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Details

Stereochemistry RACEMIC
Molecular Formula C18H14Cl4N2O.HNO3
Molecular Weight 479.1418
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICONAZOLE NITRATE

SMILES

c1cc(cc(c1COC(Cn2ccnc2)c3ccc(cc3Cl)Cl)Cl)Cl.N(=O)(=O)O

InChI

InChIKey=MCCACAIVAXEFAL-UHFFFAOYSA-N
InChI=1S/C18H14Cl4N2O.HNO3/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;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula HNO3
Molecular Weight 63.0129
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Suppression of transient outward potassium currents in mouse ventricular myocytes by imidazole antimycotics and by glybenclamide.
2001 Aug
Increase of Candida cell virulence by anticancer drugs and irradiation.
2001 Aug
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
Efficacy of 7-day treatment with metronidazole+miconazole (Neo-Penotran) - a triple-active pessary for the treatment of single and mixed vaginal infections.
2001 Jul
In vitro comparison of the antimycotic activity of a miconazole-HP-beta-cyclodextrin solution with a miconazole surfactant solution.
2001 Jul
Endothelium-dependent desensitization to angiotensin II in rabbit aorta: the mechanisms involved.
2001 Jun
Exogenous endophthalmitis caused by amphotericin B-resistant Paecilomyces lilacinus: treatment options and visual outcomes.
2001 Jun
Molecular modeling study of beta- and gamma-cyclodextrin complexes with miconazole.
2001 Jun
A neuronal isoform of nitric oxide synthase expressed in pancreatic beta-cells controls insulin secretion.
2001 Jun
Characterization of endothelium-derived hyperpolarizing factor in the human forearm microcirculation.
2001 Jun
EDHF mediates flow-induced dilation in skeletal muscle arterioles of female eNOS-KO mice.
2001 Jun
Gender-specific compensation for the lack of NO in the mediation of flow-induced arteriolar dilation.
2001 Jun
Influence of the roll compactor parameter settings and the compression pressure on the buccal bio-adhesive tablet properties.
2001 Jun 4
Diaper dermatitis: a therapeutic dilemma. Results of a double-blind placebo controlled trial of miconazole nitrate 0.25%.
2001 Mar-Apr
Case report. Cryptococcal cellulitis showing necrotizing vasculitis.
2001 May
Comparison of in vitro activities of amphotericin, clotrimazole, econazole, miconazole, and nystatin against Fusarium oxysporum.
2001 May
Contact imidazole activity against resistant bacteria and fungi.
2001 May
Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions.
2001 May 15
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
Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates.
2001 Oct
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.
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
Reversal effects of antifungal drugs on multidrug resistance in MDR1-overexpressing HeLa cells.
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
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.
2002 Feb
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
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
Antifungal prophylaxis for severely neutropenic chemotherapy recipients: a meta analysis of randomized-controlled clinical trials.
2002 Jun 15
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
ABC transporters Cdr1p, Cdr2p and Cdr3p of a human pathogen Candida albicans are general phospholipid translocators.
2002 Mar 15
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 20:55:39 UTC 2021
Edited
by admin
on Fri Jun 25 20:55:39 UTC 2021
Record UNII
VW4H1CYW1K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MICONAZOLE NITRATE
EP   GREEN BOOK   INCI   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INCI   USAN  
Official Name English
M-ZOLE 7 DUAL PACK
Brand Name English
MICONAZOLE NITRATE [USP MONOGRAPH]
Common Name English
MONISTAT
Brand Name English
NSC-169434
Code English
MICONAZOLE NITRATE COMPONENT OF EASOTIC
Common Name English
MICONAZOLE NITRATE [USP-RS]
Common Name English
VUSION COMPONENT MICONAZOLE NITRATE
Common Name English
1H-IMIDAZOLE, 1-(2-(2,4-DICHLOROPHENYL)-2-((2,4-DICHLOROPHENYL)METHOXY)ETHYL)-, MONONITRATE
Systematic Name English
R 14,889
Code English
MICONAZOLE NITRATE [EMA EPAR: VETERINARY]
Common Name English
MICONAZOLE NITRATE [WHO-DD]
Common Name English
MICONAZOLE NITRATE [EP MONOGRAPH]
Common Name English
MICONAZOLE NITRATE [MART.]
Common Name English
EASOTIC COMPONENT MICONAZOLE NITRATE
Brand Name English
BAZA CREAM [VANDF]
Common Name English
MICONAZOLE NITRATE [INCI]
Common Name English
MICONAZOLE NITRATE COMPONENT OF VUSION
Common Name English
PRICONAZOLE
Common Name English
MICONAZOLE NITRATE [VANDF]
Common Name English
MICONAZOLE NITRATE [WHO-IP]
Common Name English
DERMONISTAT
Common Name English
MICONAZOLE NITRATE [JAN]
Common Name English
R-14889
Code English
1-(2,4-DICHLORO-.BETA.-((2,4-DICHLOROBENEZYL)OXY)PHENETHYL)IMIDAZOLE MONONITRATE
Common Name English
MICONAZOLE NITRATE [ORANGE BOOK]
Common Name English
M-ZOLE 3 COMBINATION PACK
Brand Name English
BAZA CREAM ANTIFUNGAL
Brand Name English
MICONAZOLE NITRATE [GREEN BOOK]
Common Name English
MICONAZOLE NITRATE [USAN]
Common Name English
MICONAZOLI NITRAS [WHO-IP LATIN]
Common Name English
MICONAZOLE NITRATE [MI]
Common Name English
Classification Tree Code System Code
EMA VETERINARY ASSESSMENT REPORTS EASOTIC (AUTHORISED)
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
CFR 21 CFR 333.210
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL91
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
CAS
22832-87-7
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
PUBCHEM
68553
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
RXCUI
42790
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY RxNorm
FDA UNII
VW4H1CYW1K
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
EVMPD
SUB03285MIG
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-256-6
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
MERCK INDEX
M7527
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C29257
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
DRUG BANK
DBSALT001242
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY
USP_CATALOG
1443500
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY USP-RS
WHO INTERNATIONAL PHARMACOPEIA
MICONAZOLE NITRATE
Created by admin on Fri Jun 25 20:55:39 UTC 2021 , Edited by admin on Fri Jun 25 20:55:39 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water and ether R; soluble in 140 parts of ethanol (~750 g/l) TS. Category: Antifungal drug. Storage: Miconazole nitrate should be kept in a well-closed container, protected from light. Additional information: Miconazole nitrate melts at about 182?C with decomposition. Definition: Miconazole nitrate contains not less than 98.5% and not more than 101.5% of C18H14Cl4N2O,HNO3, calculated with reference to the dried substance.
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY