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Identification
Name Sertaconazole
Accession Number DB01153 (APRD00305)
Type small molecule
Groups approved
Description

Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete’s foot. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Sertaconazol [Spanish]
Sertaconazolum [Latin]
Salts Not Available
Brand names
Name Company
Ertaczo
Brand mixtures Not Available
Categories
  • Antifungal Agents
CAS number 99592-32-2
Weight Average: 437.77
Monoisotopic: 435.997066923
Chemical Formula C20H15Cl3N2OS
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Benzothiophenes
  • Phenethylamines
Substructures
  • Benzyl Alcohols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Benzothiophenes
  • Imidazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Cyanamides
  • Thiophenes
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.
Pharmacodynamics 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.
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
Toxicity Not Available
Affected organisms
  • Yeast and other fungi
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Ortho dermatologics
Packagers
Dosage forms
Form Route Strength
Cream Topical
Prices
Unit description Cost Unit
Ertaczo 2% Cream 30 gm Tube 89.28 USD tube
Ertaczo 2% cream 2.6 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 5135943 1994-05-31 2014-05-31
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 6.37e-03 g/l ALOGPS
logP 5.74 ALOGPS
logP 6.23 ChemAxon
logS -4.8 ALOGPS
pKa (strongest basic) 6.77 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 27.05 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 111.6 ChemAxon
polarizability 42.93 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 65863 Link_out
PubChem Substance 46507290 Link_out
ChemSpider 59273 Link_out
Therapeutic Targets Database DAP001270 Link_out
PharmGKB PA164748328 Link_out
RxList http://www.rxlist.com/cgi/generic/ertaczo.htm Link_out
Drugs.com http://www.drugs.com/cdi/sertaconazole.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Sertaconazole Link_out
ATC Codes
  • D01AC14
AHFS Codes Not Available
PDB Entries
FDA label show (895 KB)
MSDS Not Available
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Cytochrome P450 51

Pharmacological action: yes
Actions: inhibitor

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

Organism class: fungal
UniProt ID: P10613 Link_out
Gene: ERG11
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. Agut J, Palacin C, Sacristan A, Ortiz JA: Inhibition of ergosterol synthesis by sertaconazole in Candida albicans. Arzneimittelforschung. 1992 May;42(5A):718-20. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed
Enzymes

1. Cytochrome P450 51A1

Actions: inhibitor

Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol

UniProt ID: Q16850 Link_out
Gene: CYP51A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19