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Identification
NameClotrimazole
Accession NumberDB00257  (APRD00244)
TypeSmall Molecule
GroupsApproved
Description

An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazoleNot AvailableNot Available
1-(alpha-(2-Chlorophenyl)benzhydryl)imidazoleNot AvailableNot Available
1-(O-Chloro-alpha,alpha-diphenylbenzyl)imidazoleNot AvailableNot Available
1-(o-Chloro-α,α-diphenylbenzyl)imidazoleNot AvailableNot Available
1-(o-Chlorotrityl)imidazoleNot AvailableNot Available
1-(α-(2-Chlorophenyl)benzhydryl)imidazoleNot AvailableNot Available
ClotrimazoleNot AvailableNot Available
Lotrimin (tn)Not AvailableNot Available
Mycelex (tn)Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Clotrimazolelozenge10 mgoral; topicalRoxane Laboratories, Inc2004-07-29Not AvailableUs
Clotrimazolelozenge10 mgoral; topicalRoxane Laboratories, Inc2004-07-29Not AvailableUs
Clotrimazolesolution10 mg/mLtopicalTeva Pharmaceuticals USA Inc1996-07-10Not AvailableUs
Clotrimazolecream10 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2008-09-02Not AvailableUs
Clotrimazolelozenge10 mgoralPaddock Laboratories, LLC2005-12-01Not AvailableUs
Clotrimazolecream10 mg/gtopicalSTAT Rx USA LLC1993-08-31Not AvailableUs
Clotrimazolesolution10 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.1996-07-29Not AvailableUs
Clotrimazolecream10 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1993-08-31Not AvailableUs
Clotrimazolelozenge10 mgoralREMEDYREPACK INC.2013-03-25Not AvailableUs
Clotrimazolelozenge10 mgoralPhysicians Total Care, Inc.2009-07-23Not AvailableUs
Clotrimazolelozenge10 mgoral; topicalCardinal Health2004-07-29Not AvailableUs
Clotrimazolecream10 mg/gtopicalGlenmark Generics Inc., USA2010-08-04Not AvailableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Good Sense Athletes Foot antifungalcream1 g/100gtopicalL Perrigo Company2006-04-09Not AvailableUs
Clotrimazole Athletes Footcream10 mg/gtopicalKAISER FOUNDATION HOSPITALS1993-08-31Not AvailableUs
Clotrimazolecream1 g/100gvaginalWalgreen Company1998-09-01Not AvailableUs
Walgreens Clotrimazolecream1 g/100gtopicalWalgreen Co2011-04-14Not AvailableUs
Walgreens Clotrimazole 3cream2 g/100gvaginalWalgreen Company2000-04-12Not AvailableUs
Walgreens Jock Itchcream10 mg/gtopicalWalgreen Company1993-08-31Not AvailableUs
Jock Itchcream1 g/100gtopicalWalgreen Company2014-06-15Not AvailableUs
Walgreens Clotrimazole Antifungalcream1 g/100gtopicalWalgreen Company2014-12-12Not AvailableUs
Clotrimazolecream1 g/100gvaginalActavis Mid Atlantic LLC2003-08-12Not AvailableUs
Major Clotrimazolecream10 mg/gtopicalMajor Pharmaceuticals2004-10-04Not AvailableUs
Gyne-lotrimin 3cream2 g/100gvaginalMSD Consumer Care, Inc.2002-01-01Not AvailableUs
Gyne-lotrimin 7cream1 g/100gvaginalMSD Consumer Care, Inc.2002-01-01Not AvailableUs
Lotrimincream10 mg/gtopicalMSD Consumer Care, Inc.2002-02-01Not AvailableUs
Lotrimin Antifungalcream10 mg/gtopicalMSD Consumer Care, Inc.2002-02-01Not AvailableUs
Lotrimincream10 mg/gtopicalMSD Consumer Care, Inc.2009-01-02Not AvailableUs
Dr Sheffield Athletes Footcream10 mg/gtopicalFaria Limited dba Sheffield Pharmaceuticals2004-10-04Not AvailableUs
Upandup Clotrimazolecream10 mg/gtopicalTarget Corporation1993-08-31Not AvailableUs
Clotrimazole 7cream1 g/100gvaginalRite Aid1996-11-22Not AvailableUs
Foot Care Clotrimazolecream10 mg/gtopicalRite Aid2010-03-12Not AvailableUs
Antifungal Creamcream10 mg/gtopicalRite Aid2011-04-15Not AvailableUs
Jock Itchcream1 g/100gtopicalRite Aid Corporation2005-08-07Not AvailableUs
Rite Aid antifungal ringwormcream1 g/100gtopicalRite Aid Corporation1995-06-01Not AvailableUs
