You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameKetoconazole
Accession NumberDB01026  (APRD00401)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. [PubChem]

Structure
Thumb
Synonyms
Extina
Ketoconazol
Ketoconazole
Ketoconazolum
Ketozole
Nizoral
Nizoral a-D
Xolegel
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Extinaaerosol, foam20 mg/gtopicalPrestium Pharma, Inc.2014-01-10Not applicableUs
Ketoconazoleshampoo20 mg/mLtopicalPatriot Pharmaceuticals, LLC2005-07-01Not applicableUs
Ketoderm Cream 2%cream2 %topicalTaropharma, A Division Of Taro Pharmaceuticals Inc.2002-05-23Not applicableCanada
Nizoralshampoo20 mg/mLtopicalA S Medication Solutions Llc1990-08-31Not applicableUs
Nizoralshampoo20 mg/mLtopicalJanssen Pharmaceuticals, Inc.1990-08-31Not applicableUs
Nizoraltablet200 mg/1oralJanssen Pharmaceuticals, Inc.1981-06-12Not applicableUs
Nizoral Cream 2%cream2 %topicalMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1988-12-312007-08-02Canada
Nizoral Oral Suspension 20mg/mlsuspension20 mgoralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1989-12-311998-02-06Canada
Nizoral Shp 2%shampoo2 %topicalJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1990-12-311997-08-12Canada
Nizoral Tablets 200mgtablet200 mgoralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1984-12-312003-02-06Canada
Nu-ketocon Tablets - 200mgtablet200 mgoralNu Pharm Inc1998-09-012012-09-04Canada
Teva-ketoconazoletablet200 mgoralTeva Canada Limited1999-06-30Not applicableCanada
Xolegelgel2 %topicalBarrier Therapeutics Canada Inc.Not applicableNot applicableCanada
Xolegelgel20 mg/gtopicalAqua Pharmaceuticals2006-07-28Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ketoconazoletablet200 mgoralApotex Inc1998-02-03Not applicableCanada
Ketoconazolecream20 mg/gtopicalRebel Distributors Corp2002-12-18Not applicableUs
Ketoconazolecream20 mg/gtopicalTeva Pharmaceuticals USA Inc2000-04-27Not applicableUs
Ketoconazolecream20 mg/gtopicalDIRECT RX2014-01-01Not applicableUs
Ketoconazolecream20 mg/gtopicalREMEDYREPACK INC.2013-05-06Not applicableUs
Ketoconazoleaerosol, foam2 g/100gtopicalPerrigo New York Inc2011-08-30Not applicableUs
Ketoconazoleshampoo, suspension20 mg/mLtopicalPreferred Pharmaceuticals, Inc.2012-01-30Not applicableUs
Ketoconazoletablet200 mg/1oralbryant ranch prepack1999-06-15Not applicableUs
Ketoconazoleshampoo, suspension20 mg/mLtopicalPerrigo New York Inc2010-01-19Not applicableUs
Ketoconazoletablet200 mg/1oralGolden State Medical Supply, Inc.2009-05-20Not applicableUs
Ketoconazolecream20 mg/1topicalREMEDYREPACK INC.2013-04-15Not applicableUs
Ketoconazoletablet200 mg/1oralPreferred Pharmaceuticals, Inc.2013-02-05Not applicableUs
Ketoconazoletablet200 mg/1oralSTAT Rx USA LLC2011-05-31Not applicableUs
Ketoconazolecream20 mg/gtopicalPreferred Pharmaceuticals, Inc.2014-02-28Not applicableUs
Ketoconazoleshampoo, suspension20.5 mg/mLtopicalSandoz Inc.2005-11-04Not applicableUs
Ketoconazoleshampoo, suspension20 mg/mLtopicalPhysicians Total Care, Inc.2006-07-24Not applicableUs
Ketoconazolecream20 mg/gtopicalREMEDYREPACK INC.2013-06-12Not applicableUs
Ketoconazoleshampoo, suspension20.5 mg/mLtopicalPreferred Pharmaceuticals, Inc.2014-06-16Not applicableUs
Ketoconazoletablet200 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-20Not applicableUs
Ketoconazolecream20 mg/gtopicalG&W Laboratories, Inc.2015-06-15Not applicableUs
Ketoconazoletablet200 mg/1oralPhysicians Total Care, Inc.2004-05-24Not applicableUs
Ketoconazoletablet200 mg/1oralREMEDYREPACK INC.2013-03-15Not applicableUs
