Clinical data | |
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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 |
ATC code | |
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CAS Number | |
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ChEBI | |
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CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C21H21N3O3 |
Molar mass | 363.417 g·mol−1 |
3D model ( JSmol) | |
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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).
Clinical data | |
---|---|
Pronunciation | oz en ox' a sin |
Trade names | Ozanex; Xepi |
AHFS/ Drugs.com | Monograph |
MedlinePlus | a618010 |
License data |
|
Routes of administration | Topical |
ATC code | |
Legal status | |
Legal status | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C21H21N3O3 |
Molar mass | 363.417 g·mol−1 |
3D model ( JSmol) | |
| |
|
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).