Lucky Supersoft Athletes Footcream1 g/100gtopicalDelta Brands, Inc2015-01-31Not AvailableUs
Antifungalcream1 g/100gtopicalSafeway2008-11-20Not AvailableUs
Clotrimazolecream1 g/100gtopicalRebel Distributors Corp1995-06-01Not AvailableUs
Clotrimazolecream50 mg/gtopicalRebel Distributors Corp.1993-07-16Not AvailableUs
Good Neighbor Pharmacy Clotrimazole 3cream2 g/100gvaginalAmerisource Bergen2000-04-12Not AvailableUs
Good Neighbor Pharmacy Clotrimazolecream10 mg/gtopicalAmerisource Bergen1993-08-31Not AvailableUs
Terrasil Jock-itch Treatment MAXointment1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2014-05-12Not AvailableUs
Terrasil Ringworm Treatment MAXointment1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2014-05-12Not AvailableUs
Terrasil Tinea Treatment MAXointment1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2014-05-12Not AvailableUs
Terrasil Anti-fungal Treatment MAXointment1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2012-09-07Not AvailableUs
Terrasil Rapid-clear Anti-fungalkitAidance Skincare & Topical Solutions, LLC2014-04-18Not AvailableUs
Femmesilcream1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2014-11-30Not AvailableUs
Pedesil Maximum Strengthointment1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2012-09-07Not AvailableUs
Pedesilcream1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2012-09-07Not AvailableUs
Aspiera Anti-fungalointment1 g/100gtopicalAidance Skincare & Topical Solutions, LLC2012-05-31Not AvailableUs
Budpak Antifungal Clotrimazolecream.01 g/gtopicalBudpak Inc.2012-12-17Not AvailableUs
Jock Itch Antifungalcream420 mg/42gtopicalPersonal Care Products, Inc.2013-07-10Not AvailableUs
Athletes Foot Antifungal Antifungalcream350 mg/35gtopicalPersonal Care Products, Inc.2013-07-10Not AvailableUs
Kroger ATHLETES FOOTcream10 mg/gtopicalKroger Company1993-08-31Not AvailableUs
Kroger Jock Itchcream10 mg/gtopicalKroger Company1993-08-31Not AvailableUs
Topcare Clotrimazole 3cream2 g/100gvaginalTopco Associates LLC2000-04-12Not AvailableUs
Topcare Antifungalcream10 mg/gtopicalTopco Associates LLC1993-08-31Not AvailableUs
Shopko Athletes Footcream10 mg/gtopicalShopko Stores Operating Co., LLC1993-08-31Not AvailableUs
Clotrimazolecream10 mg/gtopicalCardinal Health1993-08-31Not AvailableUs
Leader Clotrimazole Anti-fungalcream1 g/100gtopicalCardinal Health2013-05-31Not AvailableUs
Heb Antifungalcream10 mg/gtopicalH E B1993-08-31Not AvailableUs
Equaline Clotrimazole Antifungalcream1 g/100gtopicalSupervalu Inc2011-09-29Not AvailableUs
Meijer Clotrimazole 3cream2 g/100gvaginalMeijer Distribution Inc2000-04-12Not AvailableUs
Meijer Athletes Footcream10 mg/gtopicalMeijer Distribution Inc1993-08-31Not AvailableUs
Meijer Clotrimazole Antifungalcream1 g/100gtopicalMEIJER, INC.2015-01-15Not AvailableUs
Publix athletic footcream10 mg/gtopicalPublix Super Markets Inc1993-08-31Not AvailableUs
Careone Clotrimazolecream10 mg/gtopicalAmerican Sales Company1993-08-31Not AvailableUs
Clotrimazolecream1 g/100gtopicalRebel Distributors Corp2011-06-03Not AvailableUs
Footlogixaerosol, spray1 mL/100mLtopicalKVG Group Inc2010-09-01Not AvailableUs
Footlogix Intensive Care diabetic formulaaerosol, foam1 g/100gtopicalKVG Group Inc2012-06-15Not AvailableUs
Gehwol Med Footpowder1 g/100gtopicalEduard Gerlach Gmb H2008-12-04Not AvailableUs
Gerlasan Handcream6 mg/mLtopicalEduard Gerlach Gmb H2008-12-04Not AvailableUs
Gehwol Nail Protection Penliquid10 mg/mLtopicalEduard Gerlach Gmb H2008-03-07Not AvailableUs
Clotrimazolecream1 g/100gtopicalPerrigo New York Inc2011-06-03Not AvailableUs
Aptrimazole 1.0% ANTIFUNGAL CREAMcream1 g/100gtopicalA P J Laboratories Limited2013-04-27Not AvailableUs
