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

c1cc(cc(c1COC(Cn2ccnc2)c3ccc(cc3Cl)Cl)Cl)Cl

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

126144000000
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

993686400000
Primary
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
Health Status: unhealthy
Age Group: 18 - 60 years
Sex: F
Sources:
200 mg 1 times / day multiple, intravenous
Dose: 200 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: M
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
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: M
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
Health Status: unhealthy
Age Group: newborns
Sex: M+F
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
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: M
Sources:
Bradyarrhythmia 5.2%
Disc. AE
800 mg single, intravenous
Dose: 800 mg
Route: intravenous
Route: single
Dose: 800 mg
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: M
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
Antifungal activity of a new triazole, voriconazole (UK-109496), against clinical isolates of Aspergillus spp.
2000 Jun
[Klion D - possibilities of prophylaxis and treatment during pregnancy].
2001
The importance of reassessment to chronic wound care.
2001 Aug
Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs.
2001 Aug
[Infection and colonization by Scedosporium prolificans].
2001 Aug-Sep
Anti-mycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis.
2001 Dec
Effect of estrogen on flow-induced dilation in NO deficiency: role of prostaglandins and EDHF.
2001 Dec
Chronic sino-naso-orbital fungal infection due to Pseudallescheria boydii in a nonimmunocompromised host--a case report.
2001 Jul
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
Initial and sustained phases of myogenic response of rat mesenteric small arteries.
2001 Nov
Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats.
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
Signaling pathway and chronotropic action of parathyroid hormone in isolated perfused rat heart.
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
7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures.
2001 Sep
Distribution and susceptibility of Candida species isolated in the Medical University of Debrecen.
2002
Routine versus selective antifungal administration for control of fungal infections in patients with cancer.
2002
Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis.
2002 Apr
N-methyl-D-aspartate-induced vasodilation is mediated by endothelium-independent nitric oxide release in piglets.
2002 Apr
Antitumor effects of miconazole on human colon carcinoma xenografts in nude mice through induction of apoptosis and G0/G1 cell cycle arrest.
2002 Apr 1
[Efficacy and tolerance of 200 mg of fenticonazole versus 400 mg of miconazole in the intravaginal treatment of mycotic vulvovaginitis].
2002 Feb
Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076.
2002 Feb
Use of cisapride with contraindicated drugs in The Netherlands.
2002 Feb
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.
2002 Feb
Sex-specific acute effect of estrogen on endothelium-derived contracting factor in the renal artery of hypertensive Dahl rats.
2002 Feb
Role of endothelium in hyperemia during cortical spreading depression (CSD) in the rat.
2002 Feb 22
Bioavailability study of a 1200 mg miconazole nitrate vaginal ovule in healthy female adults.
2002 Jan
Lontophoresis for the treatment of paecilomyces keratitis.
2002 Jan
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
Interaction between warfarin and topical miconazole cream.
2002 Jul 13
The opposite effects of cyclic AMP-protein kinase a signal transduction pathway on renal cortical and medullary Na+,K+-ATPase activity.
2002 Jun
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
Antifungal prophylaxis for severely neutropenic chemotherapy recipients: a meta analysis of randomized-controlled clinical trials.
2002 Jun 15
Rapid viability assessment of yeast cells using vital staining with 2-NBDG, a fluorescent derivative of glucose.
2002 Jun 5
Effect of direct infusion of antifungal agent on invasive pulmonary aspergillosis in a patient with acute leukemia.
2002 Mar
Comparison of dermatopharmacokinetic vs. clinicial efficacy methods for bioequivalence assessment of miconazole nitrate vaginal cream, 2% in humans.
2002 Mar
Effect of antifungal azoles on the heme detoxification system of malarial parasite.
2002 Mar
Inhibition of cytochromes P450 by antifungal imidazole derivatives.
2002 Mar
ABC transporters Cdr1p, Cdr2p and Cdr3p of a human pathogen Candida albicans are general phospholipid translocators.
2002 Mar 15
Enhancement of skin permeation of miconazole by phospholipid and dodecyl 2-(N,N-dimethyl amino)propionate (DDAIP).
2002 Mar 2
Pityriasis versicolor rubra.
2002 Mar-Apr
[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.
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 Jun 25 20:52:46 UTC 2021
Edited
by admin
on Fri Jun 25 20:52:46 UTC 2021
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 [EP]
Common Name English
(+/-)-1-(2,4-DICHLORO-B-((2,4-DICHLOROBENZYL)OXY)PHENETHYL)IMIDAZOLE
Common Name English
MICONAZOLE [JAN]
Common Name English
MICONAZOLE [USP]
Common Name English
MICONAZOLE [VANDF]
Common Name English
MICONAZOLE [WHO-DD]
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 [MART.]
Common Name English
MICONAZOLE [USP MONOGRAPH]
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 Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC J02AB01
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC G01AF04
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
NDF-RT N0000008217
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-VATC QA01AB09
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
CFR 21 CFR 524.1445
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-VATC QA07AC01
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
FDA ORPHAN DRUG 406413
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
NDF-RT N0000175487
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC S02AA13
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC D01AC02
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
CFR 21 CFR 524.1443
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC A01AB09
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-VATC QS02AA13
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-VATC QG01AF04
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-VATC QD01AC52
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC D01AC52
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ATC A07AC01
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 13.1
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
WHO-VATC QJ02AB01
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
CFR 21 CFR 524.1132
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
245-324-5
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
PUBCHEM
4189
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
CAS
22916-47-8
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
INN
2728
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
EPA CompTox
22916-47-8
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
NCI_THESAURUS
C62048
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
DRUG CENTRAL
1800
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
EVMPD
SUB08944MIG
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
RXCUI
6932
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY RxNorm
MESH
D008825
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
WIKIPEDIA
MICONAZOLE
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
LACTMED
Miconazole
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
FDA UNII
7NNO0D7S5M
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
DRUG BANK
DB01110
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL91
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
MERCK INDEX
M7527
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY Merck Index
IUPHAR
2449
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY
USP_CATALOG
1443409
Created by admin on Fri Jun 25 20:52:46 UTC 2021 , Edited by admin on Fri Jun 25 20:52:46 UTC 2021
PRIMARY USP-RS
Related Record Type Details
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
IC50
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY