Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Monistat 3	Suppository	200 mg/1	Vaginal	ORTHO PHARMACEUTICAL CORPORATION	2006-12-31	Not applicable
Monistat-derm	Cream	20 mg/1g	Topical	Ortho-McNeil Pharmaceutical, Inc.	2006-10-02	Not applicable
Oravig	Tablet	50 mg/1	Buccal	Praelia Pharmaceuticals Inc	2012-11-01	2015-09-30
Oravig	Tablet	50 mg/1	Buccal	Par Pharmaceuticals Companies, Inc.	2010-04-26	2013-06-10
Oravig	Tablet	50 mg/1	Buccal	Midatech Pharma Us, Inc.	2010-04-16	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Miconazole Nitrate	Suppository	200 mg/1	Vaginal	Actavis Pharma Company	1995-01-18	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
3M Cavilon Antifungal	Cream	2 g/1000g	Topical	3 M Pharmaceuticals	2010-11-30	Not applicable
7 Day Vaginal	Cream	2 g/100g	Topical	Cardinal Health	2009-03-16	Not applicable
Aloe Vesta Antifungal	Ointment	20 mg/1g	Topical	ConvaTec, Inc.	1997-10-03	Not applicable
Aloe Vesta Clear Antifungal	Ointment	2 g/100g	Topical	Convatec Inc.	2013-12-20	Not applicable
Aloe Vesta Clear Antifungal 141g	Ointment	2.82 g/141g	Topical	Guest Packaging Llc.	2016-06-09	Not applicable
Aloe Vesta Clear Antifungal 56g	Ointment	1.12 g/56g	Topical	Guest Packaging Llc.	2016-06-09	Not applicable
Anti-Fungal	Cream	0.02 g/1g	Topical	Universal Distribution Center LLC	2015-04-15	Not applicable
Antifungal	Cream	2 mg/100mL	Topical	Mc Kesson	2017-05-26	Not applicable
Antifungal	Cream	20 mg/1g	Topical	Proficient Rx LP	2007-05-01	Not applicable
Antifungal	Cream	20 mg/1g	Topical	A-S Medication Solutions	1997-06-01	2017-12-31

Mixture Products

Name	Ingredients	Dosage	Labeller	Marketing Start	Marketing End
Antifungal Skin Care CVS	Miconazole nitrate (2 g/100mL) + Benzalkonium chloride (0.12 g/100mL)	Kit	Product Quest Mfg.	2016-04-14	2016-12-09
Basic Care miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	L. Perrigo Company	2017-08-29	Not applicable
Basic Care miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	L. Perrigo Company	2017-08-29	Not applicable
Care One Miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2010-11-19	Not applicable
Care One Miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2010-11-19	Not applicable
Care One Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2004-07-27	2014-10-16
Care One Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2004-07-27	2014-10-16
CareOne Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2014-04-13	Not applicable
CareOne Miconazole 3	Miconazole nitrate (4 g/100g) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2016-10-17	Not applicable
CareOne Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	American Sales Company	2014-04-13	Not applicable

International/Other Brands

Daktarin / Daktarin IV / Decocort / Femizol-M / Gyno-Daktarin / Miconazex / Monistat / Monistat IV / Monistat-Derm / Zeasorb-AF / Zimycan

Categories

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

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.

Target	Actions	Organism
ALanosterol 14-alpha demethylase	inhibitor	Yeast
UNitric oxide synthase, endothelial	inhibitor	Human
UNitric oxide synthase, inducible	inhibitor	Human
UCalcium-activated potassium channel subunit alpha-1	inhibitor	Human
UCalcium-activated potassium channel subunit beta-1	inhibitor	Human
UCalcium-activated potassium channel subunit beta-2	inhibitor	Human
UCalcium-activated potassium channel subunit beta-3	inhibitor	Human
UCalcium-activated potassium channel subunit beta-4	inhibitor	Human
UIntermediate conductance calcium-activated potassium channel protein 4	inhibitor	Human
USmall conductance calcium-activated potassium channel protein 1	inhibitor	Human
USmall conductance calcium-activated potassium channel protein 2	inhibitor	Human
USmall conductance calcium-activated potassium channel protein 3	inhibitor	Human
UPotassium voltage-gated channel subfamily H member 2	inhibitor	Human
UPotassium voltage-gated channel subfamily H member 6	inhibitor	Human
UPotassium voltage-gated channel subfamily H member 7	inhibitor	Human
UNuclear receptor subfamily 1 group I member 2	partial agonist	Human

