ContaminantDB: Miconazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (17)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:24 UTC

Update Date

2026-03-26 22:25:27 UTC

Accession Number

CHEM002349

Identification

Common Name

Miconazole

Class

Small Molecule

Description

Miconazole is only found in individuals that have used or taken this drug. It is an imidazole antifungal agent that is used topically and by intravenous infusion. [PubChem] Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

14-alpha Demethylase Inhibitor
Amine
Antifungal Agent
Drug
Ether
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Monistat	Kegg
Oravig	Kegg
MCZ	HMDB
Dactarin	HMDB
Esteve brand OF miconazole	HMDB
Janssen-cilag brand OF miconazole	HMDB
Miconazole nitrate	HMDB
Johnston and johnston brand OF miconazole nitrate	HMDB
Miconazole esteve brand	HMDB
Janssen cilag brand OF miconazole	HMDB
Brentan	HMDB
Miconasil nitrate	HMDB
Miconazole janssen-cilag brand	HMDB
Nitrate, miconasil	HMDB
Nitrate, miconazole	HMDB
Miconazole	MeSH

Chemical Formula

C₁₈H₁₄Cl₄N₂O

Average Molecular Mass

416.129 g/mol

Monoisotopic Mass

413.986 g/mol

CAS Registry Number

22916-47-8

IUPAC Name

1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

Traditional Name

miconazole

SMILES

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

InChI Identifier

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

InChI Key

BYBLEWFAAKGYCD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Imidazole
Azole
Heteroaromatic compound
Ether
Dialkyl ether
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:82892 )
ether (CHEBI:82892 )
dichlorobenzene (CHEBI:82892 )
a small molecule (CPD-4501 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antifungal agent

Biological Roles

antifungal agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	159-163°C
Boiling Point	Not Available
Solubility	1g/100mL (20°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.00076 g/L	ALOGPS
logP	5.86	ALOGPS
logP	5.96	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.07 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9233000000-cf671d00eb6cf2e83a70	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-02t9-0501900000-40f5928152d84e02deef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-015c-4900000000-628ede89a2ff3a714388	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-02t9-0501900000-40f5928152d84e02deef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0bt9-2900000000-1921b08c2de7bbf0624d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0bt9-0900500000-1a5805da9606edbe7e9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0bt9-0900500000-c890bda85d3a2b7105a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014r-0900000000-190edb871f246002e528	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0900000000-205437c234d274556334	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-88ad1ad97a03f81cb62b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-47bdad19f51fe408503d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0010900000-fdb45193fda5b55b51fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-029i-8196600000-0688ca27d69a2b799e4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9231000000-36d36a480a365220e479	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1001900000-6bf34660d27cb9682f77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9001100000-646beb070226cf30103f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9200000000-cddc446725179619915f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-0d807dba101c997f9733	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1311900000-70dc1f7ee3a9b86b7cc1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9730000000-751a82e89fec83a5cf3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1190300000-1eb2f0eb6c1eb7c48f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9200000000-39ed9c2c276ae71cec93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-9110000000-449b67e2d6c705113bcd	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0bt9-4900000000-3f143064c2acde7e15a4	Spectrum

Toxicity Profile

Route of Exposure

Topical

Mechanism of Toxicity

Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Metabolism

Not Available

Toxicity Values

LD50: 3800 mg/kg (Oral, Mouse) (1) LD50: 3 gm/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID