Miconazole

Summary

Miconazole (CHEMBL91) is an approved small molecule (ATC G01AF04) targeting CYP8B1, TRPM2, and TRPV5; indicated across 9 conditions including tinea infection and tinea pedis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: G01AF04 (+6 more)
• Targets: 3 (CYP8B1, TRPM2, TRPV5)
• Indications: 9 conditions
• Clinical trials: 12
• Chemistry: 416.1 Da · C18H14Cl4N2O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL91
Name	Miconazole
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4189
ChEBI	CHEBI:82892
ATC	G01AF04, S02AA13, J02AB01, A01AB09, D01AC52, A07AC01, D01AC02
Molecular formula	C18H14Cl4N2O
Molecular weight	416.1
InChIKey	BYBLEWFAAKGYCD-UHFFFAOYSA-N

SMILES: C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl

IUPAC name: 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole

ChEBI definition: A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.

Also known as: Conofite, Dumicoat, Dermazole, Loramyc, Miconazol, Miconazole, Monistat, Micatin, Monistat-3, NSC-170986, Oravig, Vusion

Parent form; salt/anhydrous children: CHEMBL1559, CHEMBL4578119

Patent coverage: 12,938 distinct patent families (45,914 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 45,401 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
CYP8B1	CYP8B1	Inhibition	6.34	0%	Q9UNU6
TRPM2	TRPM2	Antagonist		0.4%	O94759
TRPV5	TRPV5			0%	Q9NQA5

Broader ChEMBL bioactivity targets: 81 (assay-derived). Sample: Cytochrome P450 1A2, Indoleamine 2,3-dioxygenase 1, Nuclear receptor ROR-gamma, Prelamin-A/C, Cytochrome P450 1A2, Mycocyclosin synthase, Muscarinic acetylcholine receptor M4, Receptor tyrosine-protein kinase erbB-2, 5-hydroxytryptamine receptor 2B, Thromboxane-A synthase.

Bioactivity

ChEMBL activities: 124 potent at pChembl ≥ 5 of 164 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CYP2C19	10.7	IC50	0.02	nM	CHEMBL_ACT_24672707
CYP3A4	9	IC50	1	nM	CHEMBL_ACT_24672713
LMNA	8.05	Potency	8.9	nM	CHEMBL_ACT_3644899
CYP2C19	7.8	IC50	16	nM	CHEMBL_ACT_7754143
CYP2C19	7.6	Potency	25.1	nM	CHEMBL_ACT_4016227
CYP2C19	7.6	AC50	25.12	nM	CHEMBL_ACT_6017233
CYP3A4	7.52	IC50	30	nM	CHEMBL_ACT_25643679
CYP2C19	7.21	IC50	62	nM	CHEMBL_ACT_25643675
P9WPP7	7.14	Kd	73	nM	CHEMBL_ACT_16585275
CYP3A4	7.13	IC50	74.2	nM	CHEMBL_ACT_23308591
CYP3A4	7	IC50	100	nM	CHEMBL_ACT_7754151
CYP2C9	6.94	IC50	115	nM	CHEMBL_ACT_25643673
CYP3A4	6.75	IC50	180	nM	CHEMBL_ACT_1180564
CYP51A1	6.7	IC50	200	nM	CHEMBL_ACT_2122926
P9WPP9	6.7	Kd	200	nM	CHEMBL_ACT_5230882
CYP2C9	6.7	IC50	200	nM	CHEMBL_ACT_7754145
CYP17A1	6.61	Ki	243	nM	CHEMBL_ACT_1061063
TBXAS1	6.58	IC50	263	nM	CHEMBL_ACT_7756335
CYP2C9	6.5	Potency	316.2	nM	CHEMBL_ACT_5069426
CYP2C9	6.5	AC50	316.2	nM	CHEMBL_ACT_5996536
P22443	6.4	EC50	400	nM	CHEMBL_ACT_732047
SLC6A4	6.38	Ki	414	nM	CHEMBL_ACT_7756322
CHRM4	6.35	Ki	446	nM	CHEMBL_ACT_7756234
CYP3A4	6.3	Potency	501.2	nM	CHEMBL_ACT_5009968
CYP3A4	6.3	Potency	501.2	nM	CHEMBL_ACT_5074635
CYP3A4	6.3	AC50	501.2	nM	CHEMBL_ACT_6014011
CYP2J2	6.24	IC50	580	nM	CHEMBL_ACT_15445913
CYP19A1	6.22	IC50	600	nM	CHEMBL_ACT_3290699
CYP2J2	6.19	IC50	640	nM	CHEMBL_ACT_15445912
CHRM3	6.17	Ki	668	nM	CHEMBL_ACT_7756232

Target pathways

Aggregated over 3 target gene(s): CYP8B1, TRPM2, TRPV5.

