U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H14Cl4N2O
Molecular Weight 416.129
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICONAZOLE

SMILES

ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

InChI

InChIKey=BYBLEWFAAKGYCD-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H14Cl4N2O
Molecular Weight 416.129
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Miconazole is a synthetic imidazole derivative, a topical antifungal agent for use in the local treatment of vaginal, and skin and nail infections due to yeasts and dermatophytes. It is particularly active against Candida spp., Trichophyton spp., Epidermophyton spp., Microsporum spp. and Pityrosporon orbiculare (Malassezia furfur), but also possesses some activity against Gram-positive bacteria. It binds to the heme moiety of the fungal cytochrome P-450 dependent enzyme lanosterol 14-alpha-demethlyase. Inhibits 14-alpha-demethlyase, blocks formation of ergosterol and leads to the buildup of toxic methylated 14-a-sterols. Miconazole also affects the synthesis of triglycerides and fatty acids and inhibits oxidative and peroxidative enzymes, increasing the amount of active oxygen species within the cell.

CNS Activity

Curator's Comment: Miconazole is brain penetrant in humans. In addition intracerebroventricular miconazole is CNS active in animals.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ORAVIG

Approved Use

ORAVIG is an azole antifungal indicated for the local treatment of oropharyngeal candidiasis in adults

Launch Date

1973
Curative
MONISTAT 1 COMBINATION PACK

Approved Use

Used to treats vaginal yeast infections, relieves external itching and irritation due to a vaginal yeast infection

Launch Date

2001
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
39.1 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MICONAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
136.1 μg × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MICONAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.5 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MICONAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1200 mg single, vaginal
Recommended
Dose: 1200 mg
Route: vaginal
Route: single
Dose: 1200 mg
Sources:
unhealthy, 18 - 60 years
n = 50
Health Status: unhealthy
Condition: vaginal candidosis
Age Group: 18 - 60 years
Sex: F
Population Size: 50
Sources:
200 mg 1 times / day multiple, intravenous
Dose: 200 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg, 1 times / day
Co-administed with::
amphotericin B
itraconazole
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Fibrillation ventricular...
AEs leading to
discontinuation/dose reduction:
Fibrillation ventricular (grade 5, 11.1%)
Sources:
800 mg single, intravenous
Dose: 800 mg
Route: intravenous
Route: single
Dose: 800 mg
Co-administed with::
amphotericin B
itraconazole
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Bradyarrhythmia...
AEs leading to
discontinuation/dose reduction:
Bradyarrhythmia (5.2%)
Sources:
0.25 % 7 times / day steady, topical
Recommended
Dose: 0.25 %, 7 times / day
Route: topical
Route: steady
Dose: 0.25 %, 7 times / day
Sources:
unhealthy, newborns
n = 330
Health Status: unhealthy
Condition: Diaper dermatitis complicated by candidiasis
Age Group: newborns
Sex: M+F
Population Size: 330
Sources:
AEs

AEs

AESignificanceDosePopulation
Fibrillation ventricular grade 5, 11.1%
Disc. AE
200 mg 1 times / day multiple, intravenous
Dose: 200 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg, 1 times / day
Co-administed with::
amphotericin B
itraconazole
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Bradyarrhythmia 5.2%
Disc. AE
800 mg single, intravenous
Dose: 800 mg
Route: intravenous
Route: single
Dose: 800 mg
Co-administed with::
amphotericin B
itraconazole
Sources:
unhealthy, 54 years
n = 1
Health Status: unhealthy
Age Group: 54 years
Sex: M
Population Size: 1
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Gold(I) complexes as antimicrobial agents.
1999 Apr 30
Differential inhibitory effects of protoberberines on sterol and chitin biosyntheses in Candida albicans.
1999 May
Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs.
2001 Aug
Primary culture system of adrenocortical cells from dogs to evaluate direct effects of chemicals on steroidogenesis.
2001 Aug 28
Effect of estrogen on flow-induced dilation in NO deficiency: role of prostaglandins and EDHF.
2001 Dec
Characterization of glassy itraconazole: a comparative study of its molecular mobility below T(g) with that of structural analogues using MTDSC.
2001 Feb 1
Regulation of phosphatidylserine transbilayer redistribution by store-operated Ca2+ entry: role of actin cytoskeleton.
2001 Feb 16
Reduced glutathione, dithiothreitol and cytochrome P-450 inhibitors do not influence hypoxic chemosensory responses in the rat carotid body.
2001 Jan 19
In vitro comparison of the antimycotic activity of a miconazole-HP-beta-cyclodextrin solution with a miconazole surfactant solution.
2001 Jul
Miconazole-warfarin interaction: increased INR.
2001 Jul 10
Exogenous endophthalmitis caused by amphotericin B-resistant Paecilomyces lilacinus: treatment options and visual outcomes.
2001 Jun
Progestins block cholesterol synthesis to produce meiosis-activating sterols.
2001 Mar
Lipid-based antifungal agents: current status.
2001 Mar
Case report. Cryptococcal cellulitis showing necrotizing vasculitis.
2001 May
Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin.
2001 May-Jun
Effects of azoles on human acute myelogenous leukemia blasts and T lymphocytes derived from acute leukemia patients with chemotherapy-induced cytopenia.
2001 Nov
Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.
2001 Nov
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.
2001 Oct
Androgen metabolism in oyster Crassostrea gigas: evidence for 17beta-HSD activities and characterization of an aromatase-like activity inhibited by pharmacological compounds and a marine pollutant.
2001 Oct
Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.
2001 Oct
[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use].
2001 Oct-Dec
Candida keratitis in a patient with candidiasis of the fingernails.
2001 Oct-Dec
Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles.
2001 Sep
7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures.
2001 Sep
Role of endothelium in hyperemia during cortical spreading depression (CSD) in the rat.
2002 Feb 22
Comparative study of the enantiomeric resolution of chiral antifungal drugs econazole, miconazole and sulconazole by HPLC on various cellulose chiral columns in normal phase mode.
2002 Jan 15
Fungal keratitis caused by Scedosporium apiospermum: report of two cases and review of treatment.
2002 Jul
Severe keratomycosis secondary to Scedosporium apiospermum.
2002 Jul
Inhibition of sarcoplasmic reticulum Ca2+-ATPase by miconazole.
2002 Jul
Overanticoagulation associated with combined use of antifungal agents and coumarin anticoagulants.
2002 Jun
7-Benzyloxyquinoline oxidation by P450eryF A245T: finding of a new fluorescent substrate probe.
2002 Jun
Inhibition of cytochromes P450 by antifungal imidazole derivatives.
2002 Mar
[A case of abrupt pulmonary infection by Rhizopus microsporus var. rhizopodiformis during treatment for bronchial asthma].
2002 May
Patents

