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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13Cl4N3O
Molecular Weight 429.127
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OXICONAZOLE

SMILES

ClC1=CC(Cl)=C(CO\N=C(/CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

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: 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.

Originator

Approval Year

1988
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
Approved
8429
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
Approved
8429
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
Approved
8429
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
REVIEW
https://books.google.ru/books?id=Bw7MBQAAQBAJ&pg=PA201&lpg=PA201&dq=OXICONAZOLE+auc&source=bl&ots=8jqe8Z_yRv&sig=ACfU3U17TASx7dLz-CCSZUXreFaVrPmdDg&hl=en&sa=X&ved=2ahUKEwil3s2u5I3sAhXxk4sKHRGjDmYQ6AEwEnoECAEQAQ#v=onepage&q=OXICONAZOLE%20auc&f=false
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
EXPERIMENT
https://www.researchgate.net/publication/329485879_FORMULATION_AND_EVALUATION_OF_OXICONAZOLE_BASED_NIOSOMAL_GEL_FOR_THE_EFFECTIVE_FUNGAL_TREATMENT
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
REVIEW
https://books.google.ru/books?id=Bw7MBQAAQBAJ&pg=PA201&lpg=PA201&dq=OXICONAZOLE+auc&source=bl&ots=8jqe8Z_yRv&sig=ACfU3U17TASx7dLz-CCSZUXreFaVrPmdDg&hl=en&sa=X&ved=2ahUKEwil3s2u5I3sAhXxk4sKHRGjDmYQ6AEwEnoECAEQAQ#v=onepage&q=OXICONAZOLE%20auc&f=false
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
EXPERIMENT
https://www.researchgate.net/publication/329485879_FORMULATION_AND_EVALUATION_OF_OXICONAZOLE_BASED_NIOSOMAL_GEL_FOR_THE_EFFECTIVE_FUNGAL_TREATMENT
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/30210010
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205076Orig1s000lbl.pdf
unhealthy, adult
n = 955
Health Status: unhealthy
Condition: skin infections
Age Group: adult
Sex: unknown
Population Size: 955
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205076Orig1s000lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205076Orig1s000lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

inducer
781
inducer
389

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
701

CYP2B6
547
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
PXR
46
 yes [EC50 6.1 uM]
CYP3A4
1925
 yes [IC50 0.8 uM]
CYP1A2
1692
 yes
CYP2B6
1001
 yes
CYP2C9
1819
 yes
CYP3A4
1925
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7825
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7825
ChemicalBook
CB6394620
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6394620
ZINC
ZINC000003873295
http://zinc15.docking.org/substances/ZINC000003873295
eMolecules
902250
https://www.emolecules.com/cgi-bin/more?vid=902250
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
AroER tri-screen is a biologically relevant assay for endocrine disrupting chemicals modulating the activity of aromatase and/or the estrogen receptor.
2014 May
Patents

Patents

WO/1992/014472A1
2
WO/2012/023079A1
2

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.
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 [WHO-DD]
Common Name English
OXICONAZOLE [MI]
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 Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
NDF-RT N0000008217
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
WHO-VATC QG01AF17
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
WHO-ATC G01AF17
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
WHO-ATC D01AC11
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
WHO-VATC QD01AC11
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C61869
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
DRUG BANK
DB00239
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
DAILYMED
C668Q9I33J
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
RXCUI
32638
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8040690
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
SMS_ID
100000083041
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
CHEBI
7825
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
DRUG CENTRAL
3408
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
PUBCHEM
5353853
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
CAS
64211-45-6
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
LACTMED
Oxiconazole
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
EVMPD
SUB09523MIG
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
MERCK INDEX
m8306
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY Merck Index
FDA UNII
C668Q9I33J
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
INN
4729
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
MESH
C022155
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
WIKIPEDIA
OXICONAZOLE
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL1262
Created by admin on Fri Dec 15 15:51:35 GMT 2023 , Edited by admin on Fri Dec 15 15:51:35 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of OXICONAZOLE
SALT/SOLVATE (PARENT)
Structure of OXICONAZOLE NITRATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
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