Sertaconazole

Identification

Name
Sertaconazole
Accession Number
DB01153
Description

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
Thumb
Weight
Average: 437.77
Monoisotopic: 435.997066923
Chemical Formula
C20H15Cl3N2OS
Synonyms
  • Sertaconazol
  • Sertaconazole
  • Sertaconazolum
External IDs
  • FI-7045

Pharmacology

Pharmacology
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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.

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ACytochrome P450 51
inhibitor
Yeast
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
Medicalerrors
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Toxicity
Not Available
Affected organisms
  • Yeast and other fungi
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

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Product Ingredients
IngredientUNIICASInChI Key
Sertaconazole nitrate1DV05410M599592-39-9HAAITRDZHUANGT-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ErtaczoCream20 mg/1gTopicalBausch Health US, LLC2003-12-10Not applicableUS flag
ErtaczoCream20 mg/1gTopicalOrtho-McNeil Janssen Pharmaceuticals, Inc2011-10-172013-10-26US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ErtaczoCream20 mg/1gTopicalRebel Distributors2003-12-10Not applicableUS flag

Categories

ATC Codes
G01AF19 — SertaconazoleG01AF20 — Combinations of imidazole derivativesD01AC14 — Sertaconazole
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)

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
  1. TITCK Product Information: Zalain (sertaconazole nitrate) vaginal tablet [Link]
  2. DailyMed: Ertaczo (sertaconazole) topical cream [Link]
  3. TITCK Product Information: Zalain (sertaconazole nitrate) topical solution [Link]
Human Metabolome Database
HMDB0015284
PubChem Compound
65863
PubChem Substance
46507290
ChemSpider
59273
BindingDB
50051842
RxNav
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
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentFoot Fungus / Ringworm / Tinea Pedis1
2CompletedTreatmentSkin Alterations Associated With Atopic Dermatitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
CreamTopical20 mg/1g
CreamVaginal
InsertVaginal
CreamTopical2 g
SolutionTopical2 %
EmulsionTopical
PowderTopical
SolutionTopical
SuppositoryVaginal
CreamTopical2 %w/w
TabletVaginal
CreamTopical
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)Region
US5135943No1992-08-042014-05-31US flag

Properties

State
Solid
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
  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]

Drug created on June 13, 2005 13:24 / Updated on September 16, 2020 21:09