Clotrimazole Jock Itchcream10 mg/gtopicalWal Mart Stores, Inc.1993-08-31Not AvailableUs
Clotrimazole Athletes Footcream10 mg/gtopicalWal Mart Stores, Inc.1993-08-31Not AvailableUs
Sunmark Antifungalcream10 mg/gtopicalMc Kesson1993-08-31Not AvailableUs
Sunmark Clotrimazole 3cream2 g/100gvaginalMc Kesson2000-04-12Not AvailableUs
Clotrimazolecream10 mg/gtopicalMc Kesson1993-07-19Not AvailableUs
Smart Sense Athletes Foot antifungalcream1 g/100gtopicalKmart Corporation2010-11-19Not AvailableUs
Clotrimazolecream1 g/100gtopicalNeo Pharm Co., Ltd.2010-09-02Not AvailableUs
Atopalm Clotrimazole Antifungalcream1 g/100gtopicalNeo Pharm Co., Ltd.2011-03-16Not AvailableUs
Live Better Antifungalcream10 mg/gtopicalThe Great Atlantic & Pacific Tea Company1993-08-31Not AvailableUs
Clotrimazolecream1 g/100gtopicalTaro Pharmaceuticals U.S.A., Inc.1995-06-01Not AvailableUs
Clotrimazolecream1 g/100gvaginalTaro Pharmaceuticals U.S.A., Inc.1995-12-04Not AvailableUs
Clotrimazolesolution1 g/mLtopicalTaro Pharmaceuticals U.S.A., Inc.1996-05-01Not AvailableUs
Clotrimazolecream2 g/100gvaginalTaro Pharmaceuticals U.S.A., Inc.2000-04-12Not AvailableUs
Jideshenggel1 g/100gtopicalUPC Medical Supplies, Inc.2010-10-23Not AvailableUs
Jideshenggel1 g/100gtopicalNantong Jidesheng Biology Health Care Products Co., Ltd.2010-10-23Not AvailableUs
Clotrimazolecream10 mg/gtopicalLif Elabs, A Division Of Atico International Usa, Inc.2010-11-01Not AvailableUs
Fungicure Manicure Pedicureliquid10 mg/mLtopicalAlva Amco Pharmacal Companies, Inc.2002-07-15Not AvailableUs
Fungicure Pumpsprayliquid10 mg/mLtopicalAlva Amco Pharmacal Companies, Inc.2002-03-01Not AvailableUs
Fungicure Intensiveliquid10 mg/mLtopicalAlva Amco Pharmacal Companies, Inc.2008-06-05Not AvailableUs
Clotrimazolecream1 g/100gtopicalH.J. Harkins Company, Inc.1995-06-01Not AvailableUs
Clotrimazolecream1 g/100gtopicalGeritrex Corp2014-07-29Not AvailableUs
Dermatin Antifungalcream.01 g/gtopicalMelaleuca, Inc.2011-12-19Not AvailableUs
Clotrimazolecream10 mg/gtopicalPhysicians Total Care, Inc.2003-08-07Not AvailableUs
Clotrimazole Antifungalcream10 mg/gtopicalArmy and Air Force Exchange Service2006-02-03Not AvailableUs
Western Family Athletes Footcream10 mg/gtopicalWestern Family Foods Inc1993-08-31Not AvailableUs
Family Wellness Antifungalcream10 mg/gtopicalFamily Dollar2014-01-20Not AvailableUs
Family Wellness Antifungalcream1 g/100gtopicalFamily Dollar2012-04-01Not AvailableUs
Family Wellness Antifungalcream10 mg/gtopicalFamily Dollar2014-01-21Not AvailableUs
Theraplus Pluscream1 g/100gtopicalZhejiang Jingwei Pharmaceutical Co., Ltd.2013-03-01Not AvailableUs
Major Clotrimazolecream10 mg/gtopicalClinical Solutions Wholesale2004-10-04Not AvailableUs
Clotrimazolecream1 g/100gtopicalPromex, LLC2013-12-04Not AvailableUs
Cvs Pharmacy Clotrimazole 3cream2 g/100gvaginalCVS Pharmacy2000-04-12Not AvailableUs
Clotrimazole 1% Athletes Footcream10 mg/gtopicalCVS Pharmacy1993-08-31Not AvailableUs
Cvs Pharmacy ITCH RELIEF ANTIFUNGALcream10 mg/gtopicalCVS Pharmacy1993-08-31Not AvailableUs
Cvs Antifungal Ringwormcream1 g/100gtopicalCVS Pharmacy1995-06-01Not AvailableUs
Clotrimazolecream1 g/100gtopicalNavarro Discount Pharmacies, LLC2012-08-01Not AvailableUs
Clotrimazolecream1 g/100gtopicalTaro Pharmaceuticals, Inc.1995-06-01Not AvailableUs
Clotrimazolesolution1 g/mLtopicalTaro Pharmaceuticals, Inc.1996-05-01Not AvailableUs
Clotrimazolecream1 g/100gtopicalKinray Inc.2012-01-11Not AvailableUs
Clotrimazolecream1 g/100gvaginalChain Drug Marketing Association Inc.2014-10-15Not AvailableUs
