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Identification
NameSertaconazole
Accession NumberDB01153  (APRD00305)
TypeSmall Molecule
GroupsApproved
DescriptionSertaconazole 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
Demofix
Ertaczo
Sertaconazol
Sertaconazole
Sertaconazolum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErtaczoCream20 mg/gTopicalValeant Pharmaceuticals North America LLC2003-12-10Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ErtaczoCream20 mg/gTopicalRebel Distributors Corp.2003-12-10Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Sertaconazole nitrate
ThumbNot applicableDBSALT001382
Categories
UNII72W71I16EG
CAS number99592-32-2
WeightAverage: 437.77
Monoisotopic: 435.997066923
Chemical FormulaC20H15Cl3N2OS
InChI KeyJLGKQTAYUIMGRK-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
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Lanosterol 14-alpha demethylaseProteinyes
inhibitor
YeastP10613 details
Related Articles
AbsorptionBioavailability is negligible.
Volume of distributionNot Available
Protein binding>99% to plasma
MetabolismNot Available
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
Interactions
Drug Interactions
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Sertaconazole.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Azelnidipine.Approved
AzimilideThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Barnidipine.Approved
BenidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Benidipine.Approved
BepridilThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Sertaconazole.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Sertaconazole.Approved, Investigational
CaiThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Cai.Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Cinnarizine.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Sertaconazole.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Sertaconazole.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Sertaconazole.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Sertaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Sertaconazole.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Sertaconazole.Approved
DotarizineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Sertaconazole.Approved
FelodipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Sertaconazole can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Lacidipine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Lercanidipine.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Sertaconazole.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Manidipine.Approved
MibefradilThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Mibefradil.Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nilvadipine.Approved
NimesulideThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nimesulide.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Nitrendipine.Approved
PerhexilineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Sertaconazole.Approved, Vet Approved
PimozideSertaconazole may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Sertaconazole.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Sertaconazole.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Sertaconazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Sertaconazole.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Sertaconazole.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Sertaconazole.Approved
RisedronateThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Risedronate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Sertaconazole.Approved
SucralfateSucralfate can cause a decrease in the absorption of Sertaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Sertaconazole.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Sertaconazole.Approved, Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Sertaconazole.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD01AC14G01AF19
AHFS CodesNot Available
PDB Entries
FDA labelDownload (895 KB)
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9879
Blood Brain Barrier+0.9837
Caco-2 permeable+0.5575
P-glycoprotein substrateSubstrate0.5548
P-glycoprotein inhibitor INon-inhibitor0.6546
P-glycoprotein inhibitor IIInhibitor0.91
Renal organic cation transporterInhibitor0.6041
CYP450 2C9 substrateNon-substrate0.8023
CYP450 2D6 substrateNon-substrate0.8745
CYP450 3A4 substrateNon-substrate0.6578
CYP450 1A2 substrateInhibitor0.9447
CYP450 2C9 inhibitorInhibitor0.9103
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.9474
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9966
Ames testNon AMES toxic0.7933
CarcinogenicityNon-carcinogens0.8668
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.4642 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6979
hERG inhibition (predictor II)Inhibitor0.842
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical20 mg/g
Prices
Unit descriptionCostUnit
Ertaczo 2% Cream 30 gm Tube89.28USD tube
Ertaczo 2% cream2.6USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5135943 No1994-05-312014-05-31Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityPractically insolubleNot Available
logP6.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00637 mg/mLALOGPS
logP5.74ALOGPS
logP6.23ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity111.6 m3·mol-1ChemAxon
Polarizability42.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiophenes. These are organic compounds containing a benzene fused to a thiepine ring (a five-membered ring with six carbon atoms and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiophenes
Sub ClassNot Available
Direct ParentBenzothiophenes
Alternative Parents
Substituents
  • Benzylether
  • Benzothiophene
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Thiophene
  • Imidazole
  • Azole
  • Azacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

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
Molecular Weight:
60674.965 Da
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:17139284 ]
  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:17016423 ]
  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:1627190 ]
  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:10592235 ]
  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:1627191 ]
  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. doi: 10.2165/00003495-200969030-00009. [PubMed:19275277 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sterol 14-demethylase activity
Specific Function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular Weight:
56805.26 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23