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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Miconazole (DB01110)

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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

• Diaper Dermatitis
• Oropharyngeal Candidiasis
• Pityriasis versicolor
• Tinea Corporis
• Tinea Cruris
• Tinea Pedis
• Vaginal yeast infection
• Cutaneous candidiasis infection

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

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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

Target	Actions	Organism
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 C_max of 15.1 ± 16.2 mcg/mL, a mean AUC_0-24 of 55.2 ± 35.1 mcg*h/mL, and a median T_max 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 C_max of 10.71 ng/mL, mean T_max of 18.4 hours, and mean AUC_0-96 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.

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Unlock Additional Data
Abiraterone	The metabolism of Abiraterone can be decreased when combined with Miconazole.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Miconazole.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Miconazole.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Miconazole.
Acetaminophen	Miconazole may increase the hepatotoxic activities of Acetaminophen.
Acetohexamide	The serum concentration of Acetohexamide can be increased when it is combined with Miconazole.
Acetylsalicylic acid	The metabolism of Acetylsalicylic acid can be decreased when combined with Miconazole.
Albendazole	The metabolism of Albendazole can be decreased when combined with Miconazole.
Alectinib	The metabolism of Alectinib can be decreased when combined with Miconazole.
Alfuzosin	The 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

Ingredient	UNII	CAS	InChI Key
Miconazole nitrate	VW4H1CYW1K	22832-87-7	MCCACAIVAXEFAL-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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
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	Midatech Pharma Us, Inc.	2010-04-16	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

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
Miconazole Nitrate	Suppository	200 mg/1	Vaginal	Actavis Pharma, Inc.	1995-01-18	Not applicable

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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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
3M Cavilon Antifungal	Cream	2 g/1000g	Topical	3M Company	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
Anti-Fungal Buttery Balm Lady Bits	Ointment	2 g/100g	Topical	Derma Care Research Labs, LLC	2019-05-03	Not applicable
Antifungal	Cream	20 mg/1g	Topical	Cardinal Health	1991-10-01	Not applicable
Antifungal	Cream	20 mg/1g	Topical	PSS World Medical, Inc.	2012-09-05	Not applicable

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.
Learn more

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Antifungal Skin Care CVS	Miconazole nitrate (2 g/100mL) + Benzalkonium chloride (0.12 g/100mL)	Kit	Topical	Product Quest Mfg.	2016-04-14	2016-12-09
Basic Care miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	L. Perrigo Company	2017-08-29	Not applicable
Basic Care miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	L. Perrigo Company	2017-08-29	Not applicable
Care One Miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	American Sales Company	2010-11-19	Not applicable
Care One Miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	American Sales Company	2010-11-19	Not applicable
Care One Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	American Sales Company	2004-07-27	2014-10-16
Care One Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	American Sales Company	2004-07-27	2014-10-16
Careone Miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)		Topical; Vaginal	American Sales Company	2020-01-15	Not applicable
Careone Miconazole 1	Miconazole nitrate (1200 mg/1) + Miconazole nitrate (2 g/100g)		Topical; Vaginal	American Sales Company	2020-01-15	Not applicable
CareOne Miconazole 3	Miconazole nitrate (200 mg/1) + Miconazole nitrate (2 g/100g)	Kit	Topical; Vaginal	American Sales Company	2014-04-13	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Onycho-Med	Miconazole nitrate (200 mg/10mL) + Terbinafine hydrochloride (250 mg/250mg)	Kit	Topical	Medhart Pharmaceuticals, Inc.	2019-04-16	Not applicable

Categories

ATC Codes

A07AC01 — Miconazole

• A07AC — Imidazole derivatives
• A07A — INTESTINAL ANTIINFECTIVES
• A07 — ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
• A — ALIMENTARY TRACT AND METABOLISM

J02AB01 — Miconazole

• J02AB — Imidazole derivatives
• J02A — ANTIMYCOTICS FOR SYSTEMIC USE
• J02 — ANTIMYCOTICS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

D01AC52 — Miconazole, combinations

• D01AC — Imidazole and triazole derivatives
• D01A — ANTIFUNGALS FOR TOPICAL USE
• D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

G01AF20 — Combinations of imidazole derivatives

• G01AF — Imidazole derivatives
• G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
• G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

A01AB09 — Miconazole

• A01AB — Antiinfectives and antiseptics for local oral treatment
• A01A — STOMATOLOGICAL PREPARATIONS
• A01 — STOMATOLOGICAL PREPARATIONS
• A — ALIMENTARY TRACT AND METABOLISM

D01AC02 — Miconazole

• D01AC — Imidazole and triazole derivatives
• D01A — ANTIFUNGALS FOR TOPICAL USE
• D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

S02AA13 — Miconazole

• S02AA — Antiinfectives
• S02A — ANTIINFECTIVES
• S02 — OTOLOGICALS
• S — SENSORY ORGANS

G01AF04 — Miconazole

• G01AF — Imidazole derivatives
• G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
• G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
• G — GENITO URINARY SYSTEM AND SEX HORMONES