Ketoconazolecream20 mg/gtopicalUnit Dose Services2004-04-28Not applicableUs
Ketoconazoletablet200 mg/1oralPreferred Pharmaceuticals, Inc.2011-05-31Not applicableUs
Ketoconazoletablet200 mg/1oralAidarex Pharmaceuticals LLC1999-06-15Not applicableUs
Ketoconazoletablet200 mg/1oralMylan Pharmaceuticals Inc.2000-02-23Not applicableUs
Ketoconazolecream20 mg/gtopicalPhysicians Total Care, Inc.2001-08-01Not applicableUs
Ketoconazoletablet200 mg/1oralTaro Pharmaceuticals U.S.A., Inc.1999-06-15Not applicableUs
Ketoconazoletablet200 mg/1oralRebel Distributors Corp1999-06-15Not applicableUs
Ketoconazoletablet200 mg/1oralKAISER FOUNDATION HOSPITALS2010-03-02Not applicableUs
Ketoconazoletablet200 mg/1oralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Ketoconazolecream20 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2002-12-18Not applicableUs
Ketoconazoletablet200 mg/1oralAvera Mc Kennan Hospital2015-11-05Not applicableUs
Ketoconazolecream20 mg/gtopicalDispensing Solutions, Inc.2002-12-18Not applicableUs
Ketoconazolecream20 mg/gtopicalRebel Distributors Corp2002-12-18Not applicableUs
Ketoconazolecream20 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-04-28Not applicableUs
Ketoconazoleshampoo, suspension20 mg/mLtopicalAidarex Pharmaceuticals LLC2010-01-19Not applicableUs
Ketoconazoletablet200 mg/1oralLake Erie Medical DBA Quality Care Products LLC1999-06-15Not applicableUs
Ketoconazoletablet200 mg/1oralCarilion Materials Management1999-06-15Not applicableUs
Ketoconazolecream20 mg/gtopicalRebel Distributors Corp2002-12-18Not applicableUs
Ketoconazoletablet200 mg/1oralTeva Pharmaceuticals USA Inc1999-06-15Not applicableUs
Ketoconazolecream20 mg/gtopicalREMEDYREPACK INC.2013-06-04Not applicableUs
Ketoconazoletablet200 mg/1oralREMEDYREPACK INC.2011-07-14Not applicableUs
Ketoconazolecream20 mg/gtopicalPreferred Pharmaceuticals, Inc.2012-01-30Not applicableUs
Ketoconazoletablet200 mg/1oralAmerican Health Packaging2012-01-20Not applicableUs
KetodankitMedimetriks Pharmaceuticals, Inc.2012-06-15Not applicableUs
Ketodanaerosol, foam20 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2012-06-15Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nizoral - 2%shampoo2 %topicalJohnson & Johnson Inc1990-12-30Not applicableCanada
Nizoral A-Dshampoo10 mg/mLtopicalJohnson & Johnson Consumer Inc., Mc Neil Consumer Healthcare Division1999-04-01Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
FungarestJanssen-Cilag
FungoralJohnson & Johnson
KetodermHessel
KetoisdinIsdin
KetozoleRanbaxy
Nizoral CreamOrtho-McNeil
Nizoral ShampooOrtho-McNeil
OrifungalJanssen
Orifungal MJanssen
PanfungolEsteve
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIR9400W927I
CAS number65277-42-1
WeightAverage: 531.431
Monoisotopic: 530.148760818
Chemical FormulaC26H28Cl2N4O4
InChI KeyInChIKey=XMAYWYJOQHXEEK-UHFFFAOYSA-N
InChI
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3
IUPAC Name
1-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
SMILES
CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Substituted aniline
  • Dialkylarylamine
  • Phenol ether
  • 1,3-dichlorobenzene
  • Glycerol ether
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Alkyl aryl ether
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Acetamide
  • Tertiary carboxylic acid amide
  • Imidazole
  • Azole
  • Meta-dioxolane
  • Tertiary amine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.
PharmacodynamicsKetoconazole, like clotrimazole, fluconazole, itraconazole, and miconazole, is an imidazole antifungal agent.
Mechanism of actionKetoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone.
