Identification

Name
Miconazole
Accession Number
DB01110
Description

Miconazole is a broad-spectrum azole antifungal with some activity against Gram-positive bacteria as well.3 It is widely used to treat mucosal yeast infections, including both oral and vaginal infections; although intravenous miconazole is no longer available, a wide variety of suppositories, creams, gels, and tablet-based products are available.13,14,15,16,17 Miconazole is thought to act primarily through the inhibition of fungal CYP450 14α-lanosterol demethylase activity.3,4

Miconazole was first synthesized in 1969 and first granted FDA approval on January 8, 1974, for sale by INSIGHT Pharmaceuticals as a topical cream.12,13 It is currently available as a variety of prescription and over the counter products. Despite having been in clinical use for an extended period, resistance to miconazole among susceptible organisms is relatively low.3

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 416.129
Monoisotopic: 413.986023908
Chemical Formula
C18H14Cl4N2O
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

Pharmacology

Indication

Miconazole is indicated for the local treatment of oropharyngeal candidiasis in adult patients and for the adjunctive treatment of diaper dermatitis complicated by candidiasis in immunocompetent patients aged four weeks and older.13,14 Miconazole is available as both a suppository and cream for the treatment of vaginal yeast infections and the relief of associated vulvar itching and irritation.15 Lastly, miconazole cream is effective in treating athlete's foot (tinea pedis), jock itch (tinea cruris), ringworm infections (tinea corporis),16 pityriasis (formerly tinea) versicolor,2 and cutaneous candidiasis.1

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Miconazole is an azole antifungal that functions primarily through inhibition of a specific demethylase within the CYP450 complex.3 As miconazole is typically applied topically and is minimally absorbed into the systemic circulation following application, the majority of patient reactions are limited to hypersensitivity and cases of anaphylaxis.13 Patients using intravaginal miconazole products are advised not to rely on contraceptives to prevent pregnancy and sexually transmitted infections, as well as not to use tampons concurrently.15

Mechanism of action

Miconazole is an azole antifungal used to treat a variety of conditions, including those caused by Candida overgrowth. Unique among the azoles, miconazole is thought to act through three main mechanisms.3 The primary mechanism of action is through inhibition of the CYP450 14α-lanosterol demethylase enzyme, which results in altered ergosterol production and impaired cell membrane composition and permeability, which in turn leads to cation, phosphate, and low molecular weight protein leakage.3,4

In addition, miconazole inhibits fungal peroxidase and catalase while not affecting NADH oxidase activity, leading to increased production of reactive oxygen species (ROS).3,4,5 Increased intracellular ROS leads to downstream pleiotropic effects and eventual apoptosis.3

Lastly, likely as a result of lanosterol demethylation inhibition, miconazole causes a rise in intracellular levels of farnesol. This molecule participates in quorum sensing in Candida, preventing the transition from yeast to mycelial forms and thereby the formation of biofilms, which are more resistant to antibiotics.6,7 In addition, farnesol is an inhibitor of drug efflux ABC transporters, namely Candida CaCdr1p and CaCdr2p, which may additionally contribute to increased effectiveness of azole drugs.7

TargetActionsOrganism
ACytochrome P450 51
inhibitor
Yeast
UNitric oxide synthase, endothelial
inhibitor
Humans
UNitric oxide synthase, inducible
inhibitor
Humans
UNuclear receptor subfamily 1 group I member 2
partial agonist
Humans
UCalcium-activated potassium channel
inhibitor
Humans
UVoltage-gated Potassium Channels
inhibitor
UInward rectifier potassium channel
inhibitor
Humans
UVoltage gated L-type calcium channel
inhibitor
Humans
Absorption

Miconazole given to healthy volunteers as a single 50 mg oral tablet produced a mean Cmax of 15.1 ± 16.2 mcg/mL, a mean AUC0-24 of 55.2 ± 35.1 mcg*h/mL, and a median Tmax of 7 hours (range 2.0-24.1). In these patients measurable plasma concentrations ranged from 0.5 to 0.83 mcg/mL.13