Drug Categories

• 14-alpha Demethylase Inhibitors
• Anti-Infective Agents
• Antifungal Agents
• Antifungal Agents (Vaginal)
• Antifungals for Dermatological Use
• Antifungals for Topical Use
• Antiinfectives and Antiseptics for Local Oral Treatment
• Azole Antifungals
• Chemically-Induced Disorders
• Cytochrome P-450 CYP2A6 Inhibitors
• Cytochrome P-450 CYP2A6 Inhibitors (strong)
• Cytochrome P-450 CYP2B6 Inhibitors
• Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Inhibitors (strong)
• Cytochrome P-450 CYP2C8 Inhibitors
• Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C9 Inhibitors
• Cytochrome P-450 CYP2C9 Inhibitors (moderate)
• Cytochrome P-450 CYP2C9 Inhibitors (strong)
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2E1 Inhibitors
• Cytochrome P-450 CYP2E1 Inhibitors (strong)
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (moderate)
• Cytochrome P-450 Enzyme Inhibitors
• Dermatologicals
• Enzyme Inhibitors
• Genito Urinary System and Sex Hormones
• Gynecological Antiinfectives and Antiseptics
• Hormone Antagonists
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Imidazole and Triazole Derivatives
• Imidazole Derivatives
• Imidazoles
• Intestinal Antiinfectives
• Otologicals
• P-glycoprotein inhibitors
• Sensory Organs
• Steroid Synthesis Inhibitors
• Stomatological Preparations
• Vaginal Creams, Foams, and Jellies

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Health / Vulvovaginal Candidiasis	1
4	Completed	Treatment	Diaper Rash	1
4	Completed	Treatment	Vulva; Candidiasis	1
4	Unknown Status	Treatment	Melasma	1
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
3	Completed	Treatment	Oral Candidiasis / Stomatitis, Denture	1
2	Completed	Prevention	Bacterial Vaginosis (BV) / Candidiasis / Trichomoniasis	1
2	Completed	Treatment	Otomycosis	1
2	Completed	Treatment	Tinea Cruris	1
2	Recruiting	Prevention	Oral Mucositis Due to Chemotherapy	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Actavis Group
• Advanced Pharmaceutical Services Inc.
• Barr Pharmaceuticals
• CVS Pharmacy
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Draxis Specialty Pharmaceuticals Inc.
• Ivax Pharmaceuticals
• Johnson & Johnson Healthcare
• Kaiser Foundation Hospital
• Medisca Inc.
• Ortho Mcneil Janssen Pharmaceutical Inc.
• Orthopedics Advanced Care
• Par Pharmaceuticals
• Perrigo Co.
• Pharmacia Inc.
• Pharmedix
• Physicians Total Care Inc.
• Prescript Pharmaceuticals
• Schering-Plough Inc.
• Southwood Pharmaceuticals

Dosage Forms

Form	Route	Strength
Ointment	Topical	20 mg/1g
Ointment	Topical	2.82 g/141g
Ointment	Topical	1.12 g/56g
Cream	Topical	2 mg/100mL
Cream	Topical	2 g/1000g
Cream	Topical	2.0 g/100mL
Spray	Topical	2 g/100g
Tincture	Topical	20 mg/1mL
Cream	Topical	0.02 g/1g
Cream	Topical	0.02 g/100g
Cream	Topical
Aerosol, powder	Topical	2 g/100g
Aerosol, spray	Topical	2 g/100g
Cream	Topical	2 g/100mL
Cream	Topical	2.0 g/100g
Ointment	Topical	2.0 g/100g
Powder	Topical	2 g/100mL
Kit	Topical	20 mg/1mL
Lotion	Topical	20 mg/1mL
Cream	Topical	20 mg/1mL
Aerosol, spray	Topical	0.2 g/10g
Cream	Topical	2 g/100g
Powder	Topical	1.42 g/71g
Aerosol, spray	Topical	20 mg/1g
Aerosol, powder	Topical	20 mg/1g
Liquid	Topical	2 g/100g
Spray	Topical	20 mg/1g
Cream	Topical
Aerosol	Topical
Powder	Not applicable	1 g/1g
Kit	Topical; Vaginal
Suppository	Vaginal
Cream	Vaginal	100 mg/1g
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	2 g/150g
Aerosol, spray	Topical	2.6 g/130g
Aerosol, spray	Topical	3 g/150g
Cream	Topical	100 mg/2mg
Cream	Vaginal	20 mg/1g
Powder	Topical	2.6 g/130g
Spray	Topical	3 g/150g
Suppository	Vaginal	100 ug/1
Aerosol, spray	Topical	1.3 g/131g
Powder	Topical	0.02 g/1g
Cream	Topical	0.3 g/14g
Capsule; cream; kit	Oral; Topical
Suppository	Vaginal	200 mg/1
Cream	Vaginal	40 mg/1g
Kit	Vaginal
Cream; insert	Topical; Vaginal
Insert	Vaginal
Cream; suppository	Topical; Vaginal
Cream	Vaginal
Cream	Topical	20 mg/1g
Cream	Topical	200 mg/1mg
Liquid	Topical	20 mg/1mg
Cream	Topical	.02 mL/1mL
Tablet	Buccal	50 mg/1
Cream	Topical	20 g/1000g
Liquid	Topical
Powder	Topical	2 g/100g
Powder	Topical	20 mg/1g
Ointment	Topical	2 g/100g
Cream	Topical	20 mg/100g
Kit	Topical
Cream	Topical	0.7 g/35g
Aerosol, powder	Topical	2.56 g/128g
Paste	Topical	2 g/100g
Cream	Vaginal	2 g/100g
Kit	Topical; Vaginal	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)	Region
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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

Additional Data Available

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

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	170	MSDS

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

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There is additional data available for commercial users including Adverse Effects, Contraindications, and Blackbox Warnings. Contact us to learn more about these and other features.

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Drug created on June 13, 2005 07:24 / Updated on August 02, 2020 22:18