Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H13Cl4N3O.HNO3 |
Molecular Weight | 492.14 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.ClC1=CC(Cl)=C(CO\N=C(/CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1
InChI
InChIKey=WVNOAGNOIPTWPT-NDUABGMUSA-N
InChI=1S/C18H13Cl4N3O.HNO3/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22;2-1(3)4/h1-8,11H,9-10H2;(H,2,3,4)/b24-18+;
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/7037014Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2029718/
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b87a89d2-6e45-4eb8-be2c-7f55f34d61e5
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7037014
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2029718/
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b87a89d2-6e45-4eb8-be2c-7f55f34d61e5
Oxiconazole nitrate is 2',4'-dichloro-2-imidazol-1-ylacetophenone (Z)-[0-(2,4-dichlorobenzyl)oxime], mononitrate is an imidazole derivative characterized by a broad fungistatic spectrum. In vitro oxiconazole is highly effective against many dermatophytes, including Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, and Epidermophyton floccosum. In addition, fungicidal activity of various degree was found in selected species (Aspergillus fumigatus, Cryptococcus neoformans, Candida albicans and Trichophyton mentagrophytes). Synthesis of DNA was inhibited by subinhibitory concentrations of oxiconazole in parallel to cell multiplication, whereas synthesis of RNA, protein and carbohydrate was decreased to a lesser extent. OXISTAT® (Oxiconazole nitrate) Cream and Lotion are indicated for the topical treatment of the following dermal infections: tinea pedis, tinea cruris, and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes, or Epidermophyton floccosum. OXISTAT® Cream is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur. Oxiconazole cream exerts no detectable systemic effect since only a negligible amount is absorbed from the skin. Once-daily use of oxiconazole cream could be valuable in patients with a history of noncompliance with multiple-daily regimens of other topical antifungal agents.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map00100 Sources: http://www.genome.jp/dbget-bin/www_bget?D08313 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | OXISTAT Approved UseOXISTAT® Cream and Lotion are indicated for the topical treatment of the following dermal infections: tinea pedis, tinea cruris, and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes, or Epidermophyton floccosum. OXISTAT® Cream is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES). OXISTAT® Cream may be used in pediatric patients for tinea corporis, tinea cruris, tinea pedis, and tinea (pityriasis) versicolor; however, these indications for which OXISTAT® Cream has been shown to be effective rarely occur in children below the age of 12. Launch Date1988 |
|||
Curative | OXISTAT Approved UseOXISTAT® Cream and Lotion are indicated for the topical treatment of the following dermal infections: tinea pedis, tinea cruris, and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes, or Epidermophyton floccosum. OXISTAT® Cream is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES). OXISTAT® Cream may be used in pediatric patients for tinea corporis, tinea cruris, tinea pedis, and tinea (pityriasis) versicolor; however, these indications for which OXISTAT® Cream has been shown to be effective rarely occur in children below the age of 12. Launch Date1988 |
|||
Curative | OXISTAT Approved UseOXISTAT® Cream and Lotion are indicated for the topical treatment of the following dermal infections: tinea pedis, tinea cruris, and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes, or Epidermophyton floccosum. OXISTAT® Cream is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES). OXISTAT® Cream may be used in pediatric patients for tinea corporis, tinea cruris, tinea pedis, and tinea (pityriasis) versicolor; however, these indications for which OXISTAT® Cream has been shown to be effective rarely occur in children below the age of 12. Launch Date1988 |
|||
Curative | OXISTAT Approved UseOXISTAT® Cream and Lotion are indicated for the topical treatment of the following dermal infections: tinea pedis, tinea cruris, and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes, or Epidermophyton floccosum. OXISTAT® Cream is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES). OXISTAT® Cream may be used in pediatric patients for tinea corporis, tinea cruris, tinea pedis, and tinea (pityriasis) versicolor; however, these indications for which OXISTAT® Cream has been shown to be effective rarely occur in children below the age of 12. Launch Date1988 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
635 ng/mL |
1 % 2 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered: |
OXICONAZOLE nail | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
95.12 μg/mL |
1 % single, topical dose: 1 % route of administration: Topical experiment type: SINGLE co-administered: |
OXICONAZOLE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1160 ng × week/mg |
1 % 2 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered: |
OXICONAZOLE nail | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
223.18 μg × h/mL |
1 % single, topical dose: 1 % route of administration: Topical experiment type: SINGLE co-administered: |
OXICONAZOLE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30210010 |
OXICONAZOLE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/17998298/ Page: - |
yes [EC50 6.1 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29991575/ Page: - |
yes [IC50 0.8 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Patents
Sample Use Guides
OXISTAT® (oxiconazole nitrate) Cream or Lotion 1% should be applied to affected and immediately surrounding areas once to twice daily in patients with tinea pedis, tinea corporis, or tinea cruris. OXISTAT® Cream should be applied once daily in the treatment of tinea (pityriasis) versicolor. Tinea corporis, tinea cruris, and tinea (pityriasis) versicolor should be treated for 2 weeks and tinea pedis for 1 month to reduce the possibility of recurrence.
Route of Administration:
Transdermal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26627336
The MIC90 of Oxiconazole against C. albicans and C. glabrata isolates were 0.12 and 0.25 μg/ml respectively.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C514
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56226
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m8306
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1483425
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ACTIVE MOIETY
SUBSTANCE RECORD