Identification
- Summary
Sertaconazole is a topical antifungal agent used in the treatment of interdigital tinea pedis in immunocompetent patients.
- Brand Names
- Ertaczo
- Generic Name
- Sertaconazole
- DrugBank Accession Number
- DB01153
- Background
Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available in topical formulations for the treatment of skin infections such as athlete's foot.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Sertaconazole (DB01153)
- Weight
- Average: 437.77
Monoisotopic: 435.997066923 - Chemical Formula
- C20H15Cl3N2OS
- Synonyms
- Sertaconazol
- Sertaconazole
- Sertaconazolum
- External IDs
- FI-7045
Pharmacology
- Indication
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.
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- Contraindications & Blackbox Warnings
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Sertaconazole is an imidazole/triazole type antifungal agent. Sertaconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent loss of normal sterols correlates with the accumulation of 14 α-methyl sterols in fungi and may be partly responsible for the fungistatic activity of fluconazole. Mammalian cell demethylation is much less sensitive to fluconazole inhibition. Sertaconazole exhibits in vitro activity against Cryptococcus neoformans and Candida spp. Fungistatic activity has also been demonstrated in normal and immunocompromised animal models for systemic and intracranial fungal infections due to Cryptococcus neoformans and for systemic infections due to Candida albicans.
- Mechanism of action
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. Sertaconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Target Actions Organism ACytochrome P450 51 inhibitorYeast - Absorption
Bioavailability is negligible.
- Volume of distribution
Not Available
- Protein binding
>99% to plasma
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.No interactions found.
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sertaconazole nitrate 1DV05410M5 99592-39-9 HAAITRDZHUANGT-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ertaczo Cream 20 mg/1g Topical Ortho-McNeil Janssen Pharmaceuticals, Inc 2011-10-17 2013-10-26 US 
Ertaczo Cream 20 mg/1g Topical Bausch Health US, LLC 2003-12-10 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ertaczo Cream 20 mg/1g Topical Rebel Distributors 2003-12-10 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ZALAIN CREAM 2% Cream 2 % Topical DCH AURIGA SINGAPORE 1999-05-17 Not applicable Singapore 
ZALAIN VAGINAL SUPPOSITORY 300 mg Suppository 300 mg Vaginal DCH AURIGA SINGAPORE 2002-04-29 Not applicable Singapore
Categories
- ATC Codes
- G01AF19 — Sertaconazole
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiophenes
- Sub Class
- 1-benzothiophenes
- Direct Parent
- 1-benzothiophenes
- Alternative Parents
- Benzylethers / Dichlorobenzenes / N-substituted imidazoles / Aryl chlorides / Thiophenes / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 2 more
- Substituents
- 1,3-dichlorobenzene / 1-benzothiophene / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Benzylether / Chlorobenzene show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- imidazoles, 1-benzothiophenes, ether, dichlorobenzene (CHEBI:83682)
- Affected organisms
- Yeast and other fungi
Chemical Identifiers
- UNII
- 72W71I16EG
- CAS number
- 99592-32-2
- InChI Key
- JLGKQTAYUIMGRK-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
- SMILES
- ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl
References
- General References
- External Links
- Human Metabolome Database
- HMDB0015284
- PubChem Compound
- 65863
- PubChem Substance
- 46507290
- ChemSpider
- 59273
- BindingDB
- 50051842
- 36435
- ChEBI
- 83682
- ChEMBL
- CHEMBL1201196
- Therapeutic Targets Database
- DAP001270
- PharmGKB
- PA164748328
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sertaconazole
- FDA label
- Download (895 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Foot Fungus / Ringworm / Tinea Pedis 1 2 Completed Treatment Skin Alterations Associated With Atopic Dermatitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Cream Topical 20 mg/1g Cream Topical 2 % Cream Vaginal 2 g Cream Topical 20 mg/g Insert Vaginal 500 mg Insert Vaginal 300 mg Cream Topical Insert Vaginal Cream Topical 2 g Solution Topical 2 % Emulsion Topical 2 g Powder Topical 2 g Solution Topical 2 g Cream Topical 2 %w/w Tablet Vaginal 300 mg Suppository Vaginal 300 mg Insert Vaginal 0.3 g - Prices
Unit description Cost Unit Ertaczo 2% Cream 30 gm Tube 89.28USD tube Ertaczo 2% cream 2.6USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5135943 No 1992-08-04 2014-05-31 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Practically insoluble Not Available logP 6.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00637 mg/mL ALOGPS logP 5.74 ALOGPS logP 6.23 Chemaxon logS -4.8 ALOGPS pKa (Strongest Basic) 6.48 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 27.05 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 111.6 m3·mol-1 Chemaxon Polarizability 42.93 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9879 Blood Brain Barrier + 0.9837 Caco-2 permeable + 0.5575 P-glycoprotein substrate Substrate 0.5548 P-glycoprotein inhibitor I Non-inhibitor 0.6546 P-glycoprotein inhibitor II Inhibitor 0.91 Renal organic cation transporter Inhibitor 0.6041 CYP450 2C9 substrate Non-substrate 0.8023 CYP450 2D6 substrate Non-substrate 0.8745 CYP450 3A4 substrate Non-substrate 0.6578 CYP450 1A2 substrate Inhibitor 0.9447 CYP450 2C9 inhibitor Inhibitor 0.9103 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Inhibitor 0.9474 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9966 Ames test Non AMES toxic 0.7933 Carcinogenicity Non-carcinogens 0.8668 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.4642 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6979 hERG inhibition (predictor II) Inhibitor 0.842
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Agut J, Palacin C, Sacristan A, Ortiz JA: Inhibition of ergosterol synthesis by sertaconazole in Candida albicans. Arzneimittelforschung. 1992 May;42(5A):718-20. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Agut J, Palacin C, Salgado J, Casas E, Sacristan A, Ortiz JA: Direct membrane-damaging effect of sertaconazole on Candida albicans as a mechanism of its fungicidal activity. Arzneimittelforschung. 1992 May;42(5A):721-4. [Article]
- Croxtall JD, Plosker GL: Sertaconazole: a review of its use in the management of superficial mycoses in dermatology and gynaecology. Drugs. 2009;69(3):339-59. doi: 10.2165/00003495-200969030-00009. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:25