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| Pronunciation | oz en ox' a sin |
| Trade names | Ozanex; Xepi |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a618010 |
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| Routes of administration | Topical |
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| Chemical and physical data | |
| Formula | C21H21N3O3 |
| Molar mass | 363.417 g·mol−1 |
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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]
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]
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).
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| Antifolates (inhibit bacterial purine metabolism, thereby inhibiting DNA and RNA synthesis) |
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| Quinolones (inhibit bacterial topoisomerase and/or DNA gyrase, thereby inhibiting DNA replication) |
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| Anaerobic DNA inhibitors |
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| RNA synthesis |
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