Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H15Cl3N2OS.HNO3 |
| Molecular Weight | 500.783 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.ClC1=CC(Cl)=C(C=C1)[C@H](CN2C=CN=C2)OCC3=CSC4=C3C=CC=C4Cl
InChI
InChIKey=HAAITRDZHUANGT-FYZYNONXSA-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)/t19-;/m0./s1
DescriptionCurator'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
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 |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | ERTACZO Approved UseERTACZO® (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 Date2003 |
Cmax
| 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 |
T1/2
| 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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
SERTACONAZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro activity of sertaconazole. | 1992 May |
|
| In-vitro antifungal activity of sertaconazole, econazole, and bifonazole against Candida spp. | 1995 Oct |
|
| Antifungal activity of sertaconazole in vitro against clinical isolates of Candida spp. | 1996 Mar-Apr |
|
| Comparative study of antifungal activity of sertaconazole, terbinafine, and bifonazole against clinical isolates of Candida spp., Cryptococcus neoformans and dermatophytes. | 1997 Nov-Dec |
Sample Use Guides
Cream should be applied to the affected and immediate surrounding area(s) twice daily for 4 weeks.
Route of Administration:
Topical
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.
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SUBSTANCE RECORD
