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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Miconazole
- Accession Number
- DB01110 (APRD01115)
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Description
An imidazole antifungal agent that is used topically and by intravenous infusion.
- Structure
Structure for Miconazole (DB01110)
- Synonyms
- 1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
- 1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole
- Miconazol
- Miconazole
- Miconazolum
- External IDs
- MJR 1762 / R 18134
- Product Ingredients
Ingredient UNII CAS InChI Key Miconazole nitrate VW4H1CYW1K 22832-87-7 MCCACAIVAXEFAL-UHFFFAOYSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataMonistat 3 Suppository 200 mg/1 Vaginal ORTHO PHARMACEUTICAL CORPORATION 2006-12-31 Not applicable US 
Monistat-derm Cream 20 mg/1g Topical Ortho-McNeil Pharmaceutical, Inc. 2006-10-02 Not applicable US Oravig Tablet 50 mg/1 Buccal Praelia Pharmaceuticals Inc 2012-11-01 2015-09-30 US Oravig Tablet 50 mg/1 Buccal Par Pharmaceuticals Companies, Inc. 2010-04-26 2013-06-10 US 
Oravig Tablet 50 mg/1 Buccal Midatech Pharma Us, Inc. 2010-04-16 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataMiconazole Nitrate Suppository 200 mg/1 Vaginal Actavis Pharma, Inc. 1995-01-18 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional Data3M Cavilon Antifungal Cream 2 g/1000g Topical 3M Health Care 2010-11-30 Not applicable US 7 Day Vaginal Cream 2 g/100g Topical Cardinal Health 2009-03-16 Not applicable US Aloe Vesta Antifungal Ointment 20 mg/1g Topical ConvaTec, Inc. 1997-10-03 Not applicable US Aloe Vesta Clear Antifungal Ointment 2 g/100g Topical Convatec Inc. 2013-12-20 Not applicable US Aloe Vesta Clear Antifungal 141g Ointment 2.82 g/141g Topical Guest Packaging Llc. 2016-06-09 Not applicable US Aloe Vesta Clear Antifungal 56g Ointment 1.12 g/56g Topical Guest Packaging Llc. 2016-06-09 Not applicable US Anti-Fungal Cream 0.02 g/1g Topical Universal Distribution Center LLC 2015-04-15 Not applicable US Anti-Fungal Buttery Balm Lady Bits Ointment 2 g/100g Topical Derma Care Research Labs, LLC 2019-05-03 Not applicable US Antifungal Cream 20 mg/1g Topical PSS World Medical, Inc. 2012-09-05 Not applicable US Antifungal Cream 20 mg/1g Topical A-S Medication Solutions 1997-06-01 2017-12-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Antifungal Skin Care CVS Miconazole nitrate (2 g/100mL) + Benzalkonium chloride (0.12 g/100mL) Kit Topical Product Quest Mfg. 2016-04-14 2016-12-09 US Basic Care miconazole 1 Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical L. Perrigo Company 2017-08-29 Not applicable US Basic Care miconazole 1 Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical L. Perrigo Company 2017-08-29 Not applicable US Care One Miconazole 1 Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2010-11-19 Not applicable US Care One Miconazole 1 Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2010-11-19 Not applicable US Care One Miconazole 3 Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2004-07-27 2014-10-16 US Care One Miconazole 3 Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2004-07-27 2014-10-16 US CareOne Miconazole 3 Miconazole nitrate (4 g/100g) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2016-10-17 Not applicable US CareOne Miconazole 3 Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2014-04-13 Not applicable US CareOne Miconazole 3 Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g) Kit Topical American Sales Company 2014-04-13 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Onycho-Med Miconazole nitrate (200 mg/10mL) + Terbinafine hydrochloride (250 mg/250mg) Kit Topical Medhart Pharmaceuticals, Inc. 2019-04-16 Not applicable US - International/Other Brands
- Daktarin / Daktarin IV / Decocort / Femizol-M / Gyno-Daktarin / Miconazex / Monistat / Monistat IV / Zeasorb-AF / Zimycan
- Categories
- 14-alpha Demethylase Inhibitors
- Alimentary Tract and Metabolism
- Anti-Infective Agents
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antifungal Agents
- Antifungal Agents (Vaginal)
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Antiinfectives and Antiseptics for Local Oral Treatment
- Antiinfectives for Systemic Use
- Antimycotics for Systemic Use
- Azole Antifungals
- Chemically-Induced Disorders
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (strong)
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors (strong)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (moderate)
- Cytochrome P-450 CYP2C9 Inhibitors (strong)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strong)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Imidazole and Triazole Derivatives
- Imidazole Derivatives
- Imidazoles
- Intestinal Antiinfectives
- Otologicals
- P-glycoprotein inhibitors
- Sensory Organs
- Steroid Synthesis Inhibitors
- Stomatological Preparations
- Vaginal Creams, Foams, and Jellies
- UNII
- 7NNO0D7S5M
- CAS number
- 22916-47-8
- Weight
- Average: 416.129
Monoisotopic: 413.986023908 - Chemical Formula
- C18H14Cl4N2O
- InChI Key
- BYBLEWFAAKGYCD-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2
- IUPAC Name
- 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole
- SMILES
- ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1
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Pharmacology
- Indication
For topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor.