Related Articles
AbsorptionModerate
Volume of distributionNot Available
Protein binding99% (in vitro, plasma protein binding)
Metabolism

Hepatic

Route of eliminationNot Available
Half life2 hours
ClearanceNot Available
ToxicityHepatotoxicity, LD50=86 mg/kg (orally in rat)
Affected organisms
  • Fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.6704
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.7293
P-glycoprotein inhibitor IInhibitor0.8389
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterNon-inhibitor0.5644
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7409
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9386
Ames testNon AMES toxic0.7003
CarcinogenicityNon-carcinogens0.8836
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.4739 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9258
hERG inhibition (predictor II)Inhibitor0.8403
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Aerosol, foamtopical20 mg/g
Aerosol, foamtopical2 g/100g
Creamtopical20 mg/g
Creamtopical20 mg/1
Shampootopical20 mg/mL
Shampoo, suspensiontopical20 mg/mL
Shampoo, suspensiontopical20.5 mg/mL
Tabletoral200 mg/1
Kit
Creamtopical2 %
Shampootopical2 %
Shampootopical10 mg/mL
Suspensionoral20 mg
Tabletoral200 mg
Geltopical2 %
Geltopical20 mg/g
Prices
Unit descriptionCostUnit
Extina 2% Foam 100 gm Can375.44USD can
Extina 2% Foam 50 gm Can201.53USD can
Nizoral 2% Shampoo 120ml Bottle49.43USD bottle
Ketoconazole 2% Cream 60 gm Tube44.72USD tube
Ketoconazole 2% Cream 30 gm Tube29.43USD tube
Ketoconazole 2% Shampoo 120ml Bottle27.98USD bottle
Ketoconazole 2% Cream 15 gm Tube19.99USD tube
Ketoconazole powder15.0USD g
Nizoral 200 mg tablet4.75USD tablet
Extina 2% foam3.61USD g
Ketoconazole 200 mg tablet3.21USD tablet
Kuric 2% cream1.54USD g
Apo-Ketoconazole 200 mg Tablet1.24USD tablet
Novo-Ketoconazole 200 mg Tablet1.24USD tablet
Nu-Ketocon 200 mg Tablet1.24USD tablet
Nizoral 2% cream1.22USD g
Ketoconazole 2% cream1.1USD g
Ketoderm 2 % Cream0.35USD g
Ketoconazole 2% shampoo0.23USD ml
Nizoral a-d 1% shampoo0.07USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5456851 No1994-04-072014-04-07Us
US7179475 No1998-12-042018-12-04Us
US7553835 No1998-10-192018-10-19Us
US8026238 No1998-10-192018-10-19Us
US8232276 No2000-11-242020-11-24Us
US8735393 No1998-12-042018-12-04Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point146U.S. Patent 4,144,346.
water solubility0.0866 mg/LNot Available
logP4.35SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.00931 mg/mLALOGPS
logP4.3ALOGPS
logP4.19ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.06 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity138.07 m3·mol-1ChemAxon
Polarizability54.83 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 4,144,346.

General References
  1. Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. [PubMed:10933341 ]
  2. Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. [PubMed:10451809 ]
  3. Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. [PubMed:15737124 ]
  4. Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. [PubMed:12476017 ]
External Links
ATC CodesD01AC08G01AF11J02AB02
AHFS Codes
  • 08:14.08
  • 84:04.08.08
PDB EntriesNot Available
FDA labelDownload (222 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Ketoconazole.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Ketoconazole.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Ketoconazole.
AliskirenThe serum concentration of Aliskiren can be increased when it is combined with Ketoconazole.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Ketoconazole.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Ketoconazole.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Ketoconazole.
Aluminum hydroxideThe serum concentration of Ketoconazole can be decreased when it is combined with Aluminum hydroxide.
AmlodipineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Amlodipine.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Ketoconazole.
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Ketoconazole.
AmrinoneThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Amrinone.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Ketoconazole.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Ketoconazole.
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Ketoconazole resulting in a loss in efficacy.
AstemizoleKetoconazole may increase the QTc-prolonging activities of Astemizole.
AtorvastatinThe risk or severity of adverse effects can be increased when Atorvastatin is combined with Ketoconazole.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Ketoconazole.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Ketoconazole.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Ketoconazole.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Ketoconazole.
BepridilThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Bepridil.
BexaroteneThe serum concentration of Ketoconazole can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Ketoconazole.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Ketoconazole.
BosentanThe serum concentration of Ketoconazole can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Ketoconazole.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Ketoconazole.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Ketoconazole.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Ketoconazole.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Ketoconazole.
BuspironeThe metabolism of Buspirone can be decreased when combined with Ketoconazole.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Ketoconazole.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Ketoconazole.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Ketoconazole.
Calcium carbonateThe serum concentration of Ketoconazole can be decreased when it is combined with Calcium carbonate.
CapromabKetoconazole may decrease effectiveness of Capromab as a diagnostic agent.
CarbocisteineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Carbocisteine.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Ketoconazole.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Ketoconazole.
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Ketoconazole.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Ketoconazole.
CimetidineThe serum concentration of Ketoconazole can be decreased when it is combined with Cimetidine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Ketoconazole.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Ketoconazole.
ClopidogrelThe serum concentration of the active metabolites of Clopidogrel can be reduced when Clopidogrel is used in combination with Ketoconazole resulting in a loss in efficacy.
CobicistatThe serum concentration of Cobicistat can be increased when it is combined with Ketoconazole.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Ketoconazole.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Ketoconazole.
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Ketoconazole.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Ketoconazole.
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Ketoconazole.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be increased when it is combined with Ketoconazole.
DabrafenibThe serum concentration of Ketoconazole can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Ketoconazole.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Ketoconazole.
DarunavirThe serum concentration of Ketoconazole can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Ketoconazole.
DeferasiroxThe serum concentration of Ketoconazole can be decreased when it is combined with Deferasirox.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Ketoconazole.
DidanosineDidanosine can cause a decrease in the absorption of Ketoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Ketoconazole.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Ketoconazole.
DiltiazemThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Diltiazem.
DisopyramideThe serum concentration of Disopyramide can be increased when it is combined with Ketoconazole.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Ketoconazole.
DofetilideThe metabolism of Dofetilide can be decreased when combined with Ketoconazole.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Ketoconazole.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Ketoconazole.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Ketoconazole.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Ketoconazole.
DrospirenoneThe serum concentration of Drospirenone can be increased when it is combined with Ketoconazole.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Ketoconazole.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Ketoconazole.
EfavirenzThe serum concentration of Ketoconazole can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Ketoconazole.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Ketoconazole.
ElvitegravirThe serum concentration of Elvitegravir can be increased when it is combined with Ketoconazole.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Ketoconazole.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Ketoconazole.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Ketoconazole.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Ketoconazole.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Ketoconazole.
EsomeprazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Esomeprazole.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Ketoconazole.
EthanolThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Ethanol.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Ketoconazole.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Ketoconazole.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Ketoconazole.
FamotidineThe serum concentration of Ketoconazole can be decreased when it is combined with Famotidine.
FelodipineThe serum concentration of Felodipine can be increased when it is combined with Ketoconazole.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Ketoconazole.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Ketoconazole.
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Ketoconazole.
FimasartanThe serum concentration of Fimasartan can be increased when it is combined with Ketoconazole.
FingolimodThe serum concentration of the active metabolites of Fingolimod can be increased when Fingolimod is used in combination with Ketoconazole.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Ketoconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Ketoconazole.
FlunarizineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Flunarizine.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Ketoconazole.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Ketoconazole.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Ketoconazole.
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Ketoconazole.
FosphenytoinThe serum concentration of Ketoconazole can be decreased when it is combined with Fosphenytoin.
GabapentinThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Gabapentin.
GoserelinKetoconazole may increase the QTc-prolonging activities of Goserelin.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Ketoconazole.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Ketoconazole.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Ketoconazole.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Ketoconazole.
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Ketoconazole.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Ketoconazole resulting in a loss in efficacy.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Ketoconazole.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Ketoconazole.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Ketoconazole.
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Ketoconazole.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Ketoconazole.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Ketoconazole.
IsoniazidThe serum concentration of Ketoconazole can be decreased when it is combined with Isoniazid.
IsradipineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Isradipine.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Ketoconazole.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Ketoconazole.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Ketoconazole.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Ketoconazole.
LamotrigineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Lamotrigine.
LansoprazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Lansoprazole.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Ketoconazole.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Ketoconazole.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Ketoconazole.
LeuprolideKetoconazole may increase the QTc-prolonging activities of Leuprolide.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Ketoconazole.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Ketoconazole.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Ketoconazole.
LopinavirThe serum concentration of Lopinavir can be increased when it is combined with Ketoconazole.
LosartanThe metabolism of Losartan can be decreased when combined with Ketoconazole.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Ketoconazole.
LumacaftorThe serum concentration of Ketoconazole can be decreased when it is combined with Lumacaftor.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Ketoconazole.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Ketoconazole.