Quality Choice Clotrimazolecream10 mg/gtopicalChain Drug Marketing Association2015-01-19Not AvailableUs
Clotrimazole Antifungalcream10 mg/gtopicalChain Drug Marketing Association Inc.2007-08-29Not AvailableUs
Best Choice Clotrimazolecream10 mg/gtopicalValu Merchandisers Company1993-08-31Not AvailableUs
Soundbody Clotrimazole Antifungalcream10 mg/gtopicalUNITED EXCHANGE CORP.2014-02-26Not AvailableUs
Family Care Clotrimazole Antifungalcream1 g/100gtopicalUNITED EXCHANGE CORP.2012-05-01Not AvailableUs
Anti-fungalcream10 mg/gtopicalMPM Medical, Inc.2002-10-14Not AvailableUs
Winco Antifungalcream10 mg/gtopicalWin Co Foods, Llc2015-02-10Not AvailableUs
Athlete S Foot Afaccream.01 g/gtopicalNatureplex, LLC2008-01-22Not AvailableUs
Pro-ex Anti Fungalcream.01 g/gtopicalNatureplex, LLC2008-01-22Not AvailableUs
Clotrimazolecream1 g/100gtopicalKareway Product, Inc.2011-08-11Not AvailableUs
Antifungal Clotrimazolecream10 mg/gtopicalPremier Value2003-09-11Not AvailableUs
Clotrimazolecream1 g/100gtopicalPremier Value2013-10-09Not AvailableUs
Clotrimazolecream10 mg/gtopicalPreferred Pharmaceuticals, Inc.2013-08-06Not AvailableUs
Clotrimazolecream1 g/100gvaginalPreferred Pharmaceuticals, Inc.2013-08-06Not AvailableUs
Clotrimazolecream1 g/100gvaginalPreferred Pharmaceuticals, Inc.2013-08-05Not AvailableUs
Clotrimazoil Antifungalsolution10 mg/mLtopicalPEDIFIX, INC.2013-06-19Not AvailableUs
Clotrimazoleliquid10 mg/mLtopicalPedifix2014-05-05Not AvailableUs
Makesensecream1 g/100gtopicalCherry Hill Sales Co2014-06-15Not AvailableUs
Our Family Athletes Footcream10 mg/gtopicalNash Finch Company1993-08-31Not AvailableUs
First Aid Research Antifungal .5ozcream10 mg/gtopicalFirst Aid Research Corp.2014-10-14Not AvailableUs
First Aid Research Antifungal Cream 1ozcream10 mg/gtopicalFirst Aid Research Corp.2014-10-14Not AvailableUs
Hua Tuo Xian Gaoointment1 mg/100gtopicalSHANGHAI SONGHUA PHARMACEUTICAL CO LTD2011-04-28Not AvailableUs
International Brands
NameCompany
CanestenBayer
CanifugDr. August Wolff
ClotrimadermTaro
EmpecidBayer
FemCareNot Available
FungicipCipla
Gyne-LotriminSchering-Plough
MycelexBayer
Myclo-DermNot Available
Myclo-GyneNot Available
Brand mixtures
Brand NameIngredients
Lotrisoneclotrimazole + betamethasone
SaltsNot Available
Categories
CAS number23593-75-1
WeightAverage: 344.837
Monoisotopic: 344.108026261
Chemical FormulaC22H17ClN2
InChI KeyVNFPBHJOKIVQEB-UHFFFAOYSA-N
InChI
InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
IUPAC Name
1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
SMILES
ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • N-substituted imidazole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the local treatment of oropharyngeal candidiasis and vaginal yeast infections, also used in fungal infections of the skin such as ringworm, athlete's foot, and jock itch.
PharmacodynamicsClotrimazole, an imidazole derivative with a broad spectrum of antimycotic activity, inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections. In studies in fungal cultures, the minimum fungicidal concentration of clotrimazole caused leakage of intracellular phosphorous compounds into the ambient medium with concomitant breakdown of cellular nucleic acids, and accelerated potassium etflux. Both of these events began rapidly and extensively after addition of the drug to the cultures. The primary action of clotrimazole is against dividing and growing organisms.
Mechanism of actionClotrimazole interacts with yeast 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.
AbsorptionPoorly and erratically absorbed orally, minimal vaginal or topical absorption.
Volume of distributionNot Available
Protein binding90%
Metabolism

Hepatic (metabolized to inactive metabolites)

Route of eliminationNot Available
Half life2 hours
ClearanceNot Available
ToxicitySymptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Affected organisms
  • Yeast and other fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9725
Blood Brain Barrier+0.9837
Caco-2 permeable+0.6858
P-glycoprotein substrateNon-substrate0.7185
P-glycoprotein inhibitor INon-inhibitor0.6612
P-glycoprotein inhibitor IINon-inhibitor0.7884
Renal organic cation transporterNon-inhibitor0.5854
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9149
CYP450 3A4 substrateNon-substrate0.6262
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 substrateInhibitor0.8948
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateInhibitor0.8994
CYP450 3A4 substrateInhibitor0.8478
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9799
Ames testNon AMES toxic0.7428
CarcinogenicityNon-carcinogens0.9018
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7194 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9659
hERG inhibition (predictor II)Inhibitor0.6779
Pharmacoeconomics
Manufacturers
  • Schering plough healthcare products inc
  • Bayer pharmaceuticals corp
  • Glenmark pharmaceuticals inc usa
  • Nycomed us inc
  • Taro pharmaceuticals usa inc
  • Actavis mid atlantic llc
  • Taro pharmaceuticals inc
  • Schering corp sub schering plough corp
  • Teva pharmaceuticals usa inc
  • Bayer healthcare pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Paddock laboratories inc
  • Roxane laboratories inc
Packagers
Dosage forms
FormRouteStrength
Aerosol, foamtopical1 g/100g
Aerosol, spraytopical1 mL/100mL
Creamtopical.01 g/g
Creamtopical1 g/100g
Creamtopical10 mg/g
Creamtopical350 mg/35g
Creamtopical420 mg/42g
Creamtopical50 mg/g
Creamtopical6 mg/mL
Creamvaginal1 g/100g
Creamvaginal2 g/100g
Geltopical1 g/100g
Kit
Liquidtopical10 mg/mL
Lozengeoral10 mg
Lozengeoral; topical10 mg
Ointmenttopical1 g/100g
Ointmenttopical1 mg/100g
Powdertopical1 g/100g
Solutiontopical1 g/mL
Solutiontopical10 mg/mL
Prices
Unit descriptionCostUnit
Clotrimazole 70 10 mg Troche Bottle117.04USD bottle
Clotrimazole 1% Cream 45 gm Tube49.99USD tube
Clotrimazole 1% Cream 30 gm Tube35.99USD tube
Clotrimazole 1% Solution 30ml Bottle24.99USD bottle
Clotrimazole 1% Cream 15 gm Tube17.99USD tube
Clotrimazole 1% Solution 10ml Bottle17.99USD bottle
Clotrimazole powder5.2USD g
Mycelex 10 mg troche1.85USD troche
Clotrimazole 10 mg troche1.61USD troche
Mycelex-7 100 mg vaginal tablet1.33USD tablet
Lotrimin 1% cream1.28USD g
Gyne-lotrimin insert1.03USD insert
Mycelex 1% cream0.9USD g
Clotrimazole insert0.86USD insert
Lotrimin ultra 1% cream0.68USD g
Clotrimazole 1% cream0.53USD g
Clotrimazole 3 2% cream0.5USD g
Ra clotrimazole 3 cream0.46USD g
Ra athlete's 1% foot cream0.37USD g
Desenex 1% cream0.33USD g
CVS Pharmacy clotrimazole 1% cream0.32USD g
Antifungal 1% cream0.27USD g
Sm antifungal 1% cream0.25USD g
Ra clotrimazole af cream0.24USD g
Clotrim 1% vaginal cream0.18USD g
Lotrimin af 2% spray powder0.05USD g
Lotrimin af 2% liquid spray0.04USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point154-156Buechel, K.H., et al; South African Patent 69/0039; January 3, 1969; assigned to Farben- Buechel, K.H., Regel, E. and Plempel, M.; US. Patent 3,660,577; May 2,1972; and U.S. fabriken Bayer AG, Germany. Patent 3,705,172; Dec. 5,1972; both assigned to Farbenfabriken Bayer A.G. (Germany).
water solubility29.84 mg/mLNot Available
logP6.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00147 mg/mLALOGPS
logP5.48ALOGPS
logP5.84ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.76 m3·mol-1ChemAxon
Polarizability36.25 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS/MSMS1D NMR2D NMR
References
Synthesis Reference

