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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
Structure of OXICONAZOLE NITRATE

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+;

HIDE SMILES / InChI

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
OXISTAT
Curative
OXISTAT
Curative
OXISTAT
Curative
OXISTAT

Cmax

ValueDoseCo-administeredAnalytePopulation
635 ng/mL
1 % 2 times / day multiple, topical
OXICONAZOLE nail
Homo sapiens
95.12 μg/mL
1 % single, topical
OXICONAZOLE plasma
Rattus norvegicus

AUC

ValueDoseCo-administeredAnalytePopulation
1160 ng × week/mg
1 % 2 times / day multiple, topical
OXICONAZOLE nail
Homo sapiens
223.18 μg × h/mL
1 % single, topical
OXICONAZOLE plasma
Rattus norvegicus

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
OXICONAZOLE unknown
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
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
The MIC90 of Oxiconazole against C. albicans and C. glabrata isolates were 0.12 and 0.25 μg/ml respectively.