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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13Cl4N3O
Molecular Weight 429.1277
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OXICONAZOLE

SMILES

c1cc(cc(c1CO/N=C(\Cn2ccnc2)/c3ccc(cc3Cl)Cl)Cl)Cl

InChI

InChIKey=QRJJEGAJXVEBNE-HKOYGPOVSA-N
InChI=1S/C18H13Cl4N3O/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/h1-8,11H,9-10H2/b24-18+

HIDE SMILES / InChI

Description
Curator's Comment:: 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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
OXISTAT

Approved Use

OXISTAT® 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 Date

599443200000
Curative
OXISTAT

Approved Use

OXISTAT® 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 Date

599443200000
Curative
OXISTAT

Approved Use

OXISTAT® 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 Date

599443200000
Curative
OXISTAT

Approved Use

OXISTAT® 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 Date

599443200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
OXICONAZOLE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % multiple, topical
Highest studied dose
Dose: 1 %
Route: topical
Route: multiple
Dose: 1 %
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
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
The MIC90 of Oxiconazole against C. albicans and C. glabrata isolates were 0.12 and 0.25 μg/ml respectively.
Name Type Language
OXICONAZOLE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ETHANONE, 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-, O-((2,4-DICHLOROPHENYL)METHYL)OXIME, (Z)-
Common Name English
OXICONAZOLE [INN]
Common Name English
OXICONAZOLE [VANDF]
Common Name English
OXICONAZOLE [MI]
Common Name English
OXICONAZOLE [WHO-DD]
Common Name English
2',4'-DICHLORO-2-IMIDAZOL-1-YLACETOPHENONE (Z)-(O-(2,4-DICHLOROBENZYL)OXIME)
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175487
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
NDF-RT N0000008217
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
WHO-VATC QG01AF17
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
WHO-ATC G01AF17
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
NCI_THESAURUS C514
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
WHO-ATC D01AC11
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
WHO-VATC QD01AC11
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C61869
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
DRUG BANK
DB00239
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
RXCUI
32638
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY RxNorm
EPA CompTox
64211-45-6
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
DRUG CENTRAL
3408
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
PUBCHEM
5353853
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
CAS
64211-45-6
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
LACTMED
Oxiconazole
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
EVMPD
SUB09523MIG
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
MERCK INDEX
M8306
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY Merck Index
FDA UNII
C668Q9I33J
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
INN
4729
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
MESH
C022155
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
WIKIPEDIA
OXICONAZOLE
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY
ChEMBL
CHEMBL1262
Created by admin on Sat Jun 26 04:45:13 UTC 2021 , Edited by admin on Sat Jun 26 04:45:13 UTC 2021
PRIMARY