Ozenoxacin

Source: Wikipedia, the free encyclopedia.
Ozenoxacin
Clinical data
Pronunciationoz en ox' a sin
Trade namesOzanex; Xepi
AHFS/Drugs.comMonograph
MedlinePlusa618010
License data
Routes of
administration		Topical
ATC code
Legal status
Legal status
Identifiers
  • 1-Cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)-3-pyridinyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
JSmol)
  • O=C\3c1c(c(c(cc1)c2cc(c(nc2)NC)C)C)N(/C=C/3C(=O)O)C4CC4
  • 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)
  • Key:XPIJWUTXQAGSLK-UHFFFAOYSA-N

Ozenoxacin, sold under the brand names Ozanex and Xepi, is a quinolone antibiotic used for the treatment of impetigo.[4] A 1% topical cream is approved for treatment of impetigo in Canada[5] and in the United States.[6][7]

Ozenoxacin is active against some bacteria that have developed resistance to

fluoroquinolone antibiotics.[8]

Mechanism of Action

Like other quinolone antibiotics, ozenoxacin targets DNA gyrase and topoisomerase IV.[9]

Its activity against bacteria with fluoroquinolone resistance is attributed to its evasion of bacterial efflux pumps.[8]

Chemistry

Synthesis

Synthesis of Ozenoxacin

Ozenoxacin is synthesized by the Pd-catalyzed cross-coupling of a bromoquinolone and a pyridyl tributylstannane (Stille coupling).[10][11]

The pyridyl tributylstannane is synthesized from the corresponding dihalopyridine. This is achieved through a sequence of nucleophilic aromatic substitution with methylamine, which is protected as the acetamide using acetic anhydride and this is converted to the organostannane through a Pd-catalyzed stannylation with bis(tributyltin).

The bromoquinolone is made from the N-cyclopropyl aniline and diethyl ethoxymethylenemalonate, which react through a Michael addition, followed by elimination of the ethoxy group and then a Friedel-Crafts acylation at elevated temperature. The N-cyclopropyl aniline is prepared by a Pd-catalyzed cross coupling of 2,6-dibromotoluene and cyclopropylamine (Buchwald-Hartwig coupling).

References

  1. ^ "Skin health". Health Canada. 9 May 2018. Retrieved 13 April 2024.
  2. ^ "Xepi- ozenoxacin cream". DailyMed. 30 January 2020. Retrieved 13 October 2020.
  3. ^ https://www.ema.europa.eu/documents/psusa/ozenoxacin-list-nationally-authorised-medicinal-products-psusa/00010651/202205_en.pdf [bare URL PDF]
  4. ^ "Ozenoxacin". PubChem. U.S. National Library of Medicine. Retrieved 2019-01-10.
  5. ^ "Cipher Pharmaceuticals Receives Health Canada Approval of Ozanex (ozenoxacin cream 1%)" (Press release). Cipher Pharmaceuticals Inc.
  6. ^ "Medimetriks Pharmaceuticals, Inc. Receives FDA Approval for Xepi (ozenoxacin) Cream, 1%, a Novel Topical Antibiotic for Impetigo" (Press release). Medimetriks Pharmaceuticals, Inc. – via PRNewswire.
  7. ^ "Xepi (ozenoxacin) Cream". U.S. Food and Drug Administration (FDA). 18 January 2018. Retrieved 13 October 2020.
  8. ^
    PMID 24080666
    .
  9. S2CID 205850659
    .
  10. ^ US 6335447, Hayashi K, Kito T, Mitsuyama J, Yamakawa T, Kuroda H, Kawafuchi H, "Quinolonecarboxylic acid derivatives or salts thereof", issued 2002-01-01, assigned to Toyama Chemical Co Ltd 
  11. PMID 28421763
    .
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