Top Reactome pathways

8 total, by targets touching each:

Pathway	Targets	Genes
TRP channels	2	TRPM2, TRPV5
Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol	1	CYP8B1
Synthesis of bile acids and bile salts via 24-hydroxycholesterol	1	CYP8B1
Synthesis of bile acids and bile salts via 27-hydroxycholesterol	1	CYP8B1
Eicosanoids	1	CYP8B1
Sterols are 12-hydroxylated by CYP8B1	1	CYP8B1
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)	1	CYP8B1
Neutrophil degranulation	1	TRPM2

Dominant GO biological processes

GO term	Targets
calcium ion transport	2
protein homotetramerization	2
calcium ion transmembrane transport	2
calcium ion transmembrane import into cytosol	2
calcium ion import across plasma membrane	2
monoatomic ion transport	2
monoatomic ion transmembrane transport	2
transmembrane transport	2
steroid biosynthetic process	1
bile acid biosynthetic process	1
sterol metabolic process	1
response to nutrient levels	1
positive regulation of intestinal cholesterol absorption	1
response to cholesterol	1
lipid metabolic process	1

Indications & clinical

Indications

9 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
tinea infection	4	MONDO:0005982	EFO:0007510
tinea pedis	4	MONDO:0005984	EFO:0007512
fungal infectious disease	4	MONDO:0002041	MONDO:0002041
HIV infectious disease	3	MONDO:0005109	EFO:0000764
otomycosis	3	MONDO:0000262	MONDO:0000262
stomatitis	2	MONDO:0004842	EFO:1001904
intertrigo	0	MONDO:0021340	MONDO:0021340

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 12.

Phase distribution

Phase	Trials
PHASE4	3
PHASE3	3
PHASE2	2
PHASE1	2
PHASE2/PHASE3	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00194324	PHASE4	COMPLETED	Effect of Exercise on Spread of the Miconozole Nitrate OVULE in the Vagina
NCT01661556	PHASE4	UNKNOWN	Clinical Trial of Hydroquinone Versus Miconazol in Melasma
NCT05916729	PHASE4	UNKNOWN	Use of Maqui Berry Extract in Treating Oral Candidiasis in Diabetes Mellitus Patients and Systemically Healthy Persons
NCT00390780	PHASE3	COMPLETED	Efficacy and Safety Study of Miconazole Lauriad to Treat Oropharyngeal Candidiasis in HIV Patients
NCT02818803	PHASE3	COMPLETED	Efficacy of Standardized-propolis Extract (EPP-AF®) Gel Formulation as Buccal Antiseptic
NCT04432376	PHASE2/PHASE3	COMPLETED	Efficacy and Safety Study of Miconazole Oil Versus Vehicle on Fungal Infection of the Ear Canal (Otomycosis)
NCT05660382	PHASE3	COMPLETED	Phase III Efficacy and Safety Study of Miconazole Oil for Otomycosis
NCT03359070	PHASE2	COMPLETED	Clinical Trial Comparing Dapaconazole Versus Miconazole in Patients With Tinea Cruris
NCT04813822	PHASE2	UNKNOWN	Study Evaluating the Efficacy and Safety of Miconazole Nitrate + Domiphen Bromide Vaginal Cream in the Treatment of Subjects With Acute Vulvovaginal Candidiasis
NCT00004575	PHASE1	COMPLETED	Effects of Miconazole on Blood Flow
NCT01731574	PHASE1	COMPLETED	DDI Potential: Dapivirine Vaginal Ring and Miconazole Nitrate
NCT01118910	EARLY_PHASE1	COMPLETED	Open-Label Pilot Study of the Efficacy and Safety of Vusion Ointment for the Treatment of Intertrigo

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

12 molecules share ≥1 primary target. Top 12 by shared-target count:

Molecule	Source	Status	Shared targets
CLOTRIMAZOLE	ChEMBL + PubChem	Phase 4 (approved)	CYP8B1, TRPM2
ECONAZOLE	ChEMBL + PubChem	Phase 4 (approved)	CYP8B1, TRPM2
ADENOSINE	ChEMBL + PubChem	Phase 4 (approved)	TRPM2
COPPER	ChEMBL	Phase 4 (approved)	TRPM2
ITRACONAZOLE	ChEMBL	Phase 4 (approved)	CYP8B1
KETOCONAZOLE	ChEMBL	Phase 4 (approved)	CYP8B1
POSACONAZOLE	ChEMBL	Phase 4 (approved)	CYP8B1
TRANYLCYPROMINE	ChEMBL	Phase 4 (approved)	CYP8B1
FLUFENAMIC ACID	ChEMBL	Phase 2	TRPM2
TETRAHYDROCANNABIVARIN	ChEMBL	Phase 2	TRPV5
Mefenamic Acid	PubChem	Approved	TRPM2
Nadide	PubChem	Approved	TRPM2