Magnesium hydroxideThe serum concentration of Ketoconazole can be decreased when it is combined with Magnesium hydroxide.
Magnesium oxideThe serum concentration of Ketoconazole can be decreased when it is combined with Magnesium oxide.
Magnesium SulfateThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Magnesium Sulfate.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Ketoconazole.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Ketoconazole.
MethadoneThe serum concentration of Methadone can be increased when it is combined with Ketoconazole.
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with Ketoconazole.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Ketoconazole.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Ketoconazole.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Ketoconazole.
MifepristoneThe serum concentration of Mifepristone can be increased when it is combined with Ketoconazole.
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Ketoconazole.
MitotaneThe serum concentration of Ketoconazole can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Ketoconazole.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Ketoconazole.
NevirapineThe serum concentration of Ketoconazole can be decreased when it is combined with Nevirapine.
NicardipineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Nicardipine.
NicotineThe metabolism of Nicotine can be decreased when combined with Ketoconazole.
NifedipineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Nifedipine.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Ketoconazole.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Ketoconazole.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Ketoconazole.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Ketoconazole.
NitrendipineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Nitrendipine.
NizatidineThe serum concentration of Ketoconazole can be decreased when it is combined with Nizatidine.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Ketoconazole.
OmeprazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Omeprazole.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Ketoconazole.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Ketoconazole.
OxycodoneThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Oxycodone.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Ketoconazole.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Ketoconazole.
PantoprazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Pantoprazole.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Ketoconazole.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Ketoconazole.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Ketoconazole.
PerhexilineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Perhexiline.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Ketoconazole.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Ketoconazole.
PimozideKetoconazole may increase the arrhythmogenic activities of Pimozide.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Ketoconazole.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Ketoconazole.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Ketoconazole resulting in a loss in efficacy.
PraziquantelThe serum concentration of Praziquantel can be increased when it is combined with Ketoconazole.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Ketoconazole.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Ketoconazole.
PrenylamineThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Prenylamine.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Ketoconazole.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Ketoconazole.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Ketoconazole.
QuinidineThe metabolism of Quinidine can be decreased when combined with Ketoconazole.
RabeprazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Rabeprazole.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Ketoconazole.
RanitidineThe serum concentration of Ketoconazole can be decreased when it is combined with Ranitidine.
RanolazineThe metabolism of Ranolazine can be decreased when combined with Ketoconazole.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Ketoconazole.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Ketoconazole.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Ketoconazole.
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Ketoconazole.
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Ketoconazole.
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Ketoconazole.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Ketoconazole.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Ketoconazole.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Ketoconazole.
RisedronateThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Risedronate.
RitonavirThe serum concentration of Ketoconazole can be increased when it is combined with Ritonavir.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Ketoconazole.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Ketoconazole.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Ketoconazole.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Ketoconazole.
SaquinavirThe serum concentration of Ketoconazole can be increased when it is combined with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Ketoconazole.
SildenafilThe metabolism of Sildenafil can be decreased when combined with Ketoconazole.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Ketoconazole.
SiltuximabThe serum concentration of Ketoconazole can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Ketoconazole.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Ketoconazole.
SirolimusThe serum concentration of Sirolimus can be increased when it is combined with Ketoconazole.
Sodium bicarbonateThe serum concentration of Ketoconazole can be decreased when it is combined with Sodium bicarbonate.
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Ketoconazole.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Ketoconazole.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Ketoconazole.
St. John's WortThe serum concentration of Ketoconazole can be decreased when it is combined with St. John's Wort.
SucralfateSucralfate can cause a decrease in the absorption of Ketoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
SunitinibThe metabolism of Sunitinib can be decreased when combined with Ketoconazole.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Ketoconazole.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Ketoconazole.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Ketoconazole.
TamoxifenThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ketoconazole resulting in a loss in efficacy.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Ketoconazole.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Ketoconazole.
TegafurThe serum concentration of the active metabolites of Tegafur can be reduced when Tegafur is used in combination with Ketoconazole resulting in a loss in efficacy.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Ketoconazole.
TelithromycinThe serum concentration of Telithromycin can be increased when it is combined with Ketoconazole.
TemsirolimusThe serum concentration of the active metabolites of Temsirolimus can be increased when Temsirolimus is used in combination with Ketoconazole.
TerfenadineKetoconazole may increase the QTc-prolonging activities of Terfenadine.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Ketoconazole.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Ketoconazole resulting in a loss in efficacy.
