Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameSertaconazole
Accession NumberDB01153  (APRD00305)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
SertaconazolSpanishNot Available
SertaconazolumLatinNot Available
SaltsNot Available
Brand names
NameCompany
ErtaczoNot Available
Brand mixturesNot Available
Categories
CAS number99592-32-2
WeightAverage: 437.77
Monoisotopic: 435.997066923
Chemical FormulaC20H15Cl3N2OS
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzothiophenes
SubclassNot Available
Direct parentBenzothiophenes
Alternative parentsBenzylethers; Dichlorobenzenes; Aryl Chlorides; N-substituted Imidazoles; Thiophenes; Dialkyl Ethers; Polyamines; Organochlorides
Substituents1,3-dichlorobenzene; chlorobenzene; aryl halide; benzene; n-substituted imidazole; aryl chloride; thiophene; azole; imidazole; polyamine; ether; dialkyl ether; organochloride; amine; organonitrogen compound; organohalogen
Classification descriptionThis compound belongs to the benzothiophenes. These are organic compounds containing a benzene fused to a thiepine ring (a five-member ring with six carbon atoms and one sulfur atom).
Pharmacology
IndicationFor 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.
PharmacodynamicsSertaconazole 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 actionSertaconazole 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.
AbsorptionBioavailability is negligible.
Volume of distributionNot Available
Protein binding>99% to plasma
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Yeast and other fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Inhibitor 0.9103
CYP450 2D6 substrate Inhibitor 0.8931
CYP450 2C19 substrate Inhibitor 0.9474
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Ortho dermatologics
Packagers
Dosage forms
FormRouteStrength
CreamTopical
Prices
Unit descriptionCostUnit
Ertaczo 2% Cream 30 gm Tube89.28USDtube
Ertaczo 2% cream2.6USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States51359431994-05-312014-05-31
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubilityPractically insolubleNot Available
logP6.2Not Available
Predicted Properties
PropertyValueSource
water solubility6.37e-03 g/lALOGPS
logP5.74ALOGPS
logP6.23ChemAxon
logS-4.8ALOGPS
pKa (strongest basic)6.77ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area27.05ChemAxon
rotatable bond count6ChemAxon
refractivity111.6ChemAxon
polarizability42.93ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound65863
PubChem Substance46507290
ChemSpider59273
Therapeutic Targets DatabaseDAP001270
PharmGKBPA164748328
RxListhttp://www.rxlist.com/cgi/generic/ertaczo.htm
Drugs.comhttp://www.drugs.com/cdi/sertaconazole.html
WikipediaSertaconazole
ATC CodesD01AC14
AHFS CodesNot Available
PDB Entries
FDA labelshow(895 KB)
MSDSNot Available
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

1. Lanosterol 14-alpha demethylase

Kind: protein

Organism: Yeast

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Lanosterol 14-alpha demethylase P10613 Details

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

1. Lanosterol 14-alpha demethylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Lanosterol 14-alpha demethylase Q16850 Details

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 September 16, 2013 17:13