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

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Miconazole.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Miconazole.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Miconazole.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Miconazole.
4-Methoxyamphetamine	The metabolism of 4-Methoxyamphetamine can be decreased when combined with Miconazole.
5-androstenedione	The metabolism of 5-androstenedione can be decreased when combined with Miconazole.
6-Deoxyerythronolide B	The metabolism of Miconazole can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Miconazole.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Miconazole.
Abiraterone	The metabolism of Abiraterone can be decreased when combined with Miconazole.

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
IUPHAR: 2449
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Miconazole

ATC Codes

G01AF20 — Combinations of imidazole derivatives

G01AF04 — Miconazole

D01AC52 — Miconazole, combinations

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
1	Completed	Diagnostic	Endometriosis	1
1	Completed	Prevention	Human Immunodeficiency Virus (HIV)	1
1	Completed	Treatment	Autoimmune Diseases / Disseminated or Multiple Sclerosis Nos / Disseminated Sclerosis / Multiple Sclerosis, Acute Relapsing / Multiple Sclerosis, Chronic Progressive / Multiple Sclerosis, Primary Progressive	1
1	Completed	Treatment	Healthy Volunteers	1
2	Completed	Treatment	Tinea Cruris	1
2	Recruiting	Treatment	Otomycosis	1
2, 3	Not Yet Recruiting	Treatment	Candidiasis infection	1
2, 3	Recruiting	Treatment	Infections, Fungal	1
3	Completed	Treatment	Oral Candidiasis / Stomatitis, Denture	1
4	Completed	Not Available	Health / Vulvovaginal Candidiasis	1
4	Completed	Treatment	Diaper Rash	1
4	Not Yet Recruiting	Treatment	Sleep Initiation and Maintenance Disorders / Stress Disorders, Posttraumatic	1
4	Recruiting	Treatment	Bacterial Vaginosis (BV) / Candidiasis infection	1
4	Unknown Status	Treatment	Melasma	1
4	Unknown Status	Treatment	Onychomycosis	1
Not Available	Completed	Not Available	Bacterial Vaginosis (BV) / Trichomonal Vaginitis / Vaginal Candidiasis	1
Not Available	Completed	Basic Science	Healthy Volunteers	1
Not Available	No Longer Available	Not Available	Diabetes, Diabetes Mellitus Type 1	1
Not Available	Unknown Status	Treatment	Onychomycosis	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
Cream	Topical	2 g/1000g
Ointment	Topical	20 mg/1g
Ointment	Topical	2.82 g/141g
Ointment	Topical	1.12 g/56g
Cream	Topical	2 mg/100mL
Cream	Topical	2.0 g/100mL
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
Tincture	Topical	20 mg/1mL
Kit		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
Aerosol, spray	Topical	2.6 g/130g
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	2 %
Aerosol	Topical	2 %
Kit	Topical; Vaginal
Kit	Vaginal
Suppository	Vaginal	400 mg
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/130g
Aerosol, spray	Topical	1.3 g/131g
Aerosol, spray	Topical	2.0 g/150g
Aerosol, spray	Topical	3 g/150g
Aerosol, spray	Topical	3.0 g/150g
Cream	Vaginal	20 mg/1g
Cream	Vaginal	40 mg/1g
Powder	Topical	2.6 g/130g
Spray	Topical	3.0 g/150g
Suppository	Vaginal	100 ug/1
Powder	Topical	0.02 g/1g
Cream	Topical	0.3 g/14g
Cream	Vaginal	20 mg
Capsule; cream; kit	Oral; Topical
Suppository	Vaginal	1200 mg
Suppository	Vaginal	200 mg/1
Cream; insert	Topical; Vaginal
Cream	Vaginal	4 %
Insert	Vaginal	400 mg
Cream; suppository	Topical; Vaginal
Suppository	Vaginal	100 mg
Cream	Vaginal	2 %
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
Cream	Vaginal	2 g/100g
Cream	Topical	20 mg/100g
Kit
Cream	Topical	0.7 g/35g
Aerosol, powder	Topical	2.56 g/128g
Ointment	Topical	2 g/100g
Spray	Topical	2 g/100g
Kit		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)
US5514698	No	1996-05-07	2014-03-21
US8147852	No	2012-04-03	2028-03-30
US6153635	No	2000-11-28	2020-11-28
US6916485	No	2005-07-12	2022-09-11
US7651698	No	2010-01-26	2022-09-11
US8518442	No	2013-08-27	2022-09-11

