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Details

Stereochemistry RACEMIC
Molecular Formula C20H15Cl3N2OS
Molecular Weight 437.77
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SERTACONAZOLE

SMILES

ClC1=CC(Cl)=C(C=C1)C(CN2C=CN=C2)OCC3=CSC4=C3C=CC=C4Cl

InChI

InChIKey=JLGKQTAYUIMGRK-UHFFFAOYSA-N
InChI=1S/C20H15Cl3N2OS/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/h1-8,11-12,19H,9-10H2

HIDE SMILES / InChI

Molecular Formula C20H15Cl3N2OS
Molecular Weight 437.77
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ERTACZO

Cmax

ValueDoseCo-administeredAnalytePopulation
1.79 ng/mL
300 mg single, vaginal
SERTACONAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
43.31 ng × h/mL
300 mg single, vaginal
SERTACONAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20.25 h
300 mg single, vaginal
SERTACONAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
SERTACONAZOLE plasma
Homo sapiens

Doses

PubMed

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
Record UNII
72W71I16EG
Record Status Validated (UNII)
Record Version