Topical miconazole is absorbed poorly into the systemic circulation.3 In pediatric patients aged 1-21 months given multiple topical applications of miconazole ointment for seven days, the plasma miconazole concentration was less than 0.5 ng/mL in 88% of the patients, with the remaining patients having a concentration of 0.57 and 0.58 ng/mL, respectively.14 Similarly, patients. administered with a vaginal 1200 mg ovule had a mean Cmax of 10.71 ng/mL, mean Tmax of 18.4 hours, and mean AUC0-96 of 477.3 ng*h/mL.9

Volume of distribution

A 1200 mg miconazole vaginal suppository resulted in a calculated apparent volume of distribution of 95 546 L while a 100 mg vaginal cream yielded an apparent volume of distribution of 10 911L.9

Protein binding

In vitro data suggests that miconazole binds human serum albumin, however, the clinical significance of this observation is unclear.10,11

Metabolism

Miconazole is metabolized in the liver and does not give rise to any active metabolites.13

Route of elimination

Miconazole is excreted through both urine and feces; less than 1% of unchanged miconazole is recovered in urine.13

Half-life

Miconazole has a terminal half-life of 24 hours.13

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Miconazole overdose has not been reported.13 Patients experiencing an overdose are at an increased risk of severe adverse effects such as headache, skin irritation, diarrhea, nausea, vomiting, abdominal pain, and dysgeusia. Symptomatic and supportive measures are recommended.

Miconazole has an oral LD50 of 500 mg/kg in rats.MSDS

Affected organisms
  • Fungi, yeast and protozoans
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Miconazole.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Miconazole.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Miconazole.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Miconazole.
AcetaminophenMiconazole may increase the hepatotoxic activities of Acetaminophen.
AcetohexamideThe serum concentration of Acetohexamide can be increased when it is combined with Miconazole.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Miconazole.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Miconazole.
AlectinibThe metabolism of Alectinib can be decreased when combined with Miconazole.
AlfuzosinThe metabolism of Alfuzosin can be decreased when combined with Miconazole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Miconazole nitrateVW4H1CYW1K22832-87-7MCCACAIVAXEFAL-UHFFFAOYSA-N
Product Images
International/Other Brands
Daktarin / Daktarin IV / Decocort / Femizol-M / Gyno-Daktarin / Miconazex / Monistat / Monistat IV / Zeasorb-AF / Zimycan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Monistat 3Suppository200 mg/1VaginalORTHO PHARMACEUTICAL CORPORATION2006-12-31Not applicableUS flag
Monistat-dermCream20 mg/1gTopicalOrtho-McNeil Pharmaceutical, Inc.2006-10-02Not applicableUS flag
OravigTablet50 mg/1BuccalMidatech Pharma Us, Inc.2010-04-16Not applicableUS flag
OravigTablet50 mg/1BuccalPar Pharmaceuticals Companies, Inc.2010-04-262013-06-10US flag49884 08220180907 15195 fo8j2r
OravigTablet50 mg/1BuccalPraelia Pharmaceuticals Inc2012-11-012015-09-30US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Miconazole NitrateSuppository200 mg/1VaginalActavis Pharma, Inc.1995-01-18Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
3M Cavilon AntifungalCream2 g/1000gTopical3M Company2010-11-30Not applicableUS flag
7 Day VaginalCream2 g/100gTopicalCardinal Health2009-03-16Not applicableUS flag
Aloe Vesta AntifungalOintment20 mg/1gTopicalConvaTec, Inc.1997-10-03Not applicableUS flag
Aloe Vesta Clear AntifungalOintment2 g/100gTopicalConvatec Inc.2013-12-20Not applicableUS flag
Aloe Vesta Clear Antifungal 141gOintment2.82 g/141gTopicalGuest Packaging Llc.2016-06-09Not applicableUS flag
Aloe Vesta Clear Antifungal 56gOintment1.12 g/56gTopicalGuest Packaging Llc.2016-06-09Not applicableUS flag
Anti-FungalCream0.02 g/1gTopicalUniversal Distribution Center LLC2015-04-15Not applicableUS flag
Anti-Fungal Buttery Balm Lady BitsOintment2 g/100gTopicalDerma Care Research Labs, LLC2019-05-03Not applicableUS flag
AntifungalCream20 mg/1gTopicalPreferred Pharmaceuticals Inc.2016-08-25Not applicableUS flag
AntifungalCream20 mg/1gTopicalPSS World Medical, Inc.2012-09-05Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Antifungal Skin Care CVSMiconazole nitrate (2 g/100mL) + Benzalkonium chloride (0.12 g/100mL)KitTopicalProduct Quest Mfg.2016-04-142016-12-09US flag
Basic Care miconazole 1Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalL. Perrigo Company2017-08-29Not applicableUS flag
Basic Care miconazole 1Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalL. Perrigo Company2017-08-29Not applicableUS flag
Care One Miconazole 1Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalAmerican Sales Company2010-11-19Not applicableUS flag
Care One Miconazole 1Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalAmerican Sales Company2010-11-19Not applicableUS flag
Care One Miconazole 3Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalAmerican Sales Company2004-07-272014-10-16US flag
Care One Miconazole 3Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalAmerican Sales Company2004-07-272014-10-16US flag
Careone Miconazole 1Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)Topical; VaginalAmerican Sales Company2020-01-15Not applicableUS flag
Careone Miconazole 1Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)Topical; VaginalAmerican Sales Company2020-01-15Not applicableUS flag
CareOne Miconazole 3Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)KitTopical; VaginalAmerican Sales Company2014-04-13Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Onycho-MedMiconazole nitrate (200 mg/10mL) + Terbinafine hydrochloride (250 mg/250mg)KitTopicalMedhart Pharmaceuticals, Inc.2019-04-16Not applicableUS flag

