OXICONAZOLE NITRATE

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 Search

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

Molecular Formula	HNO3
Molecular Weight	63.0128
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H13Cl4N3O
Molecular Weight	429.127
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Steroid biosynthesis 3 Target ID: map00100 Sources: http://www.genome.jp/dbget-bin/www_bget?D08313	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Tinea pedis 28 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b87a89d2-6e45-4eb8-be2c-7f55f34d61e5	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
Tinea cruris 11 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b87a89d2-6e45-4eb8-be2c-7f55f34d61e5	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
Tinea corporis 19 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b87a89d2-6e45-4eb8-be2c-7f55f34d61e5	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
Tinea (pityriasis) versicolor 2 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b87a89d2-6e45-4eb8-be2c-7f55f34d61e5	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

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

Doses

Dose	Population	Adverse 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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 inducer 781	inducer 389

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity
PXR 46	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/17998298/ Page: -	yes [EC50 6.1 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/29991575/ Page: -	yes [IC50 0.8 uM]
CYP1A2 1692	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: -	yes
CYP2B6 1001	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: -	yes
CYP2C9 1819	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: -	yes
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/27208383/ Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903
AroER tri-screen is a biologically relevant assay for endocrine disrupting chemicals modulating the activity of aromatase and/or the estrogen receptor.	2014 May	24496634

Patents

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:39 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:39 GMT 2023`
Record UNII	RQ8UL4C17S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXICONAZOLE NITRATE

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