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-0bt9-4900000000-3f143064c2acde7e15a4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-02t9-0501900000-40f5928152d84e02deef
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0bt9-2900000000-1921b08c2de7bbf0624d
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0bt9-0900500000-1a5805da9606edbe7e9a

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

Details1. Lanosterol 14-alpha demethylase

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]

Details2. Nitric oxide synthase, endothelial

Kind: Protein
Organism: Human
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]

Details3. Nitric oxide synthase, inducible

Kind: Protein
Organism: Human
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]

Details4. Calcium-activated potassium channel subunit alpha-1

Kind: Protein
Organism: Human
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]

Details5. Calcium-activated potassium channel subunit beta-1

Kind: Protein
Organism: Human
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]

Details6. Calcium-activated potassium channel subunit beta-2

Kind: Protein
Organism: Human
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]

Details7. Calcium-activated potassium channel subunit beta-3

Kind: Protein
Organism: Human
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]

Details8. Calcium-activated potassium channel subunit beta-4

Kind: Protein
Organism: Human
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]

Details9. Intermediate conductance calcium-activated potassium channel protein 4

Kind: Protein
Organism: Human
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]

Details10. Small conductance calcium-activated potassium channel protein 1

Kind: Protein
Organism: Human
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]

Details11. Small conductance calcium-activated potassium channel protein 2

Kind: Protein
Organism: Human
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]

Details12. Small conductance calcium-activated potassium channel protein 3

Kind: Protein
Organism: Human
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]

Details13. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Human
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]

Details14. Potassium voltage-gated channel subfamily H member 6

Kind: Protein
Organism: Human
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]

Details15. Potassium voltage-gated channel subfamily H member 7

Kind: Protein
Organism: Human
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]

Details16. Nuclear receptor subfamily 1 group I member 2

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Partial agonist

General Function: Zinc ion binding
Specific Function: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name: NR1I2
Uniprot ID: O75469
Uniprot Name: Nuclear receptor subfamily 1 group I member 2
Molecular Weight: 49761.245 Da

References

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

Details1. Cytochrome P450 2A6

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. 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]

Details2. Cytochrome P450 2B6

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally 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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	6000	N/A	N/A	14761192

Details3. Cytochrome P450 2C9

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally 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]

Details4. Cytochrome P450 2C19

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and 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]

Details5. Cytochrome P450 2D6

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
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]

Details6. Cytochrome P450 2E1

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name: CYP2E1
Uniprot ID: P05181
Uniprot Name: Cytochrome P450 2E1
Molecular Weight: 56848.42 Da

References

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. [PubMed:9574817]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	180	N/A	N/A	12699389
IC 50 (nM)	8.51E+02	N/A	N/A	19128860

Details7. Cytochrome P450 3A4

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Substrate
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

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]

Details8. Cytochrome P450 11B1, mitochondrial

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid 11-beta-monooxygenase activity
Specific Function: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to 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]

Details9. Lanosterol 14-alpha demethylase

Kind: Protein
Organism: Human
Pharmacological action: Unknown

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]

Details10. Cytochrome P450 19A1

Kind: Protein
Organism: Human
Pharmacological action: Unknown

General Function: Oxygen binding
Specific Function: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name: CYP19A1
Uniprot ID: P11511
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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	2000	N/A	N/A	12699389
IC 50 (nM)	3500	N/A	N/A	12699389
Ki (nM)	26360	N/A	N/A	11961113
Ki (nM)	55500	N/A	N/A	11961113

Details1. Multidrug resistance protein 1

Kind: Protein
Organism: Human
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 November 18, 2018 13:32

Miconazole

Identification

Structure for Miconazole (DB01110)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

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Transporters

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