TipranavirThe serum concentration of Ketoconazole can be increased when it is combined with Tipranavir.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Ketoconazole.
TocilizumabThe serum concentration of Ketoconazole can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Ketoconazole.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Ketoconazole.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Ketoconazole.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Ketoconazole.
ToremifeneThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Ketoconazole.
TramadolThe therapeutic efficacy of Tramadol can be decreased when used in combination with Ketoconazole.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Ketoconazole.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Ketoconazole.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Ketoconazole.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Ketoconazole.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Ketoconazole.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Ketoconazole.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Ketoconazole.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Ketoconazole.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Ketoconazole.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Ketoconazole.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Ketoconazole.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Ketoconazole.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Ketoconazole.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Ketoconazole.
Food Interactions
  • Avoid alcohol.
  • Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Take with food.

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 ]
  7. Borgers M, Degreef H, Cauwenbergh G: Fungal infections of the skin: infection process and antimycotic therapy. Curr Drug Targets. 2005 Dec;6(8):849-62. [PubMed:16375669 ]
  8. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Eil C: Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70. [PubMed:1526623 ]
3. 17-hydroxylase 
Kind
Protein
Organism
Human
Pharmacological action
unknown
References
  1. Trachtenberg J, Zadra J: Steroid synthesis inhibition by ketoconazole: sites of action. Clin Invest Med. 1988 Feb;11(1):1-5. [PubMed:2966691 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Steroid hydroxylase activity
Specific Function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
CYP21A2
Uniprot ID:
P08686
Molecular Weight:
55886.805 Da
References
  1. Trachtenberg J, Zadra J: Steroid synthesis inhibition by ketoconazole: sites of action. Clin Invest Med. 1988 Feb;11(1):1-5. [PubMed:2966691 ]
5. 11-hydroxylase
Kind
Protein
Organism
Human
Pharmacological action
unknown
References
  1. Trachtenberg J, Zadra J: Steroid synthesis inhibition by ketoconazole: sites of action. Clin Invest Med. 1988 Feb;11(1):1-5. [PubMed:2966691 ]
  2. Loose DS, Kan PB, Hirst MA, Marcus RA, Feldman D: Ketoconazole blocks adrenal steroidogenesis by inhibiting cytochrome P450-dependent enzymes. J Clin Invest. 1983 May;71(5):1495-9. [PubMed:6304148 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Weber MM, Will A, Adelmann B, Engelhardt D: Effect of ketoconazole on human ovarian C17,20-desmolase and aromatase. J Steroid Biochem Mol Biol. 1991 Feb;38(2):213-8. [PubMed:2004042 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [PubMed:15969931 ]
  2. Elsherbiny ME, El-Kadi AO, Brocks DR: The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Pharm Sci. 2008;11(1):147-59. [PubMed:18445370 ]
  3. 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 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 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:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 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:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 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 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 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 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 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 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
  2. 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:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 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
inhibitorinducer
General Function:
Vitamin d 24-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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Elsherbiny ME, El-Kadi AO, Brocks DR: The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Pharm Sci. 2008;11(1):147-59. [PubMed:18445370 ]
  2. 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:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular Weight:
60101.87 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 11-beta-monooxygenase activity
Specific Function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular Weight:
57572.44 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:
Oxygen binding
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 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:
Retinoic acid binding
Specific Function:
Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsible for generation of several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA and 18-OH-RA.
Gene Name:
CYP26A1
Uniprot ID:
O43174
Molecular Weight:
56198.11 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:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 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:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 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:
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 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular Weight:
146405.83 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Choo EF, Leake B, Wandel C, Imamura H, Wood AJ, Wilkinson GR, Kim RB: Pharmacological inhibition of P-glycoprotein transport enhances the distribution of HIV-1 protease inhibitors into brain and testes. Drug Metab Dispos. 2000 Jun;28(6):655-60. [PubMed:10820137 ]
  2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
  3. Wang EJ, Lew K, Casciano CN, Clement RP, Johnson WW: Interaction of common azole antifungals with P glycoprotein. Antimicrob Agents Chemother. 2002 Jan;46(1):160-5. [PubMed:11751127 ]
  4. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
  5. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
  6. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
  7. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]
  8. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. doi: 10.1208/s12248-009-9092-5. Epub 2009 Mar 25. [PubMed:19319690 ]
  9. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. [PubMed:9822896 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular Weight:
74144.105 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on July 01, 2016 01:51