Categories

ATC Codes
A07AC01 — MiconazoleJ02AB01 — MiconazoleD01AC52 — Miconazole, combinationsG01AF20 — Combinations of imidazole derivativesA01AB09 — MiconazoleD01AC02 — MiconazoleS02AA13 — MiconazoleG01AF04 — Miconazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzylether / Chlorobenzene / Dialkyl ether / Ether
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, ether, dichlorobenzene (CHEBI:82892) / a small molecule (CPD-4501)

Chemical Identifiers

UNII
7NNO0D7S5M
CAS number
22916-47-8
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

References

Synthesis Reference

Godefroi EF, Heeres J, Van Cutsem J, Janssen PA: The preparation and antimycotic properties of derivatives of 1-phenethylimidazole. J Med Chem. 1969 Sep;12(5):784-91. doi: 10.1021/jm00305a014.

US3717655
General References
  1. Taudorf EH, Jemec GBE, Hay RJ, Saunte DML: Cutaneous candidiasis - an evidence-based review of topical and systemic treatments to inform clinical practice. J Eur Acad Dermatol Venereol. 2019 Oct;33(10):1863-1873. doi: 10.1111/jdv.15782. Epub 2019 Jul 30. [PubMed:31287594]
  2. Tanenbaum L, Anderson C, Rosenberg MJ, Akers W: 1% sulconazole cream v 2% miconazole cream in the treatment of tinea versicolor. A double-blind, multicenter study. Arch Dermatol. 1984 Feb;120(2):216-9. [PubMed:6364994]
  3. Pierard GE, Hermanns-Le T, Delvenne P, Pierard-Franchimont C: Miconazole, a pharmacological barrier to skin fungal infections. Expert Opin Pharmacother. 2012 Jun;13(8):1187-94. doi: 10.1517/14656566.2012.687047. Epub 2012 May 8. [PubMed:22568580]
  4. De Nollin S, Borgers M: An ultrastructural and cytochemical study of Candida albicans after in vitro treatment with imidazoles. Mykosen. 1976 Sep;19(9):317-28. doi: 10.1111/j.1439-0507.1976.tb01469.x. [PubMed:185515]
  5. Kobayashi D, Kondo K, Uehara N, Otokozawa S, Tsuji N, Yagihashi A, Watanabe N: Endogenous reactive oxygen species is an important mediator of miconazole antifungal effect. Antimicrob Agents Chemother. 2002 Oct;46(10):3113-7. doi: 10.1128/aac.46.10.3113-3117.2002. [PubMed:12234832]
  6. Hornby JM, Nickerson KW: Enhanced production of farnesol by Candida albicans treated with four azoles. Antimicrob Agents Chemother. 2004 Jun;48(6):2305-7. doi: 10.1128/AAC.48.6.2305-2307.2004. [PubMed:15155241]
  7. Sharma M, Prasad R: The quorum-sensing molecule farnesol is a modulator of drug efflux mediated by ABC multidrug transporters and synergizes with drugs in Candida albicans. Antimicrob Agents Chemother. 2011 Oct;55(10):4834-43. doi: 10.1128/AAC.00344-11. Epub 2011 Jul 18. [PubMed:21768514]
