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Also known as: 245765-41-7, Xepi, T-3912, T 3912, 1-cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)pyridin-3-yl]-4-oxoquinoline-3-carboxylic acid, Gf-001001-00
Molecular Formula
C21H21N3O3
Molecular Weight
363.4  g/mol
InChI Key
XPIJWUTXQAGSLK-UHFFFAOYSA-N
FDA UNII
V0LH498RFO

Ozenoxacin
To date, ozenoxacin has been used in trials studying the treatment of impetigo. As of December 11, 2017 the FDA approved Ferrer Internacional S.A.'s Xepi (ozenoxacin 1%) as a topically applied cream indicated for the treatment of impetigo caused by *Staphylococccus aureus* or *Streptococcus pyogenes* in adult and pediatric patients 2 months of age and older. Despite being a common and highly contagious bacerial skin infection that affects millions of children and adults in the United States each year, ozenoxacin cream is a novel, non-fluorinated quinolone that has demonstrated safe and effective therapy in both the adult and pediatric population.
Ozenoxacin is a Quinolone Antimicrobial.
1 2D Structure

Ozenoxacin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)pyridin-3-yl]-4-oxoquinoline-3-carboxylic acid
2.1.2 InChI
InChI=1S/C21H21N3O3/c1-11-8-13(9-23-20(11)22-3)15-6-7-16-18(12(15)2)24(14-4-5-14)10-17(19(16)25)21(26)27/h6-10,14H,4-5H2,1-3H3,(H,22,23)(H,26,27)
2.1.3 InChI Key
XPIJWUTXQAGSLK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=CN=C1NC)C2=C(C3=C(C=C2)C(=O)C(=CN3C4CC4)C(=O)O)C
2.2 Other Identifiers
2.2.1 UNII
V0LH498RFO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-cyclopropyl-8-methyl-7-(5-methyl-6-(methylamino)-3-pyridinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic Acid

2. Ozanex

3. Xepi

2.3.2 Depositor-Supplied Synonyms

1. 245765-41-7

2. Xepi

3. T-3912

4. T 3912

5. 1-cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)pyridin-3-yl]-4-oxoquinoline-3-carboxylic Acid

6. Gf-001001-00

7. V0lh498rfo

8. 1-cyclopropyl-8-methyl-7-(5-methyl-6-(methylamino)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

9. Ozenoxacin Cream

10. Ozenoxacin [inn]

11. Ozenoxacin [inn:jan]

12. Unii-v0lh498rfo

13. Ozadub

14. Xepi (tn)

15. Ozenoxacin [mi]

16. Ozenoxacin; T-3912

17. Ozenoxacin [jan]

18. Ozenoxacin [usan]

19. Ozenoxacin [who-dd]

20. Ozenoxacin (jan/usan/inn)

21. Schembl1711829

22. Chembl3990047

23. Ozenoxacin [orange Book]

24. Gtpl10841

25. Dtxsid00947446

26. Chebi:136050

27. Bcp16621

28. Ex-a2693

29. Vja76541

30. Who 8788

31. Zinc1483896

32. S6582

33. Akos032947315

34. At18754

35. Db12924

36. Sb16801

37. Ncgc00532517-01

38. Bs-16742

39. Da-31712

40. Hy-14957

41. Ozenoxacin 100 Microg/ml In Acetonitrile

42. Cs-0003657

43. Ft-0701296

44. D09544

45. Q17125399

46. Gf-001001-00; M-5120; T-3912; Gf-00100100;t3912;t 3912

47. 1-cyclopropyl-8-methyl-7-(5-methyl-6-(methylamino)-3-pyridinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic Acid

48. 3-quinolinecarboxylic Acid, 1-cyclopropyl-1,4-dihydro-8-methyl-7-(5-methyl-6-(methylamino)-3-pyridinyl)-4-oxo-

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 363.4 g/mol
Molecular Formula C21H21N3O3
XLogP34.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass363.15829154 g/mol
Monoisotopic Mass363.15829154 g/mol
Topological Polar Surface Area82.5 Ų
Heavy Atom Count27
Formal Charge0
Complexity645
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 Indication

Ozenoxacin cream is indicated for the topical treatment of impetigo caused by *Staphylococcus aureus* or *Streptococcus pyogenes* in patients aged 2 months of age and older.


FDA Label


Treatment of impetigo


5 Pharmacology and Biochemistry
5.1 Pharmacology

Although the exposure response relationship for ozenoxacin after it has been applied topically has not yet been studied, a formal relationship is unlikely because systemic exposure of ozenoxacin following its topical application has been measured to be negligible.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


Topoisomerase Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASES. (See all compounds classified as Topoisomerase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
OZENOXACIN
5.3.2 FDA UNII
V0LH498RFO
5.3.3 Pharmacological Classes
Quinolones [CS]; Quinolone Antimicrobial [EPC]
5.4 ATC Code

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AX - Other antibiotics for topical use

D06AX14 - Ozenoxacin


5.5 Absorption, Distribution and Excretion

Absorption

Four studies were performed in which varying strengths of ozenoxacin cream, up to 2% (twice the concentration of the marketed formulation), were administered to 110 patients. Three of the studies examined systemic absorption in healthy subjects and in subjects having impetigo. The studies were performed with either single or repeated application of up to 1 g ozenoxacin cream to intact or abraded skin (up to 200 cm squared surface area). No systemic absorption was seen in 84 of 86 subjects, and negligible systemic absorption was seen at the level of detection (0.489 ng/mL) in 2 subjects.


Route of Elimination

Studies regarding elimination and excretion have not yet been investigated in humans due to the negligible systemic absorption observed in clinical studies.


Volume of Distribution

Ozenoxacin undergoes negligible systemic absorption after its topical administration. Subsequently, since negligible systemic absorption of ozenoxacin was observed in clinical studies, tissue distribution has not been investigated in humans either.


Clearance

Ozenoxacin undergoes negligible systemic absorption after its topical administration.


5.6 Metabolism/Metabolites

Studies have demonstrated that ozenoxacin is not metabolized in the presence of fresh human skin discs and is minimally metabolized in human hepatocytes.


5.7 Mechanism of Action

Ozenoxacin is a quinolone antibiotic drug. And, like most quinolones, ozenoxacin predominately executes its mechanism of action by entering into bacterial cells and acting to inhibit the bacterial DNA replication enzymes DNA gyrase A and topoisomerase IV. As DNA gyrase A and topoisomerase IV are essential to bacterial DNA replication activities including supercoiling, supercoil relaxation, chromosomal condensation, chromosomal decatenation and more, their inhibition is the principal action of ozenoxacin's mechanism and it has been demonstrated to be bactericidal against *S. aureus* and *S. pyogenes* organisms.


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02-Mar-2021
24-Sep-2024
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