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

Details

Stereochemistry RACEMIC
Molecular Formula C18H14Cl4N2O.HNO3
Molecular Weight 479.141
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICONAZOLE NITRATE

SMILES

O[N+]([O-])=O.ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C3=C(Cl)C=C(Cl)C=C3)C=C1

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 63.0128
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

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
Systemic Candida infection in University hospital 1997-1999: the distribution of Candida biotypes and antifungal susceptibility patterns.
2001
Spectrophotometric resolution of metronidazole and miconazole nitrate in ovules using ratio spectra derivative spectrophotometry and RP-LC.
2001 Apr
Flow-induced dilation of human coronary arterioles: important role of Ca(2+)-activated K(+) channels.
2001 Apr 17
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
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
[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
Possible role of nitric oxide and arachidonic acid pathways in hypoxia-induced contraction of rabbit coronary artery rings.
2001 Feb
[Tinea faciei in a newborn].
2001 Feb
Identification and expression of multidrug resistance-related ABC transporter genes in Candida krusei.
2001 Feb
Corneal co-infection with Scedosporium apiospermum and Acanthamoeba after sewage-contaminated ocular injury.
2001 Jan
Systemic antifungal agents.
2001 Jul
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
Gender-specific compensation for the lack of NO in the mediation of flow-induced arteriolar dilation.
2001 Jun
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.
2001 Jun 15
A novel bovine lactoferrin peptide, FKCRRWQWRM, suppresses Candida cell growth and activates neutrophils.
2001 Mar
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
HWY-289, a novel semi-synthetic protoberberine derivative with multiple target sites in Candida albicans.
2001 May
Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin.
2001 May-Jun
Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats.
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
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
Signaling pathway and chronotropic action of parathyroid hormone in isolated perfused rat heart.
2001 Oct
Involvement of cytochrome P450 metabolites in the vascular action of angiotensin II on the afferent arterioles.
2001 Sep
The role of endothelium-derived hyperpolarizing factor in the regulation of the uterine circulation in pregnant rats.
2001 Sep
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
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
Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076.
2002 Feb
Bioavailability study of a 1200 mg miconazole nitrate vaginal ovule in healthy female adults.
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
Severe keratomycosis secondary to Scedosporium apiospermum.
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 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
Pityriasis versicolor rubra.
2002 Mar-Apr
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 15:10:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:10 GMT 2023
Record UNII
VW4H1CYW1K
Record Status Validated (UNII)
Record Version
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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 [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
Miconazole nitrate [WHO-DD]
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 Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
CFR 21 CFR 333.210
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID50996767
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL91
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
NSC
169434
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
CAS
22832-87-7
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
PUBCHEM
68553
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
RXCUI
42790
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY RxNorm
RS_ITEM_NUM
1443500
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
FDA UNII
VW4H1CYW1K
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
EVMPD
SUB03285MIG
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-256-6
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
MERCK INDEX
m7527
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C29257
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
DRUG BANK
DBSALT001242
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
MICONAZOLE NITRATE
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
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.
DAILYMED
VW4H1CYW1K
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
SMS_ID
100000091859
Created by admin on Fri Dec 15 15:10:11 GMT 2023 , Edited by admin on Fri Dec 15 15:10:11 GMT 2023
PRIMARY
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