  8. Thevissen K, Ayscough KR, Aerts AM, Du W, De Brucker K, Meert EM, Ausma J, Borgers M, Cammue BP, Francois IE: Miconazole induces changes in actin cytoskeleton prior to reactive oxygen species induction in yeast. J Biol Chem. 2007 Jul 27;282(30):21592-7. doi: 10.1074/jbc.M608505200. Epub 2007 Jun 6. [PubMed:17553796]
  9. Stevens RE, Konsil J, Verrill SS, Roy P, Desai PB, Upmalis DH, Cone FL: Bioavailability study of a 1200 mg miconazole nitrate vaginal ovule in healthy female adults. J Clin Pharmacol. 2002 Jan;42(1):52-60. doi: 10.1177/0091270002042001006. [PubMed:11808824]
  10. Schafer-Korting M, Korting HC, Rittler W, Obermuller W: Influence of serum protein binding on the in vitro activity of anti-fungal agents. Infection. 1995 Sep-Oct;23(5):292-7. doi: 10.1007/bf01716289. [PubMed:8557388]
  11. Hu Z, Zhang J, Cheng X: Antifungal efficiency of miconazole and econazole and the interaction with transport protein: a comparative study. Pharm Biol. 2015 Feb;53(2):251-61. doi: 10.3109/13880209.2014.914232. Epub 2014 Nov 7. [PubMed:25376919]
  12. Godefroi EF, Heeres J, Van Cutsem J, Janssen PA: The preparation and antimycotic properties of derivatives of 1-phenethylimidazole. J Med Chem. 1969 Sep;12(5):784-91. doi: 10.1021/jm00305a014. [PubMed:4897900]
  13. FDA Approved Drug Products: Oravig (miconazole) buccal tablet [Link]
  14. FDA Approved Drug Products: Vusion (miconazole nitrate, zinc oxide, white petrolatum) topical ointment [Link]
  15. FDA Approved Drug Products: miconazole nitrate suppositories and cream [Link]
  16. DailyMed miconazole nitrate [Link]
  17. FDA Approved Drug Products: Monistat (miconazole nitrate) suppositories and cream [Link]
Human Metabolome Database
HMDB0015242
KEGG Drug
D00882
KEGG Compound
C08070
PubChem Compound
4189
PubChem Substance
46506017
ChemSpider
4044
BindingDB
31772
RxNav
6932
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
AHFS Codes
  • 84:04.08.08 — Azoles
FDA label
Download (650 KB)
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableHealth / Vulvovaginal Candidiasis1
4CompletedTreatmentDiaper Rash1
4CompletedTreatmentVulva; Candidiasis1
4Unknown StatusTreatmentMelasma1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentOral Candidiasis / Stomatitis, Denture1
2CompletedPreventionBacterial Vaginosis (BV) / Candidiasis / Trichomoniasis1
2CompletedTreatmentOtomycosis1
2CompletedTreatmentTinea Cruris1
2RecruitingPreventionOral Mucositis Due to Chemotherapy1

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
FormRouteStrength
CreamTopical25 %
OintmentTopical20 mg/1g
OintmentTopical2.82 g/141g
OintmentTopical1.12 g/56g
CreamTopical2 mg/100mL
CreamTopical2 g/1000g
CreamTopical2.0 g/100mL
Tablet
SprayTopical2 g/100g
TinctureTopical20 mg/1mL
Cream100 mg/100g
CreamTopical0.02 g/1g
SolutionOral20 mg/g
Cream2 g/100g
GelOral2 g/100g
CreamTopical2 %
SolutionTopical2 %
Cream
Gel
Liquid
CreamTopical0.02 g/100g
CreamTopical
Aerosol, powderTopical2 g/100g
Aerosol, sprayTopical2 g/100g
CreamTopical2 g/100mL
EmulsionTopical0.1 %
TabletVaginal750 mg
InsertVaginal1200 mg
CreamTopical2.0 g/100g
OintmentTopical2.0 g/100g
PowderTopical2 g/100mL
KitTopical20 mg/1mL
LotionTopical20 mg/1mL
CreamTopical20 mg/1mL
CreamVaginal20 mg
InsertVaginal750 mg
SuspensionTopical2 g
Aerosol, sprayTopical0.2 g/10g
CreamTopical2 g/100g
Cream1 g/100g
PowderTopical1.42 g/71g
SuppositoryVaginal750 mg
SuppositoryVaginal750 mg/200g
TabletOral50 MG
Aerosol, sprayTopical20 mg/1g
Aerosol, powderTopical20 mg/1g
SprayCutaneous2 %
LiquidTopical2 g/100g
SprayTopical20 mg/1g
CreamTopical
AerosolTopical
CreamTopical20 mg/g
SolutionOral20 mg/ml
PowderNot applicable1 g/1g
KitTopical; Vaginal
SuppositoryVaginal
CreamVaginal100 mg/1g
CreamVaginal2 mg/100g
CreamVaginal20 mg/100g
SuppositoryVaginal100 mg/1
Aerosol, powderTopical2.6 g/130g
Aerosol, sprayTopical1.3 g/130g
Aerosol, sprayTopical2 g/150g
Aerosol, sprayTopical2.6 g/130g
Aerosol, sprayTopical3 g/150g
CreamTopical100 mg/2mg
CreamVaginal20 mg/1g
PowderTopical2.6 g/130g
SprayTopical3 g/150g
SuppositoryVaginal100 ug/1
Aerosol, sprayTopical1.3 g/131g
Suppository1200 mg
Powder
PowderTopical0.02 g/1g
SuppositoryVaginal200 mg
CreamTopical0.3 g/14g
Capsule; cream; kitOral; Topical
SuppositoryVaginal200 mg/1
CreamVaginal40 mg/1g
KitVaginal
Cream; insertTopical; Vaginal
InsertVaginal
Cream; suppositoryTopical; Vaginal
CreamVaginal
CreamTopical20 mg/1g
PowderTopical
CreamTopical200 mg/1mg
LiquidTopical20 mg/1mg
SuppositoryVaginal500 mg
Tablet500 mg
AerosolTopical2 g
CreamCutaneous2 g
CreamCutaneous; Vaginal2 g
PowderTopical2 %
TabletOral250 MG
TabletOral500 MG
CreamTopical.02 mL/1mL
TabletBuccal50 mg/1
GelTopical19 %
CapsuleVaginal1200 MG
CapsuleVaginal400 MG
SolutionVaginal0.2 %
CreamTopical20 g/1000g
LiquidTopical
PowderTopical2 g/100g
PowderTopical20 mg/1g
OintmentTopical2 g/100g
CreamTopical20 mg/100g
SuppositoryVaginal100 mg
KitTopical
CreamTopical0.7 g/35g
Aerosol, powderTopical2.56 g/128g
PasteTopical2 g/100g
CreamVaginal2 g/100g
KitTopical; Vaginal200 mg/1
LiquidTopical0.30 mg/15mL
OintmentTopical
PowderTopical20.6 mg/1g
Prices
Unit descriptionCostUnit
Vusion 0.25-15-81.35% Ointment 50 gm Tube284.34USD tube
Miconazole 3 3 200 mg Suppository Box51.2USD box
Monistat-Derm 2% Cream 28.35 gm Tube41.99USD tube
Monistat-Derm 2% Cream 15 gm Tube32.0USD tube
Monistat 1 combination pack16.81USD each
Monistat 7 combination pack15.96USD each
Miconazole Nitrate 2% Cream 28 gm Tube12.99USD tube
Miconazole powder4.59USD g
Monistat 1 6.5% ointment3.6USD g
Miconazole nitrate powder3.55USD g
Vusion ointment3.17USD g
Monistat-derm 2% cream1.11USD g
Miconazole nitrate 2% cream0.19USD g
CVS Pharmacy miconazole 7 cream0.18USD g
Miconazole 7 cream0.15USD g
Antifungal 2% cream0.1USD g
Micatin 2% aerosol spray0.05USD g
Lotrimin af 2% liquid spray0.04USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5514698No1996-05-072014-03-21US flag
US8147852No2012-04-032028-03-30US flag
US6153635No2000-11-282020-11-28US flag
US6916485No2005-07-122022-09-11US flag
US7651698No2010-01-262022-09-11US flag
US8518442No2013-08-272022-09-11US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)170MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.000763 mg/mLALOGPS
logP5.86ALOGPS
logP5.96ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.07 m3·mol-1ChemAxon
Polarizability39.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9735
Blood Brain Barrier+0.9823
Caco-2 permeable+0.6096
P-glycoprotein substrateNon-substrate0.545
P-glycoprotein inhibitor INon-inhibitor0.7958
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterInhibitor0.6806
CYP450 2C9 substrateNon-substrate0.8407
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7017
CYP450 1A2 substrateInhibitor0.9472
CYP450 2C9 inhibitorInhibitor0.939
CYP450 2D6 inhibitorInhibitor0.9413
CYP450 2C19 inhibitorInhibitor0.9591
CYP450 3A4 inhibitorInhibitor0.8861
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9961
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.853
BiodegradationNot ready biodegradable0.9933
Rat acute toxicity2.8478 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.8505
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0bt9-4900000000-3f143064c2acde7e15a4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02t9-0501900000-40f5928152d84e02deef
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-2900000000-1921b08c2de7bbf0624d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0bt9-0900500000-1a5805da9606edbe7e9a

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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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
Partial agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [PubMed:17998298]
Kind
Protein group
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...

Components:
References
  1. 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]
  2. 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 group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
Voltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain and the central nervous system, but also in the kidney (PubMed:1990381...

Components:
NameUniProt ID
Potassium voltage-gated channel subfamily A member 1Q09470
Potassium voltage-gated channel subfamily A member 10Q16322
Potassium voltage-gated channel subfamily A member 2P16389
Potassium voltage-gated channel subfamily A member 3P22001
Potassium voltage-gated channel subfamily A member 4P22459
Potassium voltage-gated channel subfamily A member 5P22460
Potassium voltage-gated channel subfamily A member 6P17658
Potassium voltage-gated channel subfamily B member 1Q14721
Potassium voltage-gated channel subfamily B member 2Q92953
Potassium voltage-gated channel subfamily C member 1P48547
Potassium voltage-gated channel subfamily C member 2Q96PR1
Potassium voltage-gated channel subfamily C member 3Q14003
Potassium voltage-gated channel subfamily C member 4Q03721
Potassium voltage-gated channel subfamily D member 1Q9NSA2
Potassium voltage-gated channel subfamily D member 2Q9NZV8
Potassium voltage-gated channel subfamily D member 3Q9UK17
Potassium voltage-gated channel subfamily E member 1P15382
Potassium voltage-gated channel subfamily E member 2Q9Y6J6
Potassium voltage-gated channel subfamily E member 3Q9Y6H6
Potassium voltage-gated channel subfamily E member 4Q8WWG9
Potassium voltage-gated channel subfamily E regulatory beta subunit 5Q9UJ90
Potassium voltage-gated channel subfamily F member 1Q9H3M0
Potassium voltage-gated channel subfamily G member 1Q9UIX4
Potassium voltage-gated channel subfamily G member 2Q9UJ96
Potassium voltage-gated channel subfamily G member 3Q8TAE7
Potassium voltage-gated channel subfamily G member 4Q8TDN1
Potassium voltage-gated channel subfamily H member 1O95259
Potassium voltage-gated channel subfamily H member 2Q12809
Potassium voltage-gated channel subfamily H member 3Q9ULD8
Potassium voltage-gated channel subfamily H member 4Q9UQ05
Potassium voltage-gated channel subfamily H member 5Q8NCM2
Potassium voltage-gated channel subfamily H member 6Q9H252
Potassium voltage-gated channel subfamily H member 7Q9NS40
Potassium voltage-gated channel subfamily H member 8Q96L42
Potassium voltage-gated channel subfamily KQT member 1P51787
Potassium voltage-gated channel subfamily KQT member 2O43526
Potassium voltage-gated channel subfamily KQT member 3O43525
Potassium voltage-gated channel subfamily KQT member 4P56696
Potassium voltage-gated channel subfamily KQT member 5Q9NR82
Potassium voltage-gated channel subfamily S member 1Q96KK3
Potassium voltage-gated channel subfamily S member 3Q9BQ31
Potassium voltage-gated channel subfamily V member 1Q6PIU1
Potassium voltage-gated channel subfamily V member 2Q8TDN2
Voltage-gated potassium channel subunit beta-1Q14722
Voltage-gated potassium channel subunit beta-2Q13303
References
  1. 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]
  2. 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]
  3. Sung DJ, Kim JG, Won KJ, Kim B, Shin HC, Park JY, Bae YM: Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Biol Pharm Bull. 2012;35(9):1469-75. doi: 10.1248/bpb.b12-00002. [PubMed:22975497]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Inward rectifier potassium channel activity
Specific Function
Inward rectifying potassium channel that is activated by phosphatidylinositol 4,5-bisphosphate and that probably participates in controlling the resting membrane potential in electrically excitable...

Components:
References
  1. Sung DJ, Kim JG, Won KJ, Kim B, Shin HC, Park JY, Bae YM: Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Biol Pharm Bull. 2012;35(9):1469-75. doi: 10.1248/bpb.b12-00002. [PubMed:22975497]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...

Components:
References
  1. Sung DJ, Kim JG, Won KJ, Kim B, Shin HC, Park JY, Bae YM: Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Biol Pharm Bull. 2012;35(9):1469-75. doi: 10.1248/bpb.b12-00002. [PubMed:22975497]

Enzymes

Details
1. Cytochrome P450 2C9
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Flockhart Table of Drug Interactions [Link]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
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
  1. 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]
  2. 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]
  3. 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]
  4. Flockhart Table of Drug Interactions [Link]
  5. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
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
  1. 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]
  2. 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]
  3. 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]
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Flockhart Table of Drug Interactions [Link]
Details
5. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Flockhart Table of Drug Interactions [Link]
  7. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  8. FDA Approved Drug Products: Oravig (miconazole) buccal tablet [Link]
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
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  4. 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
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
  1. 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]
  2. 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]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Niwa T, Imagawa Y: Substrate Specificity of Human Cytochrome P450 (CYP) 2C Subfamily and Effect of Azole Antifungal Agents on CYP2C8. J Pharm Pharm Sci. 2016 Oct - Dec;19(4):423-429. doi: 10.18433/J31S53. [PubMed:28057172]
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
  1. 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]
  2. 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
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
  1. 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]
  2. 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
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. 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]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Hu Z, Zhang J, Cheng X: Antifungal efficiency of miconazole and econazole and the interaction with transport protein: a comparative study. Pharm Biol. 2015 Feb;53(2):251-61. doi: 10.3109/13880209.2014.914232. Epub 2014 Nov 7. [PubMed:25376919]
  2. Schafer-Korting M, Korting HC, Rittler W, Obermuller W: Influence of serum protein binding on the in vitro activity of anti-fungal agents. Infection. 1995 Sep-Oct;23(5):292-7. doi: 10.1007/bf01716289. [PubMed:8557388]

Transporters

Details
1. P-glycoprotein 1
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]

Drug created on June 13, 2005 07:24 / Updated on October 19, 2020 07:47

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