial DNA topoisomerase IV and DNA gyrase (topoisomerase II). This interferes with bacterial DNA replication by preventing the relaxation of positive supercoils introduced as part of the elongation process. The resultant strain inhibits further elongation. Delafloxacin exerts concentration-dependent bacteriocidal activity.

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