Identification
- Summary
Ozenoxacin is a quinolone antibiotic used to treat impetigo caused by susceptible bacteria.
- Brand Names
- Ozanex
- Generic Name
- Ozenoxacin
- DrugBank Accession Number
- DB12924
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Ozenoxacin (DB12924)
- Weight
- Average: 363.417
Monoisotopic: 363.158291548 - Chemical Formula
- C21H21N3O3
- Synonyms
- Ozenoxacin
- Ozenoxacino
Pharmacology
- 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 Label.
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- Contraindications & Blackbox Warnings
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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 1.
- 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 Label.
As DNA gyrase A and topoisomerase IV are essential to bacterial DNA replication activities including supercoiling, supercoil relaxation, chromosomal condensation, chromosomal decatenation 2 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 Label.
Target Actions Organism ADNA gyrase subunit A inhibitorHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) ADNA topoisomerase 4 subunit A inhibitorEscherichia coli (strain K12) - 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 Label,1.
- Volume of distribution
Ozenoxacin undergoes negligible systemic absorption after its topical administration Label. Subsequently, since negligible systemic absorption of ozenoxacin was observed in clinical studies, tissue distribution has not been investigated in humans either Label.
- Protein binding
The plasma protein binding of [14 C]-ozenoxacin is moderate at ~80-85% and does not appear to be dependent on concentration Label.
- Metabolism
Studies have demonstrated that ozenoxacin is not metabolized in the presence of fresh human skin discs and is minimally metabolized in human hepatocytes Label.
- 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 Label.
- Half-life
Not Available
- Clearance
Ozenoxacin undergoes negligible systemic absorption after its topical administration Label.
- Adverse Effects
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Ozenoxacin cream has the potential to cause rosacea and seborrheic dermatitis when administered topically on a patient. In clinical trials, only one adult patient treated with ozenoxacin cream reported such adverse reactions Label.
Much like other topical antibiotics, the prolonged use of ozenoxacin cream can result in the overgrowth of nonsusceptible bacteria and fungi. If such overgrowths develop into infections during therapy, discontinue use of the ozenoxacin cream and institue appropriate therapy for the infections Label.
Although clinical studies demonstrate negligible systemic absorption after topical administration of ozenoxacin, there are no formal available data on the use of ozenoxacin in pregnant women to inform any professional drug associated risk for use in pregnancy Label.
Although breastfeeding is not expected to result in exposure of the child to ozenoxacin owing to the negligible systemic absorption of ozenoxacin in humans following topical administration, no formal data are available regarding the presence of ozenoxacin in human milk and the effects of ozenoxacin on breasfed infants or on milk production Label.
Clinical experience with ozenoxacin cream has not identified differences in responses between elderly and younger patients Label.
The safety and effectiveness of ozenoxacin cream in pediatric patients 2 months and older is similar to that of adults, but the safety and effectiveness of ozenoxacin in pediatric patients younger than 2 months of age has not been formally establlished Label.
Long-term studies in animals to evaluate carcinogenic potential have not been conducted with ozenoxacin Label.
Ozenoxacin demonstrated no genotoxicity when evaluated in vitro for gene mutation and/or chromosomal effects in the Ames test, mouse lymphoma cell assay, or when evaluated in vivo in a rat micronucleus test with demonstrated systemic exposure Label.
Oral doses of ozenoxacin did not affect mating and fertility in male and female rats treated up to 500 mg/kg/day (about 8500 and 16,000 times respectively, the maximum human plasma concentration seen with dermal application of ozenoxacin 1% cream) Label.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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interactions in your softwareEstetrol The therapeutic efficacy of Estetrol can be decreased when used in combination with Ozenoxacin. Fecal microbiota The therapeutic efficacy of Fecal microbiota can be decreased when used in combination with Ozenoxacin. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ozanex Cream 1 % w/w Topical Ferrer Internacional S.A. 2018-01-04 Not applicable Canada 
Xepi Cream 10 mg/1g Topical Cutanea Life Sciences, Inc. 2018-10-05 Not applicable US 
Xepi Cream 10 mg/1g Topical Medimetriks Pharmaceuticals, Inc. 2017-12-15 2018-02-02 US Xepi Cream 10 mg/1g Topical Biofrontera Inc. 2019-12-19 Not applicable US
Categories
- ATC Codes
- D06AX14 — Ozenoxacin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Quinoline carboxylic acids
- Direct Parent
- Quinoline carboxylic acids
- Alternative Parents
- Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Methylpyridines / Aminopyridines and derivatives / Imidolactams / Benzenoids / Vinylogous amides / Heteroaromatic compounds / Carboxylic acids show 5 more
- Substituents
- Amine / Aminopyridine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Dihydroquinoline / Dihydroquinolone / Heteroaromatic compound show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- V0LH498RFO
- CAS number
- 245765-41-7
- InChI Key
- XPIJWUTXQAGSLK-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 1-cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)pyridin-3-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
- SMILES
- CNC1=NC=C(C=C1C)C1=CC=C2C(=O)C(=CN(C3CC3)C2=C1C)C(O)=O
References
- General References
- Gropper S, Albareda N, Santos B, Febbraro S: Systemic bioavailability, safety and tolerability of topical ozenoxacin in healthy adult volunteers. Future Microbiol. 2014;9(8 Suppl):S11-6. doi: 10.2217/fmb.14.82. [Article]
- Fabrega A, Madurga S, Giralt E, Vila J: Mechanism of action of and resistance to quinolones. Microb Biotechnol. 2009 Jan;2(1):40-61. doi: 10.1111/j.1751-7915.2008.00063.x. Epub 2008 Oct 13. [Article]
- External Links
- PubChem Compound
- 9863827
- PubChem Substance
- 347829069
- ChemSpider
- 8039521
- 1994739
- ChEBI
- 136050
- ChEMBL
- CHEMBL3990047
- ZINC
- ZINC000001483896
- Wikipedia
- Ozenoxacin
- FDA label
- Download (308 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Cream Topical 1 % w/w Cream Topical 10 mg/1g - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9180200 No 2015-11-10 2032-01-29 US US9399014 No 2016-07-26 2029-12-15 US US6335447 No 2002-01-01 2019-04-06 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.103 mg/mL ALOGPS logP 2.76 ALOGPS logP 2.54 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 6.1 Chemaxon pKa (Strongest Basic) 6.77 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 82.53 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 106.11 m3·mol-1 Chemaxon Polarizability 39.71 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dna topoisomerase type ii (atp-hydrolyzing) activity
- Specific Function
- DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
- Gene Name
- gyrA
- Uniprot ID
- P43700
- Uniprot Name
- DNA gyrase subunit A
- Molecular Weight
- 97817.145 Da
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dna topoisomerase type ii (atp-hydrolyzing) activity
- Specific Function
- Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule. MukB stimulates th...
- Gene Name
- parC
- Uniprot ID
- P0AFI2
- Uniprot Name
- DNA topoisomerase 4 subunit A
- Molecular Weight
- 83830.455 Da
Drug created at October 21, 2016 01:20 / Updated at May 31, 2023 00:21