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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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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

1988
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

1988
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

1988
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

1988
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
n = 955
Health Status: unhealthy
Condition: skin infections
Age Group: adult
Sex: unknown
Population Size: 955
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


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 NITRATE
JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   WHO-DD  
USAN  
Official Name English
RO 13-8996
Code English
SGD-301-76
Code English
SGD 301-76
Code English
OXICONAZOLE NITRATE [JAN]
Common Name English
ST-813
Code English
OXISTAT
Brand Name English
ETHANONE, 1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)-, O-((2,4-DICHLOROPHENYL)METHYL)OXIME, (Z)-, MONONITRATE
Common Name English
NSC-758958
Code English
OXICONAZOLE NITRATE [MART.]
Common Name English
RO-13-8996
Code English
OXICONAZOLE NITRATE [USAN]
Common Name English
2',4'-DICHLORO-2-IMIDAZOL-1-YLACETOPHENONE (Z)-(O-(2,4-DICHLOROBENZYL)OXIME), MONONITRATE
Systematic Name English
OXICONAZOLE NITRATE [MI]
Common Name English
OXICONAZOLE NITRATE [ORANGE BOOK]
Common Name English
Oxiconazole nitrate [WHO-DD]
Common Name English
OXICONAZOLE NITRATE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
Code System Code Type Description
USAN
Z-1
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY
DAILYMED
RQ8UL4C17S
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY
CHEBI
7826
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY
NSC
758958
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY
FDA UNII
RQ8UL4C17S
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY
SMS_ID
100000092637
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PRIMARY
NCI_THESAURUS
C47644
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
264-730-3
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PRIMARY
EVMPD
SUB03569MIG
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PRIMARY
CAS
64211-46-7
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PRIMARY
EPA CompTox
DTXSID2045943
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PRIMARY
CHEBI
7825
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PRIMARY
DRUG BANK
DB00239
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PRIMARY
PUBCHEM
9556529
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PRIMARY
ChEMBL
CHEMBL1262
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PRIMARY
RXCUI
56226
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m8306
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1483425
Created by admin on Fri Dec 15 15:13:39 GMT 2023 , Edited by admin on Fri Dec 15 15:13:39 GMT 2023
PRIMARY