Sample Use Guides

Application of one ORAVIG 50 mg buccal tablet to the gum region once daily for 14 consecutive days. External miconazole nitrate vulvar cream (2%): twice daily, for up to 7 days as needed. Miconazole nitrate vaginal insert (1200mg): with the applicator place the vaginal insert into the vagina.
Route of Administration: Other
The antifungal drug, miconazole nitrate, inhibits the growth of several species of Candida. Candida albicans, one of the pathogenic species, was totally inhibited at a concentration of approximately 10 mug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:12 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:12 GMT 2023
Record UNII
7NNO0D7S5M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MICONAZOLE
EP   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
Miconazole [WHO-DD]
Common Name English
(±)-1-(2,4-DICHLORO-B-((2,4-DICHLOROBENZYL)OXY)PHENETHYL)IMIDAZOLE
Common Name English
MICONAZOLE [JAN]
Common Name English
MICONAZOLE [VANDF]
Common Name English
1H-IMIDAZOLE, 1-2-((2,4-DICHLOROPHENYL)-2-((2,4-DICHLOROPHENYL))METHOXY)ETHYL)-, (±)-
Common Name English
miconazole [INN]
Common Name English
MICONAZOLE [USP IMPURITY]
Common Name English
MICONAZOLE [MART.]
Common Name English
MICONAZOLE [USP MONOGRAPH]
Common Name English
MICONAZOLE [EP IMPURITY]
Common Name English
MICONAZOLE [ORANGE BOOK]
Common Name English
MICONAZOLE [EP MONOGRAPH]
Common Name English
MICONAZOLE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QD01AC02
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC J02AB01
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC G01AF04
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
NDF-RT N0000008217
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-VATC QA01AB09
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
CFR 21 CFR 524.1445
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-VATC QA07AC01
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
FDA ORPHAN DRUG 406413
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
NDF-RT N0000175487
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC S02AA13
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC D01AC02
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
CFR 21 CFR 524.1443
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC A01AB09
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-VATC QS02AA13
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-VATC QG01AF04
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-VATC QD01AC52
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC D01AC52
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ATC A07AC01
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 13.1
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
WHO-VATC QJ02AB01
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
CFR 21 CFR 524.1132
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
245-324-5
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
PUBCHEM
4189
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
CAS
22916-47-8
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
INN
2728
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID6023319
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
NCI_THESAURUS
C62048
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
DAILYMED
7NNO0D7S5M
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
DRUG CENTRAL
1800
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
SMS_ID
100000090369
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
EVMPD
SUB08944MIG
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
RXCUI
6932
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY RxNorm
MESH
D008825
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
CHEBI
6923
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
WIKIPEDIA
MICONAZOLE
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
LACTMED
Miconazole
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
FDA UNII
7NNO0D7S5M
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
DRUG BANK
DB01110
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL91
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
MERCK INDEX
m7527
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY Merck Index
IUPHAR
2449
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
RS_ITEM_NUM
1443409
Created by admin on Fri Dec 15 15:10:12 GMT 2023 , Edited by admin on Fri Dec 15 15:10:12 GMT 2023
PRIMARY
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