MICONAZOLE

US Approved OTC

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 Search

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1149649 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf | http://www.antimicrobe.org/drugpopup/Miconazole.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 26 Target ID: CHEMBL1780 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf	Inhibitor 7701	Oropharyngeal candidiasis Vulvovaginal candidiasis
Sphingosine-1-phosphate lyase 1 3 Target ID: CHEMBL3286061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28930429	Inhibitor 7701	Multiple sclerosis

Conditions

Condition	Modality	Targets	Highest Phase	Product
Oropharyngeal candidiasis 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022404s003lbl.pdf	Curative	Cytochrome P450 51	Approved 7997	ORAVIG Approved Use ORAVIG is an azole antifungal indicated for the local treatment of oropharyngeal candidiasis in adults Launch Date 126144000000
Vulvovaginal candidiasis 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21308s009lbl.pdf	Curative	Cytochrome P450 51	Approved 7997	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
Multiple sclerosis 96 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25896324	Primary	Sphingosine-1-phosphate lyase 1	Preclinical

C_max

Value	Dose	Co-administered	Analyte	Population
39.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/	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

Value	Dose	Co-administered	Analyte	Population
136.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15373926/	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

Dose	Population	Adverse events
1200 mg single, vaginal Recommended Dose: 1200 mg Route: vaginal Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2270767/	unhealthy, 18 - 60 years Health Status: unhealthy Age Group: 18 - 60 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/2270767/	Sources: https://pubmed.ncbi.nlm.nih.gov/2270767/
200 mg 1 times / day multiple, intravenous Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	Disc. AE: Fibrillation ventricular... AEs leading to discontinuation/dose reduction: Fibrillation ventricular (grade 5, 11.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/
800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	Disc. AE: Bradyarrhythmia... AEs leading to discontinuation/dose reduction: Bradyarrhythmia (5.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/
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: https://pubmed.ncbi.nlm.nih.gov/16570675/	unhealthy, newborns Health Status: unhealthy Age Group: newborns Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16570675/	Sources: https://pubmed.ncbi.nlm.nih.gov/16570675/

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/
Bradyarrhythmia	5.2% Disc. AE	800 mg single, intravenous Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/	unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9085333/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1172	inhibitor 1318	inhibitor 1421	inhibitor 1360

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2A6 594 CYP2B6 679 CYP2C19 1215 CYP2E1 761 CYP3A4/5 225	P-gp 1223

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1462	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [IC50 0.175 uM]
CYP2C19 1277	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.01 uM]
CYP3A4/5 277	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.028 uM]
CYP2B6 845	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.05 uM]
CYP2D6 1455	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 0.7 uM]
CYP2C9 1362	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 1.2 uM]
CYP2A6 625	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 2.2 uM]
CYP1A2 1406	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 3.2 uM]
CYP2E1 841	inhibitor 2614 Sources: https://www.ingentaconnect.com/content/ben/cdm/2014/00000015/00000007/art00001 Page: -	yes [Ki 7.3 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1223	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/ Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1392	inhibitor 1374 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1576066/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO20569
1PlusChem LLC	1P002LXR
A2B Chem	AB20943
AA Blocks	AA002LEB
AK Scientific	I742
AK Scientific	J10381
AK Scientific	J10390
AK Scientific	W4662
APExBIO	B1977
APExBIO	B1978
AbovChem LLC	HY-B0454
AbovChem LLC	HY-B0454A
Achemo BB	AC-13879
Achemo BB	AC-76854
Ambeed	A209924
Angene	AGN-PC-0QZHGM
Apollo Scientific	BIM0132
AstaTech	35147
AstaTech	41284
BLDpharm	BD55353
BOC Sciences	22832-37-7
BOC Sciences	22832-87-7
BOC Sciences	22916-47-8
Bide Pharmatech	BD49689
Bide Pharmatech	BD55353
BlocksMatrix Scientific	90792
Bosche Scientific	M0037
Bosche Scientific	M6558
Cayman Chemical	15420
Chem Scene	CS-2565
Chem Scene	CS-2881
ChemShuttle	134701
ChemShuttle	151545
Combi-Blocks	QA-7241
Combi-Blocks	QB-6813
Compound Cloud	4189
Compound Cloud	68553
Debye Scientific	DB-046018
Fluorochem	361942
Fluorochem	397179
Hairui	HR124240
Hairui	HR135292
Hangzhou Yuhao Chemical Technology	LT7431
HongKong Chemhere	SCE30247
IBScreen	STOCK1S-93556
KeyOrganics	AS-13575
KeyOrganics	DS-1881
Lab Network	LN00188719
Lab Network	LN00239078
Lab Network	LN01754924
Lab Seeker	SC-19243
MedChem Express	HY-B0454
MedChem Express	HY-B0454A
MolPort	MolPort-000-710-887
MolPort	MolPort-002-557-553
MolPort	MolPort-003-665-537
Molcore	CS20569
Molnova	M13627
Molnova	M13636
MuseChem	A000799
MuseChem	R011652
NCI Plated 2007	169434
NCI Plated 2007	170986
Nanjing Pope Bio-tech	NSTH-D11455
Norris Pharm	NSTH-D11455
Oakwood	361942
PI Chemicals	PI-11488
Pharmeks	PHAR018263
Princeton BioMolecular Research	OSSL_856838
Princeton BioMolecular Research	OSSM_058449
Ryan Scientific	Fenspiride_HCl
Selleck Chemicals	S1956
Selleck Chemicals	S2536
ShangHai Biochempartner	BCP13696
Sigma Aldrich	1443500
Sigma Aldrich	1443500\|USP
Sigma Aldrich	BP253
Sigma Aldrich	M1900000
Sigma Aldrich	M1900000\|SIAL
Sigma Aldrich	M3512
Sigma Aldrich	M3512\|SIGMA
Sigma Aldrich	PHR1163
Sigma Aldrich	PHR1163\|SIAL
Specs	AE-641/01941016
StruChem	SC-19243
TargetMol	T0344
TargetMol	T0344L
TimTec	SBB057009
TimTec	SBB057453
TimTec	ST024747
TimTec	ST50983989
Tocris	3016
Toronto Research Chemicals	D292727
Toronto Research Chemicals	M342500
Vitas-M Laboratory	STK834405
ZINC	ZINC000000607971	http://zinc15.docking.org/substances/ZINC000000607971
ZINC	ZINC000000896740	http://zinc15.docking.org/substances/ZINC000000896740
eMolecules	299997579
eMolecules	313108266
eMolecules	591843
eMolecules	76739258
eMolecules	76739260
eMolecules	902133
eNovation Chemicals	D573728
eNovation Chemicals	D764340
mcule	MCULE-2106181573
mcule	MCULE-7996605731

PubMed

Title	Date	PubMed
Antifungal activity of a new triazole, voriconazole (UK-109496), against clinical isolates of Aspergillus spp.	2000 Jun	11810544
[Klion D - possibilities of prophylaxis and treatment during pregnancy].	2001	11803871
The importance of reassessment to chronic wound care.	2001 Aug	11889999
Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs.	2001 Aug	11569882
[Infection and colonization by Scedosporium prolificans].	2001 Aug-Sep	11747789
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	11886533
Effect of estrogen on flow-induced dilation in NO deficiency: role of prostaglandins and EDHF.	2001 Dec	11717219
Chronic sino-naso-orbital fungal infection due to Pseudallescheria boydii in a nonimmunocompromised host--a case report.	2001 Jul	12024935
Effects of azoles on human acute myelogenous leukemia blasts and T lymphocytes derived from acute leukemia patients with chemotherapy-induced cytopenia.	2001 Nov	11710547
Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.	2001 Nov	11682448
Initial and sustained phases of myogenic response of rat mesenteric small arteries.	2001 Nov	11668080
Chronic estrogen depletion alters adenosine diphosphate-induced pial arteriolar dilation in female rats.	2001 Nov	11668072
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.	2001 Oct	11744942
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	11717006
Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.	2001 Oct	11598232
Signaling pathway and chronotropic action of parathyroid hormone in isolated perfused rat heart.	2001 Oct	11588519
[Vaginal candidiasis: etiology and sensitivity profile to antifungal agents in clinical use].	2001 Oct-Dec	11833253
Candida keratitis in a patient with candidiasis of the fingernails.	2001 Oct-Dec	11820312
7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures.	2001 Sep	11524113
Distribution and susceptibility of Candida species isolated in the Medical University of Debrecen.	2002	12109169
Routine versus selective antifungal administration for control of fungal infections in patients with cancer.	2002	12076377
Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis.	2002 Apr	11914502
N-methyl-D-aspartate-induced vasodilation is mediated by endothelium-independent nitric oxide release in piglets.	2002 Apr	11893577
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	11922774
[Efficacy and tolerance of 200 mg of fenticonazole versus 400 mg of miconazole in the intravaginal treatment of mycotic vulvovaginitis].	2002 Feb	12017948
Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076.	2002 Feb	12002999
Use of cisapride with contraindicated drugs in The Netherlands.	2002 Feb	11847959
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.	2002 Feb	11834610
Sex-specific acute effect of estrogen on endothelium-derived contracting factor in the renal artery of hypertensive Dahl rats.	2002 Feb	11821708
Role of endothelium in hyperemia during cortical spreading depression (CSD) in the rat.	2002 Feb 22	11844470
Bioavailability study of a 1200 mg miconazole nitrate vaginal ovule in healthy female adults.	2002 Jan	11808824
Lontophoresis for the treatment of paecilomyces keratitis.	2002 Jan	11805526
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	11755745
Fungal keratitis caused by Scedosporium apiospermum: report of two cases and review of treatment.	2002 Jul	12072730
Severe keratomycosis secondary to Scedosporium apiospermum.	2002 Jul	12072729
Inhibition of sarcoplasmic reticulum Ca2+-ATPase by miconazole.	2002 Jul	12055076
Interaction between warfarin and topical miconazole cream.	2002 Jul 13	12114237
The opposite effects of cyclic AMP-protein kinase a signal transduction pathway on renal cortical and medullary Na+,K+-ATPase activity.	2002 Jun	12120897
Overanticoagulation associated with combined use of antifungal agents and coumarin anticoagulants.	2002 Jun	12087353
7-Benzyloxyquinoline oxidation by P450eryF A245T: finding of a new fluorescent substrate probe.	2002 Jun	12067248
Antifungal prophylaxis for severely neutropenic chemotherapy recipients: a meta analysis of randomized-controlled clinical trials.	2002 Jun 15	12115356
Rapid viability assessment of yeast cells using vital staining with 2-NBDG, a fluorescent derivative of glucose.	2002 Jun 5	12038577
Effect of direct infusion of antifungal agent on invasive pulmonary aspergillosis in a patient with acute leukemia.	2002 Mar	11957130
Comparison of dermatopharmacokinetic vs. clinicial efficacy methods for bioequivalence assessment of miconazole nitrate vaginal cream, 2% in humans.	2002 Mar	11934233
Effect of antifungal azoles on the heme detoxification system of malarial parasite.	2002 Mar	11872173
Inhibition of cytochromes P450 by antifungal imidazole derivatives.	2002 Mar	11854151
ABC transporters Cdr1p, Cdr2p and Cdr3p of a human pathogen Candida albicans are general phospholipid translocators.	2002 Mar 15	11870854
Enhancement of skin permeation of miconazole by phospholipid and dodecyl 2-(N,N-dimethyl amino)propionate (DDAIP).	2002 Mar 2	11839443
Pityriasis versicolor rubra.	2002 Mar-Apr	11872414
[A case of abrupt pulmonary infection by Rhizopus microsporus var. rhizopodiformis during treatment for bronchial asthma].	2002 May	12073577

Patents

Sample Use Guides

In Vivo Use Guide

Application of one ORAVIG 50 mg buccal tablet to the gum region once daily for 14 consecutive days.

Route of Administration: Other

In Vitro Use Guide

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

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Name

Type

Language

MICONAZOLE

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