Buechel, K.H., et al; South African Patent 69/0039; January 3, 1969; assigned to Farben- Buechel, K.H., Regel, E. and Plempel, M.; US. Patent 3,660,577; May 2,1972; and U.S. fabriken Bayer AG, Germany.
Patent 3,705,172; Dec. 5,1972; both assigned to Farbenfabriken Bayer A.G. (Germany).

US3705172
General ReferenceNot Available
External Links
ATC CodesA01AB18D01AC01G01AF02
AHFS Codes
  • 84:04.08.08
PDB EntriesNot Available
FDA labelDownload (139 KB)
MSDSDownload (73.8 KB)
Interactions
Drug Interactions
Drug
AlvimopanDecreases levels by P-glycoprotein (MDR-1) efflux transporter. Can significantly increase systemic exposure to P-glycoprotein substrates.
BudesonideCYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of Budesonide (Systemic, Oral Inhalation). Consider reducing the oral budesonide dose when used together with a CYP3A4 inhibitor. This interaction is likely less severe with orally inhaled budesonide. Any patient receiving both budesonide and a moderate CYP3A4 inhibitor should be monitored closely for signs/symptoms of corticosteroid excess.
ColchicineCYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of colchicine. Reduce colchicine dose (for gout flares: to 1.2 mg x 1 dose, with next dose no sooner than 3 days later; for Familial Mediterranean Fever: to no more than 1.2 mg/day) when using in combination with a moderate CYP3A4 inhibitor such as erythromycin or verapamil. Increase monitoring for colchicine-related toxicity when using such combinations. Use extra caution in patients with impaired renal and/or hepatic function.
EverolimusCYP3A4 Inhibitors (Moderate)such as clotrimazole may increase the serum concentration of everolimus. The prescribing information for the Afinitor branded everolimus product lists indication-specific recommendations for managing this interaction.
FentanylCYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of fentanyl. Concurrent use of fentanyl with any CYP3A4 inhibitor may result in increased fentanyl concentrations and could increase or prolong adverse effects, including potentially fatal respiratory depression. Patients receiving fentanyl and any CYP3A4 inhibitor should be closely monitored for several days following initiation of the combination, and fentanyl dosage reductions should be made as appropriate.
HalofantrineCYP3A4 Inhibitors (Moderate) such as clotrmazole may increase the serum concentration of halofantrine. Extreme caution, with possibly increased monitoring of cardiac status (e.g., ECG), should be used with concurrent use of halofantrine with any moderate CYP3A4 inhibitor(s).
LurasidoneCYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of lurasidone. Limit adult lurasidone dose to 40 mg/day in patients receiving a moderate CYP3A4 inhibitor.
RanolazineCYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of ranolazine. Limit the ranolazine dose to a maximum of 500mg twice daily in patients concurrently receiving moderate CYP3A4 inhibitors (e.g., diltiazem, verapamil, erythromycin, etc.). Monitor for increased effects/toxicity of ranolazine during concomitant use.
TacrolimusThe antifungal, Clotrimazole, may increase serum concentrations of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Clotrimazole therapy is initiated, discontinued or altered.
TamsulosinClotrimazole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Clotrimazole is initiated, discontinued, or dose changed.
TolterodineClotrimazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
TolvaptanCYP3A4 Inhibitors (Moderate) may increase the serum concentration of tolvaptan. Coadministration of a strong CYP3A4 inhibitor with tolvaptan is contraindicated.
TramadolClotrimazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
TrazodoneThe CYP3A4 inhibitor, Clotrimazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Clotrimazole is initiated, discontinued or dose changed.
Food InteractionsNot Available

