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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
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 Weight 440.8 g/mol
Molecular Formula C18H12ClF3N4O4
XLogP32.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count11
Rotatable Bond Count3
Exact Mass440.0499171 g/mol
Monoisotopic Mass440.0499171 g/mol
Topological Polar Surface Area120 Ų
Heavy Atom Count30
Formal Charge0
Complexity755
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 1  
Drug NameBAXDELA
Active IngredientDELAFLOXACIN MEGLUMINE
CompanyMELINTA 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


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.


API Reference Price

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21-Jun-2021
13-Feb-2024
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