- Associated Conditions
- Pharmacodynamics
Miconazole is an anti-fungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). It is used either on the skin or in the vagina for fungal infections. Miconazole was approved by the FDA in 1974. Miconazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.
- Mechanism of action
Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
- Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half life
- Not Available
- Clearance
- Not Available
- Toxicity
Oral, mouse: LD50 = 3800 mg/kg; Oral, rat: LD50 = 3 gm/kg. Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects.
- Affected organisms
- Fungi, yeast and protozoans
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data(R)-warfarin The serum concentration of (R)-warfarin can be increased when it is combined with Miconazole. (S)-Warfarin The serum concentration of (S)-Warfarin can be increased when it is combined with Miconazole. 4-hydroxycoumarin The therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Miconazole. 4-Methoxyamphetamine The metabolism of 4-Methoxyamphetamine can be decreased when combined with Miconazole. 5-methoxy-N,N-dimethyltryptamine The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Miconazole. 9-aminocamptothecin The metabolism of 9-aminocamptothecin can be decreased when combined with Miconazole. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Miconazole. Acebutolol The serum concentration of Acebutolol can be increased when it is combined with Miconazole. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Miconazole. Acetaminophen Miconazole may increase the hepatotoxic activities of Acetaminophen. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- Synthesis Reference
- US3717655
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015242
- KEGG Drug
- D00882
- KEGG Compound
- C08070
- PubChem Compound
- 4189
- PubChem Substance
- 46506017
- ChemSpider
- 4044
- BindingDB
- 31772
- ChEBI
- 82892
- ChEMBL
- CHEMBL91
- Therapeutic Targets Database
- DAP000154
- PharmGKB
- PA450494
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Miconazole
- ATC Codes
- A07AC01 — Miconazole
- A07AC — Imidazole derivatives
- A07A — INTESTINAL ANTIINFECTIVES
- A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
- A — ALIMENTARY TRACT AND METABOLISM
- J02AB — Imidazole derivatives
- J02A — ANTIMYCOTICS FOR SYSTEMIC USE
- J02 — ANTIMYCOTICS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- A01AB — Antiinfectives and antiseptics for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- AHFS Codes
- 84:04.08.08 — Azoles
- FDA label
- Download (650 KB)
- MSDS
- Download (73.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Completed Treatment Intertrigo 1 0 Unknown Status Diagnostic Bacterial Vaginosis (BV) 1 1 Completed Diagnostic Endometriosis 1 1 Completed Prevention Human Immunodeficiency Virus (HIV) 1 1 Completed Treatment Healthy Volunteers 1 2 Completed Prevention Bacterial Vaginosis (BV) / Candidiasis infection / Trichomoniasis 1 2 Completed Treatment Otomycosis 1 2 Completed Treatment Tinea Cruris 1 2, 3 Recruiting Treatment Infections, Fungal 1 3 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 1 3 Completed Treatment Oral Candidiasis / Stomatitis, Denture 1 4 Completed Not Available Health / Vulvovaginal Candidiasis 1 4 Completed Treatment Diaper Rash 1 4 Completed Treatment Vulva; Candidiasis 1 4 Unknown Status Treatment Melasma 1 Not Available Completed Not Available Bacterial Vaginosis (BV) / Trichomonal Vaginitis / Vaginal Candidiasis 1 Not Available Completed Basic Science Healthy Volunteers 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Actavis Group
- Advanced Pharmaceutical Services Inc.
- Barr Pharmaceuticals
- CVS Pharmacy
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Draxis Specialty Pharmaceuticals Inc.
- Ivax Pharmaceuticals
- Johnson & Johnson Healthcare
- Kaiser Foundation Hospital
- Medisca Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Orthopedics Advanced Care
- Par Pharmaceuticals
- Perrigo Co.
- Pharmacia Inc.
- Pharmedix
- Physicians Total Care Inc.
- Prescript Pharmaceuticals
- Schering-Plough Inc.
- Southwood Pharmaceuticals
- Dosage forms
Form Route Strength Ointment Topical 20 mg/1g Ointment Topical 2.82 g/141g Ointment Topical 1.12 g/56g Cream Topical 2 mg/100mL Cream Topical 2 g/1000g Cream Topical 2.0 g/100mL Tincture Topical 20 mg/1mL Cream Topical 0.02 g/1g Spray Topical 20 mg/1g Cream Topical 0.02 g/100g Cream Topical Aerosol, powder Topical 2 g/100g Aerosol, spray Topical 2 g/100g Cream Topical 20 g/1000g Cream Topical 2.0 g/100g Ointment Topical 2.0 g/100g Powder Topical 2 g/100mL Kit Topical 20 mg/1mL Cream Topical 20 mg/1mL Powder Topical 20 mg/1g Aerosol, spray Topical 0.2 g/10g Cream Topical 2 g/100g Powder Topical 1.42 g/71g Aerosol, spray Topical 20 mg/1g Aerosol, powder Topical 20 mg/1g Liquid Topical 2 g/100g Cream Topical Aerosol Topical Powder Not applicable 1 g/1g Suppository Vaginal Cream Vaginal 2 mg/100g Cream Vaginal 20 mg/100g Suppository Vaginal 100 mg/1 Aerosol, powder Topical 2.6 g/130g Aerosol, spray Topical 1.3 g/131g Aerosol, spray Topical 1.3 g/130g Aerosol, spray Topical 2 g/150g Aerosol, spray Topical 2.6 g/130g Aerosol, spray Topical 3 g/150g Aerosol, spray Topical 3.0 g/150g Cream Topical 100 mg/2mg Cream Vaginal 20 mg/1g Powder Topical 2.6 g/130g Spray Topical 3 g/150g Suppository Vaginal 100 ug/1 Powder Topical 0.02 g/1g Cream Topical 0.3 g/14g Capsule; cream; kit Oral; Topical Suppository Vaginal 200 mg/1 Cream Vaginal 40 mg/1g Kit Vaginal Cream; insert Topical; Vaginal Insert Vaginal Cream; suppository Topical; Vaginal Cream Vaginal Cream Topical 20 mg/1g Cream Topical 200 mg/1mg Liquid Topical 20 mg/1mg Cream Topical .02 mL/1mL Tablet Buccal 50 mg/1 Liquid Topical Powder Topical 2 g/100g Ointment Topical 2 g/100g Cream Vaginal 2 g/100g Cream Topical 20 mg/100g Kit Topical Cream Topical 0.7 g/35g Aerosol, powder Topical 2.56 g/128g Paste Topical 2 g/100g Spray Topical 2 g/100g Kit Topical 200 mg/1 Liquid Topical 0.30 mg/15mL Ointment Topical Powder Topical 20.6 mg/1g - Prices
Unit description Cost Unit Vusion 0.25-15-81.35% Ointment 50 gm Tube 284.34USD tube Miconazole 3 3 200 mg Suppository Box 51.2USD box Monistat-Derm 2% Cream 28.35 gm Tube 41.99USD tube Monistat-Derm 2% Cream 15 gm Tube 32.0USD tube Monistat 1 combination pack 16.81USD each Monistat 7 combination pack 15.96USD each Miconazole Nitrate 2% Cream 28 gm Tube 12.99USD tube Miconazole powder 4.59USD g Monistat 1 6.5% ointment 3.6USD g Miconazole nitrate powder 3.55USD g Vusion ointment 3.17USD g Monistat-derm 2% cream 1.11USD g Miconazole nitrate 2% cream 0.19USD g CVS Pharmacy miconazole 7 cream 0.18USD g Miconazole 7 cream 0.15USD g Antifungal 2% cream 0.1USD g Micatin 2% aerosol spray 0.05USD g Lotrimin af 2% liquid spray 0.04USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS5514698 No 1996-05-07 2014-03-21 US US8147852 No 2012-04-03 2028-03-30 US US6153635 No 2000-11-28 2020-11-28 US US6916485 No 2005-07-12 2022-09-11 US US7651698 No 2010-01-26 2022-09-11 US US8518442 No 2013-08-27 2022-09-11 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 159-163 °C Not Available water solubility 1g/100mL (20 °C) Not Available logP 6.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000763 mg/mL ALOGPS logP 5.86 ALOGPS logP 5.96 ChemAxon logS -5.7 ALOGPS pKa (Strongest Basic) 6.77 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 27.05 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 103.07 m3·mol-1 ChemAxon Polarizability 39.54 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9735 Blood Brain Barrier + 0.9823 Caco-2 permeable + 0.6096 P-glycoprotein substrate Non-substrate 0.545 P-glycoprotein inhibitor I Non-inhibitor 0.7958 P-glycoprotein inhibitor II Inhibitor 0.8387 Renal organic cation transporter Inhibitor 0.6806 CYP450 2C9 substrate Non-substrate 0.8407 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7017 CYP450 1A2 substrate Inhibitor 0.9472 CYP450 2C9 inhibitor Inhibitor 0.939 CYP450 2D6 inhibitor Inhibitor 0.9413 CYP450 2C19 inhibitor Inhibitor 0.9591 CYP450 3A4 inhibitor Inhibitor 0.8861 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9961 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.853 Biodegradation Not ready biodegradable 0.9933 Rat acute toxicity 2.8478 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Inhibitor 0.8505
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzylethers
- Direct Parent
- Benzylethers
- Alternative Parents
- Dichlorobenzenes / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Benzylether / 1,3-dichlorobenzene / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / N-substituted imidazole / Imidazole / Azole / Heteroaromatic compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazoles, ether, dichlorobenzene (CHEBI:82892) / a small molecule (CPD-4501)
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
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- White TC, Marr KA, Bowden RA: Clinical, cellular, and molecular factors that contribute to antifungal drug resistance. Clin Microbiol Rev. 1998 Apr;11(2):382-402. [PubMed:9564569]
- Ghannoum MA, Rice LB: Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin Microbiol Rev. 1999 Oct;12(4):501-17. [PubMed:10515900]
- Edlind T, Smith L, Henry K, Katiyar S, Nickels J: Antifungal activity in Saccharomyces cerevisiae is modulated by calcium signalling. Mol Microbiol. 2002 Oct;46(1):257-68. [PubMed:12366848]
- Georgopapadakou NH, Walsh TJ: Antifungal agents: chemotherapeutic targets and immunologic strategies. Antimicrob Agents Chemother. 1996 Feb;40(2):279-91. [PubMed:8834867]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Tetrahydrobiopterin binding
- Specific Function
- Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
- Gene Name
- NOS3
- Uniprot ID
- P29474
- Uniprot Name
- Nitric oxide synthase, endothelial
- Molecular Weight
- 133287.62 Da
References
- Wolff DJ, Datto GA, Samatovicz RA: The dual mode of inhibition of calmodulin-dependent nitric-oxide synthase by antifungal imidazole agents. J Biol Chem. 1993 May 5;268(13):9430-6. [PubMed:7683652]
- Bogle RG, Whitley GS, Soo SC, Johnstone AP, Vallance P: Effect of anti-fungal imidazoles on mRNA levels and enzyme activity of inducible nitric oxide synthase. Br J Pharmacol. 1994 Apr;111(4):1257-61. [PubMed:7518297]
- Sennequier N, Wolan D, Stuehr DJ: Antifungal imidazoles block assembly of inducible NO synthase into an active dimer. J Biol Chem. 1999 Jan 8;274(2):930-8. [PubMed:9873034]
- Dudek RR, Conforto A, Pinto V, Wildhirt S, Suzuki H: Inhibition of endothelial nitric oxide synthase by cytochrome P-450 reductase inhibitors. Proc Soc Exp Biol Med. 1995 May;209(1):60-4. [PubMed:7536941]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Tetrahydrobiopterin binding
- Specific Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
- Gene Name
- NOS2
- Uniprot ID
- P35228
- Uniprot Name
- Nitric oxide synthase, inducible
- Molecular Weight
- 131116.3 Da
References
- Wolff DJ, Datto GA, Samatovicz RA: The dual mode of inhibition of calmodulin-dependent nitric-oxide synthase by antifungal imidazole agents. J Biol Chem. 1993 May 5;268(13):9430-6. [PubMed:7683652]
- Bogle RG, Whitley GS, Soo SC, Johnstone AP, Vallance P: Effect of anti-fungal imidazoles on mRNA levels and enzyme activity of inducible nitric oxide synthase. Br J Pharmacol. 1994 Apr;111(4):1257-61. [PubMed:7518297]
- Sennequier N, Wolan D, Stuehr DJ: Antifungal imidazoles block assembly of inducible NO synthase into an active dimer. J Biol Chem. 1999 Jan 8;274(2):930-8. [PubMed:9873034]
- Dudek RR, Conforto A, Pinto V, Wildhirt S, Suzuki H: Inhibition of endothelial nitric oxide synthase by cytochrome P-450 reductase inhibitors. Proc Soc Exp Biol Med. 1995 May;209(1):60-4. [PubMed:7536941]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activati...
- Gene Name
- KCNMA1
- Uniprot ID
- Q12791
- Uniprot Name
- Calcium-activated potassium channel subunit alpha-1
- Molecular Weight
- 137558.115 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Potassium channel regulator activity
- Specific Function
- Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Incr...
- Gene Name
- KCNMB1
- Uniprot ID
- Q16558
- Uniprot Name
- Calcium-activated potassium channel subunit beta-1
- Molecular Weight
- 21797.27 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Potassium channel regulator activity
- Specific Function
- Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Acts...
- Gene Name
- KCNMB2
- Uniprot ID
- Q9Y691
- Uniprot Name
- Calcium-activated potassium channel subunit beta-2
- Molecular Weight
- 27129.37 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Potassium channel regulator activity
- Specific Function
- Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Alte...
- Gene Name
- KCNMB3
- Uniprot ID
- Q9NPA1
- Uniprot Name
- Calcium-activated potassium channel subunit beta-3
- Molecular Weight
- 31603.26 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Potassium channel regulator activity
- Specific Function
- Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Decr...
- Gene Name
- KCNMB4
- Uniprot ID
- Q86W47
- Uniprot Name
- Calcium-activated potassium channel subunit beta-4
- Molecular Weight
- 23948.465 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Protein phosphatase binding
- Specific Function
- Forms a voltage-independent potassium channel that is activated by intracellular calcium (PubMed:26148990). Activation is followed by membrane hyperpolarization which promotes calcium influx. Requi...
- Gene Name
- KCNN4
- Uniprot ID
- O15554
- Uniprot Name
- Intermediate conductance calcium-activated potassium channel protein 4
- Molecular Weight
- 47695.12 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Small conductance calcium-activated potassium channel activity
- Specific Function
- Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to ...
- Gene Name
- KCNN1
- Uniprot ID
- Q92952
- Uniprot Name
- Small conductance calcium-activated potassium channel protein 1
- Molecular Weight
- 59986.87 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Small conductance calcium-activated potassium channel activity
- Specific Function
- Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to ...
- Gene Name
- KCNN2
- Uniprot ID
- Q9H2S1
- Uniprot Name
- Small conductance calcium-activated potassium channel protein 2
- Molecular Weight
- 63759.03 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Small conductance calcium-activated potassium channel activity
- Specific Function
- Forms a voltage-independent potassium channel activated by intracellular calcium. Activation is followed by membrane hyperpolarization. Thought to regulate neuronal excitability by contributing to ...
- Gene Name
- KCNN3
- Uniprot ID
- Q9UGI6
- Uniprot Name
- Small conductance calcium-activated potassium channel protein 3
- Molecular Weight
- 82025.305 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Alvarez J, Montero M, Garcia-Sancho J: High affinity inhibition of Ca(2+)-dependent K+ channels by cytochrome P-450 inhibitors. J Biol Chem. 1992 Jun 15;267(17):11789-93. [PubMed:1376313]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
- Specific Function
- Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
- Gene Name
- KCNH2
- Uniprot ID
- Q12809
- Uniprot Name
- Potassium voltage-gated channel subfamily H member 2
- Molecular Weight
- 126653.52 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Kikuchi K, Nagatomo T, Abe H, Kawakami K, Duff HJ, Makielski JC, January CT, Nakashima Y: Blockade of HERG cardiac K+ current by antifungal drug miconazole. Br J Pharmacol. 2005 Mar;144(6):840-8. [PubMed:15778703]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Pore-forming (alpha) subunit of voltage-gated potassium channel. Elicits a slowly activating, rectifying current (By similarity). Channel properties may be modulated by cAMP and subunit assembly.
- Gene Name
- KCNH6
- Uniprot ID
- Q9H252
- Uniprot Name
- Potassium voltage-gated channel subfamily H member 6
- Molecular Weight
- 109923.705 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Kikuchi K, Nagatomo T, Abe H, Kawakami K, Duff HJ, Makielski JC, January CT, Nakashima Y: Blockade of HERG cardiac K+ current by antifungal drug miconazole. Br J Pharmacol. 2005 Mar;144(6):840-8. [PubMed:15778703]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Pore-forming (alpha) subunit of voltage-gated potassium channel. Channel properties may be modulated by cAMP and subunit assembly.
- Gene Name
- KCNH7
- Uniprot ID
- Q9NS40
- Uniprot Name
- Potassium voltage-gated channel subfamily H member 7
- Molecular Weight
- 134998.525 Da
References
- Hatton CJ, Peers C: Effects of cytochrome P-450 inhibitors on ionic currents in isolated rat type I carotid body cells. Am J Physiol. 1996 Jul;271(1 Pt 1):C85-92. [PubMed:8760033]
- Kikuchi K, Nagatomo T, Abe H, Kawakami K, Duff HJ, Makielski JC, January CT, Nakashima Y: Blockade of HERG cardiac K+ current by antifungal drug miconazole. Br J Pharmacol. 2005 Mar;144(6):840-8. [PubMed:15778703]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [PubMed:17998298]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Draper AJ, Madan A, Parkinson A: Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Arch Biochem Biophys. 1997 May 1;341(1):47-61. doi: 10.1006/abbi.1997.9964. [PubMed:9143352]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Kind
- Protein
- Organism
- Humans
- 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 un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [PubMed:11854151]
- Potential CYP2B6 Substrates, Inhibitors, Inudcers (https://ctep.cancer.gov/protocoldevelopment/docs/cyp2b6.doc) [File]
- Kind
- Protein
- Organism
- Humans
- 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 un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567]
- Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [PubMed:10709776]
- Niwa T, Imagawa Y, Yamazaki H: Drug interactions between nine antifungal agents and drugs metabolized by human cytochromes P450. Curr Drug Metab. 2014;15(7):651-79. [PubMed:25429674]
- Kind
- Protein
- Organism
- Humans
- 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567]
- Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [PubMed:11854151]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Niwa T, Inoue-Yamamoto S, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 1A2, CYP2D6, and CYP2E1 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1813-6. [PubMed:16141569]
- Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [PubMed:11854151]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Niwa T, Inoue-Yamamoto S, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 1A2, CYP2D6, and CYP2E1 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1813-6. [PubMed:16141569]
- Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [PubMed:11854151]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [PubMed:9574817]
- Kind
- Protein
- Organism
- Humans
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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]
- Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [PubMed:15135088]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [PubMed:11854151]
- Niwa T, Imagawa Y, Yamazaki H: Drug interactions between nine antifungal agents and drugs metabolized by human cytochromes P450. Curr Drug Metab. 2014;15(7):651-79. [PubMed:25429674]
- Miconazole, Daily Med [Link]
- Kind
- Protein
- Organism
- Humans
- 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 cytochro...
- Gene Name
- CYP11B1
- Uniprot ID
- P15538
- Uniprot Name
- Cytochrome P450 11B1, mitochondrial
- Molecular Weight
- 57572.44 Da
References
- Denner K, Vogel R, Schmalix W, Doehmer J, Bernhardt R: Cloning and stable expression of the human mitochondrial cytochrome P45011B1 cDNA in V79 Chinese hamster cells and their application for testing of potential inhibitors. Pharmacogenetics. 1995 Apr;5(2):89-96. [PubMed:7663533]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 56805.26 Da
References
- Trosken ER, Scholz K, Lutz RW, Volkel W, Zarn JA, Lutz WK: Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans. Endocr Res. 2004 Aug;30(3):387-94. [PubMed:15554355]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Trosken ER, Scholz K, Lutz RW, Volkel W, Zarn JA, Lutz WK: Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans. Endocr Res. 2004 Aug;30(3):387-94. [PubMed:15554355]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- 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]
- 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]
- 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]
Drug created on June 13, 2005 07:24 / Updated on December 08, 2019 20:10