Targets

1. Lanosterol 14-alpha demethylase

Kind: protein

Organism: Yeast

Pharmacological action: yes

Actions: antagonist inhibitor

Components

Name UniProt ID Details
Lanosterol 14-alpha demethylase P10613 Details

References:

  1. 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. Epub 2010 Jul 12. Pubmed
  2. Gachotte D, Pierson CA, Lees ND, Barbuch R, Koegel C, Bard M: A yeast sterol auxotroph (erg25) is rescued by addition of azole antifungals and reduced levels of heme. Proc Natl Acad Sci U S A. 1997 Oct 14;94(21):11173-8. Pubmed
  3. Henry KW, Nickels JT, Edlind TD: Upregulation of ERG genes in Candida species by azoles and other sterol biosynthesis inhibitors. Antimicrob Agents Chemother. 2000 Oct;44(10):2693-700. Pubmed
  4. Lorenz RT, Parks LW: Physiological effects of fenpropimorph on wild-type Saccharomyces cerevisiae and fenpropimorph-resistant mutants. Antimicrob Agents Chemother. 1991 Aug;35(8):1532-7. Pubmed
  5. 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

2. Intermediate conductance calcium-activated potassium channel protein 4

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Intermediate conductance calcium-activated potassium channel protein 4 O15554 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Brugnara C, Gee B, Armsby CC, Kurth S, Sakamoto M, Rifai N, Alper SL, Platt OS: Therapy with oral clotrimazole induces inhibition of the Gardos channel and reduction of erythrocyte dehydration in patients with sickle cell disease. J Clin Invest. 1996 Mar 1;97(5):1227-34. Pubmed

Enzymes

1. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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
  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. Epub 2009 Nov 24. Pubmed
  3. Lexicomp

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, Kumar G, McLeod J, Obach SR, Roberts S, Roe A, Shah A, Snikeris F, Sullivan JT, Tweedie D, Vega JM, Walsh J, Wrighton SA: The conduct of in vitro and in vivo drug-drug interaction studies: a PhRMA perspective. J Clin Pharmacol. 2003 May;43(5):443-69. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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. Epub 2009 Nov 24. Pubmed
  4. Lexicomp

3. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. Pubmed
  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. Epub 2009 Nov 24. Pubmed
  3. Lexicomp

4. Cholesterol side-chain cleavage enzyme, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 Details

References:

  1. Mason JI, Murry BA, Olcott M, Sheets JJ: Imidazole antimycotics: inhibitors of steroid aromatase. Biochem Pharmacol. 1985 Apr 1;34(7):1087-92. Pubmed

5. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

6. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

7. Cytochrome P450 11B1, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 11B1, mitochondrial P15538 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 2A6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

10. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

11. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

12. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

13. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Canalicular multispecific organic anion transporter 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 2 O15438 Details

References:

  1. Teng S, Jekerle V, Piquette-Miller M: Induction of ABCC3 (MRP3) by pregnane X receptor activators. Drug Metab Dispos. 2003 Nov;31(11):1296-9. Pubmed

2. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. Pubmed
  2. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. Pubmed
  3. 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
  4. 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
  5. Bain LJ, LeBlanc GA: Interaction of structurally diverse pesticides with the human MDR1 gene product P-glycoprotein. Toxicol Appl Pharmacol. 1996 Nov;141(1):288-98. Pubmed
  6. 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

3. Canalicular multispecific organic anion transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 1 Q92887 Details

References:

  1. Kauffmann HM, Pfannschmidt S, Zoller H, Benz A, Vorderstemann B, Webster JI, Schrenk D: Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 09, 2014 12:21