SERTACONAZOLE NITRATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H15Cl3N2OS.HNO3
Molecular Weight	500.783
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[N+]([O-])=O.ClC1=CC=C(C(CN2C=CN=C2)OCC3=CSC4=C3C=CC=C4Cl)C(Cl)=C1

InChI

InChIKey=HAAITRDZHUANGT-UHFFFAOYSA-N

InChI=1S/C20H15Cl3N2OS.HNO3/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22;2-1(3)4/h1-8,11-12,19H,9-10H2;(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula	C20H15Cl3N2OS
Molecular Weight	437.77
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021385s005lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/ertaczo-drug.htm https://www.drugs.com/mtm/sertaconazole-topical.html http://www.wikidoc.org/index.php/Sertaconazole

Sertaconazole is a azole antifungal that is FDA approved for the treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by: Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum. Sertaconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Common adverse reactions include contact dermatitis, dry skin, burning skin and application site skin tenderness.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021385s005lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/19275277	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Interdigital tinea pedis 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021385s005lbl.pdf	Curative		Approved 8583	ERTACZO Approved Use ERTACZO® (sertaconazole nitrate) Cream, 2%, is indicated for the topical treatment of interdigital tinea pedis in immunocompetent patients 12 years of age and older, caused by: Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum (see CLINICAL STUDIES Section). Launch Date 2003

C_max

Value	Dose	Co-administered	Analyte	Population
1.79 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19889586	300 mg single, vaginal dose: 300 mg route of administration: Vaginal experiment type: SINGLE co-administered:		SERTACONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
43.31 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19889586	300 mg single, vaginal dose: 300 mg route of administration: Vaginal experiment type: SINGLE co-administered:		SERTACONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
20.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19889586	300 mg single, vaginal dose: 300 mg route of administration: Vaginal experiment type: SINGLE co-administered:		SERTACONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% OTHER https://go.drugbank.com/drugs/DB01153			SERTACONAZOLE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 % 2 times / day steady, topical Highest studied dose Dose: 2 %, 2 times / day Route: topical Route: steady Dose: 2 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021385s005lbl.pdf	healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021385s005lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021385s005lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY583730	https://www.001chemical.com/chem/99592-32-2
AA Blocks	AA0064TQ	https://www.aablocks.com/goods/Goods/detail?id=AA0064TQ
abcr GmbH	AB417540	http://www.abcr.com/shop/en/AB417540
Acadechem	ACDC-063581	http://acadechemical.com/product/5745
Alichem	69002988	http://www.alichem.com/en/products/99592-32-2.html
Alinda	ALBB-028957	http://alinda.ru/finechem_en_.html?i=ALBB-028957
Alsachim	2573	http://www.alsachim.com/product-C3634-glo.bal-view.html
Angene	AGN-PC-0W9MAR	http://www.angenechemical.com/productshow/AGN-PC-0W9MAR.html
BioChemPartner	BCP12180	http://www.biochempartner.com/99592-32-2-BCP12180
BioCrick	BCC9146	http://www.biocrick.com/Sertaconazole-BCC9146.html
BLD Pharm	BD42151	http://www.bldpharm.com/products/99592-32-2.html
BOC Sciences	1330261-47-6	https://isotope.bocsci.com/product/sertaconazole-d6-cas-1330261-47-6-351315.html
BOC Sciences	1795786-36-5	https://isotope.bocsci.com/product/r-sertaconazole-d6-cas-1795786-36-5-344349.html
ChemMol	30111698	http://www.chemmol.com/chemmol/30111698.html
ChemMol	49403826	http://www.chemmol.com/chemmol/49403826.html
ChemMol	99179422	http://www.chemmol.com/chemmol/99179422.html
Chemspace	CSSB00000053394	https://chem-space.com/CSSB00000053394
Clearsynth	CS-O-05528	https://www.clearsynth.com/en/CSO05528.html
Clearsynth	CS-T-42269	https://www.clearsynth.com/en/CST42269.html
Clearsynth	CS-T-42271	https://www.clearsynth.com/en/CST42271.html
Clearsynth	CS-T-61282	https://www.clearsynth.com/en/CST61282.html
Clearsynth	CS-T-85170	https://www.clearsynth.com/en/CST85170.html
eNovation Chemicals	D590703	https://www.enovationchem.com/ProductDetails.asp?ProductID=D590703
Finetech	FT-0631003	http://www.finetechnology-ind.com/prod/detail/pub/99592-32-2.html
Finetech	FT-0674559	http://www.finetechnology-ind.com/prod/detail/pub/1330261-47-6.html
Finetech	FT-0674560	http://www.finetechnology-ind.com/prod/detail/pub/583057-48-1.html
Finetech	FT-0674561	http://www.finetechnology-ind.com/prod/detail/pub/583057-51-6.html
Glentham Life Sciences	GP3771	http://www.glentham.com/products/product/GP3771/
Hairui	HR104664	http://www.hairuichem.com/en/product/99592-32-2.html
Hefei Hirisun Pharmatech Co., Ltd	HR010089	http://www.hirisunpharm.com/99592-32-2.html
iChemical	EBD2202153	http://www.ichemical.com/products/99592-32-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Molcore	MC583730	https://www.molcore.com/product/99592-32-2
MuseChem	R064932	https://www.musechem.com/product/R064932.html
OChem	10917	http://www.ocheminc.com/index.php?act=psearch&pid=92S322
Smolecule	S605543	https://www.smolecule.com/products/s605543
THE BioTek	bt-312023	https://www.thebiotek.com/product/others/bt-312023
Vesino Industrial Co Ltd	VA11743	http://www.vsnchem.com/goto/product/22073/
Vitas-M Laboratory	STL452922	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL452922&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink

PubMed

Title	Date	PubMed
Comparative study of antifungal activity of sertaconazole, terbinafine, and bifonazole against clinical isolates of Candida spp., Cryptococcus neoformans and dermatophytes.	1997-12-13	9395851
Antifungal activity of sertaconazole in vitro against clinical isolates of Candida spp..	1996-03-01	8697886
In-vitro antifungal activity of sertaconazole, econazole, and bifonazole against Candida spp.	1995-10	8591947
In vitro comparative study of the fungistatic and fungicidal activity of sertaconazole and other antifungals against Candida albicans.	1992-05	1627188
In vitro antifungal activity of sertaconazole.	1992-05	1627187
In vitro activity of sertaconazole.	1992-05	1627186

Patents

Sample Use Guides

In Vivo Use Guide

Cream should be applied to the affected and immediate surrounding area(s) twice daily for 4 weeks.

Route of Administration: Topical

In Vitro Use Guide

MIC for Candida parapsilosis (0.26 mg/l) demonstrated a higher activity of sertaconazole against this species, in contrast to Candida tropicalis (MIC 1.49 mg/l). Against dermatophytes, MIC for sertaconazole was MIC 0.41 mg/l and against Cryptococcus neoformans yeasts - arithmetic mean MIC 1.24 mg/l.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:00:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:30 GMT 2025`
Record UNII	1DV05410M5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DERMOFIX

Preferred Name

English

SERTACONAZOLE NITRATE

Common Name

English

SERTACONAZOLE NITRATE [MART.]

Common Name

English

DERMOVIT

Brand Name

English

SERTACONAZOLE NITRATE [ORANGE BOOK]

Common Name

English

SERTACONAZOLE NITRATE [EP MONOGRAPH]

Common Name

English

1H-IMIDAZOLE, 1-(2-((7-CHLOROBENZO(B)THIEN-3-YL)METHOXY)-2-(2,4-DICHLOROPHENYL)ETHYL)-, NITRATE (1:1)

Systematic Name

English

FI 7056

Code

English

ZALAIN

Brand Name

English

Sertaconazole nitrate [WHO-DD]

Common Name

English

1H-IMIDAZOLE, 1-(2-((7-CHLOROBENZO(B)THIEN-3-YL)METHOXY)-2-(2,4-DICHLOROPHENYL)ETHYL)-, MONONITRATE

Systematic Name

English

ERTACZO

Brand Name

English

SERTACONAZOLE MONONITRATE

Common Name

English

SERTACONAZOLE NITRATE [MI]

Common Name

English

FI-7056

Code

English

Code System Code Type Description

RXCUI

236601

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

RxNorm

FDA UNII

1DV05410M5

Created by admin on Mon Mar 31 18:00:31 GMT 2025 , Edited by admin on Mon Mar 31 18:00:31 GMT 2025

PRIMARY

DRUG BANK

DBSALT001382

Created by admin on Mon Mar 31 18:00:31 GMT 2025 , Edited by admin on Mon Mar 31 18:00:31 GMT 2025

PRIMARY

EPA CompTox

DTXSID2045529

Created by admin on Mon Mar 31 18:00:31 GMT 2025 , Edited by admin on Mon Mar 31 18:00:31 GMT 2025

PRIMARY

NCI_THESAURUS

C47716

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

PUBCHEM

200103

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

EVMPD

SUB04374MIG

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

DAILYMED

1DV05410M5

Created by admin on Mon Mar 31 18:00:31 GMT 2025 , Edited by admin on Mon Mar 31 18:00:31 GMT 2025

PRIMARY

MERCK INDEX

m9874

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

Merck Index

CAS

99592-39-9

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

CHEBI

83687

Created by admin on Mon Mar 31 18:00:31 GMT 2025 , Edited by admin on Mon Mar 31 18:00:31 GMT 2025

PRIMARY

SMS_ID

100000084931

Created by admin on Mon Mar 31 18:00:31 GMT 2025 , Edited by admin on Mon Mar 31 18:00:31 GMT 2025

PRIMARY

ChEMBL

CHEMBL1201196

Created by admin on Mon Mar 31 18:00:30 GMT 2025 , Edited by admin on Mon Mar 31 18:00:30 GMT 2025

PRIMARY

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IMPURITY -> PARENT

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Qualification:

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Amount:


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CHROMATOGRAPHIC PURITY (HPLC/UV)

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IMPURITY -> PARENT

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CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

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Amount:

Related Record Type Details


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SERTACONAZOLE

ACTIVE MOIETY

Details

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound