Identification

Name
Econazole
Accession Number
DB01127  (APRD00943)
Type
Small Molecule
Groups
Approved
Description

A broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. [PubChem]

Structure
Thumb
Synonyms
  • (+-)-Econazole
  • 1-(2,4-Dichloro-beta-((P-chlorobenzyl)oxy)phenethyl)imidazole
  • Econazole
  • Econazole Nitrate
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Econazole Nitrate CreamCream10 mg/gTopicalAlvogen, Inc.2017-02-28Not applicableUs
Econazole Nitrate Topical Foam, 1%Aerosol, foam10 mg/gTopicalXiromed Llc2016-12-092017-05-12Us
Ecostatin Cream 1%Cream1 %TopicalBristol Myers Squibb1982-12-312006-09-05Canada
Ecostatin Vaginal Ovule 150mgSuppository150 mgVaginalBristol Myers Squibb1979-12-312007-05-30Canada
EcozaAerosol, foam10 mg/gTopicalExeltis Usa Dermatology, Llc2013-10-25Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Econazole NitrateCream10 mg/gTopicalPreferreed Pharmaceuticals Inc.2012-03-29Not applicableUs
Econazole NitrateCream10 mg/gTopicalAidarex Pharmaceuticals LLC2002-11-26Not applicableUs
Econazole NitrateCream10 mg/gTopicalPhysicians Total Care, Inc.2004-05-19Not applicableUs
Econazole NitrateCream10 mg/gTopicalA S Medication Solutions2006-08-082017-06-20Us
Econazole NitrateCream10 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2002-11-26Not applicableUs
Econazole NitrateCream10 mg/gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2002-11-26Not applicableUs
Econazole NitrateCream10 mg/gTopicalTeligent Pharma, Inc.2013-08-01Not applicableUs
Econazole NitrateCream10 mg/gTopicalPerrigo New York Inc.2006-08-08Not applicableUs
Econazole NitrateCream10 mg/1TopicalRemedy Repack2013-04-152017-02-15Us
Econazole NitrateCream10 mg/gTopicalRebel Distributors2004-06-23Not applicableUs
International/Other Brands
Ecostatin (Bristol-Myers Squibb) / Gyno-Pevaryl (Janssen) / Ifenec (Italfarmaco) / Palavale (Otsuka Pharmaceutical) / Pevaryl (Janssen) / Spectazole (Healthcare)
Categories
UNII
6Z1Y2V4A7M
CAS number
27220-47-9
Weight
Average: 381.684
Monoisotopic: 380.024996233
Chemical Formula
C18H15Cl3N2O
InChI Key
LEZWWPYKPKIXLL-UHFFFAOYSA-N
InChI
InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2
IUPAC Name
1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
SMILES
ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

Pharmacology

Indication

For topical application in the treatment of tinea pedis, tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Microsporum canis, Microsporum audouini, Microsporum gypseum, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis, and in the treatment of tinea versicolor.

Structured Indications
Pharmacodynamics

Econazole is an antifungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). Econazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.

Mechanism of action

Econazole 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. Econazole 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
ALanosterol 14-alpha demethylase
antagonist
Yeast
UNuclear receptor subfamily 1 group I member 2
partial agonist
Human
Absorption

After topical application to the skin of normal subjects, systemic absorption of econazole nitrate is extremely low. Although most of the applied drug remains on the skin surface, drug concentrations were found in the stratum corneum which, by far, exceeded the minimum inhibitory concentration for dermatophytes.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Overdosage of econazole in humans has not been reported to date. In mice, rats guinea pigs and dogs, the oral LD 50 values were found to be 462, 668, 272, and > 160 mg/kg, respectively.

Affected organisms
  • Yeast and other fungi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Econazole.Approved
AmlodipineThe risk or severity of adverse effects can be increased when Econazole is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Econazole.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Econazole is combined with Amrinone.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Econazole is combined with Atorvastatin.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Econazole is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Econazole is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Econazole is combined with Bepridil.Approved, Withdrawn
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Econazole.Approved, Investigational
BuspironeThe metabolism of Buspirone can be decreased when combined with Econazole.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Econazole.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Econazole.Approved
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Econazole is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Econazole is combined with Caroverine.Experimental
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Econazole.Withdrawn
CilnidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Econazole is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Econazole.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Clevidipine.Approved
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Econazole.Experimental
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Econazole.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Econazole.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Econazole is combined with Darodipine.Experimental
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Econazole.Approved
DidanosineDidanosine can cause a decrease in the absorption of Econazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Econazole.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Econazole.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Econazole.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Econazole.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Econazole is combined with Diltiazem.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Econazole.Experimental
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Econazole.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Econazole.Approved
DotarizineThe risk or severity of adverse effects can be increased when Econazole is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Efonidipine.Approved, Investigational
EperisoneThe risk or severity of adverse effects can be increased when Econazole is combined with Eperisone.Approved, Investigational
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Econazole.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Econazole.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Econazole.Withdrawn
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Econazole.Approved
FelodipineThe risk or severity of adverse effects can be increased when Econazole is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Econazole is combined with Fendiline.Withdrawn
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Econazole.Investigational
FlunarizineThe risk or severity of adverse effects can be increased when Econazole is combined with Flunarizine.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Econazole.Approved
FosphenytoinThe serum concentration of Econazole can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Econazole is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Econazole is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Econazole is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Econazole is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Lercanidipine.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Econazole is combined with Lidoflazine.Experimental
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Econazole.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Econazole.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Econazole.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Econazole.Illicit, Investigational, Withdrawn
Magnesium SulfateThe risk or severity of adverse effects can be increased when Econazole is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Econazole is combined with Manidipine.Approved, Investigational
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Econazole.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Econazole.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Econazole.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Econazole.Experimental
MibefradilThe risk or severity of adverse effects can be increased when Econazole is combined with Mibefradil.Investigational, Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Econazole is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Econazole is combined with Nicardipine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Econazole.Approved, Investigational
NifedipineThe risk or severity of adverse effects can be increased when Econazole is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Econazole is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Econazole is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Econazole is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Econazole is combined with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Econazole is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Econazole is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Econazole is combined with Nitrendipine.Approved, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Econazole is combined with Otilonium.Experimental, Investigational
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Econazole.Approved, Investigational, Vet Approved, Withdrawn
PerhexilineThe risk or severity of adverse effects can be increased when Econazole is combined with Perhexiline.Approved, Investigational
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Econazole.Approved, Investigational
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Econazole.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Econazole.Approved, Vet Approved
PimozideEconazole may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Econazole is combined with Pinaverium.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Econazole.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Econazole.Approved
PregabalinThe risk or severity of adverse effects can be increased when Econazole is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Econazole is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Econazole.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Econazole.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Econazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Econazole.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Econazole.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Econazole.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Econazole.Approved, Investigational
RisedronateThe risk or severity of adverse effects can be increased when Econazole is combined with Risedronate.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Econazole.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Econazole.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Econazole.Approved
SucralfateSucralfate can cause a decrease in the absorption of Econazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Econazole.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Econazole.Approved, Investigational
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Econazole.Experimental
TerodilineThe risk or severity of adverse effects can be increased when Econazole is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Econazole is combined with Tetrahydropalmatine.Investigational
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Econazole.Experimental
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Econazole is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Econazole is combined with Tranilast.Approved, Investigational
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Econazole.Approved, Experimental
VerapamilThe risk or severity of adverse effects can be increased when Econazole is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Econazole is combined with Vinpocetine.Investigational
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Econazole.Approved
XylometazolineThe risk or severity of adverse effects can be increased when Econazole is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Econazole is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Econazole.Approved
Food Interactions
Not Available

References

Synthesis Reference

Godefroi, E.F. and Heeres, J.; U.S. Patent 3,717,655; February 20,1973; assigned to Jansen Pharmaceutica NV, Belgium.

US3717655
General References
Not Available
External Links
Human Metabolome Database
HMDB15259
KEGG Drug
D03936
KEGG Compound
C08068
PubChem Compound
3198
PubChem Substance
46508881
ChemSpider
3086
BindingDB
31773
ChEBI
82873
ChEMBL
CHEMBL808
Therapeutic Targets Database
DAP001269
PharmGKB
PA164746010
IUPHAR
2446
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Econazole
ATC Codes
G01AF05 — EconazoleD01AC03 — EconazoleG01AF20 — Combinations of imidazole derivatives
FDA label
Download (203 KB)
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentInterdigital Tinea Pedis1
2CompletedTreatmentTinea Pedis1
2Unknown StatusTreatmentOnychomycosis1
3CompletedTreatmentTinea Pedis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
CreamTopical10 mg/g
CreamTopical10 mg/1
CreamTopical1 %
SuppositoryVaginal150 mg
Aerosol, foamTopical10 mg/g
Prices
Unit descriptionCostUnit
Econazole Nitrate 1% Cream 85 gm Tube73.63USD tube
Econazole Nitrate 1% Cream 30 gm Tube32.16USD tube
Econazole Nitrate 1% Cream 15 gm Tube19.32USD tube
Econazole nitrate powder2.5USD g
Spectazole 1% cream1.33USD g
Econazole nitrate 1% cream0.93USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5993830No1998-01-162018-01-16Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)162Godefroi, E.F. and Heeres, J.; U.S. Patent 3,717,655; February 20,1973; assigned to Jansen Pharmaceutica NV, Belgium.
logP5.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00148 mg/mLALOGPS
logP4.67ALOGPS
logP5.35ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.26 m3·mol-1ChemAxon
Polarizability37.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9735
Blood Brain Barrier+0.9823
Caco-2 permeable+0.6096
P-glycoprotein substrateNon-substrate0.545
P-glycoprotein inhibitor INon-inhibitor0.7958
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterInhibitor0.6806
CYP450 2C9 substrateNon-substrate0.8407
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7017
CYP450 1A2 substrateInhibitor0.9472
CYP450 2C9 inhibitorInhibitor0.939
CYP450 2D6 inhibitorInhibitor0.9413
CYP450 2C19 inhibitorInhibitor0.9591
CYP450 3A4 inhibitorInhibitor0.8861
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9961
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.853
BiodegradationNot ready biodegradable0.9933
Rat acute toxicity2.8478 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.8505
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0209000000-dd9a7887032ba981630f

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzylethers
Direct Parent
Benzylethers
Alternative Parents
Dichlorobenzenes / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Benzylether / 1,3-dichlorobenzene / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / N-substituted imidazole / Imidazole / Azole / Heteroaromatic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, ether, dichlorobenzene, monochlorobenzenes (CHEBI:82873)

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Antagonist
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. 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]
  2. Warrilow AG, Martel CM, Parker JE, Melo N, Lamb DC, Nes WD, Kelly DE, Kelly SL: Azole binding properties of Candida albicans sterol 14-alpha demethylase (CaCYP51). Antimicrob Agents Chemother. 2010 Oct;54(10):4235-45. doi: 10.1128/AAC.00587-10. Epub 2010 Jul 12. [PubMed:20625155]
  3. Strushkevich N, Usanov SA, Park HW: Structural basis of human CYP51 inhibition by antifungal azoles. J Mol Biol. 2010 Apr 9;397(4):1067-78. doi: 10.1016/j.jmb.2010.01.075. Epub 2010 Feb 10. [PubMed:20149798]
  4. Jackson CJ, Lamb DC, Kelly DE, Kelly SL: Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis. FEMS Microbiol Lett. 2000 Nov 15;192(2):159-62. [PubMed:11064188]
  5. Pietila MP, Vohra PK, Sanyal B, Wengenack NL, Raghavakaimal S, Thomas CF Jr: Cloning and characterization of CYP51 from Mycobacterium avium. Am J Respir Cell Mol Biol. 2006 Aug;35(2):236-42. Epub 2006 Mar 16. [PubMed:16543605]
  6. 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [PubMed:17998298]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 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]
Details
3. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:47