Compound Detail

CHEMBL91

MICONAZOLE

💊 Approved Drug

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💊 Approved Drug

Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL91
Name	MICONAZOLE
Phase	Approved
Structure Type	MOL
InChI Key	BYBLEWFAAKGYCD-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Conofite Dermazole Dumicoat Loramyc Micatin Miconazol Miconazole Monistat Monistat-3 NSC-170986 Oravig Vusion

Targets

210

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

416.1

MW (Da)

6.45

ALogP

HBA

HBD

27.1

PSA (Å²)

0.46

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1974
Availability	OTC
Chirality	Racemic

Routes of Administration

Parenteral Topical

Flags

Natural Product

USAN Stem	-conazole
USAN Year	1970

Extended Properties

Molecular Formula	C18H14Cl4N2O
MW	416.13
Aromatic Rings	3
Heavy Atoms	25
NP-Likeness	-0.92

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cytochrome P450 51 inhibitor	INHIBITOR	Lanosterol 14-alpha demethylase	✓	✓

Indications

Infections Mycoses Pruritus Tinea Tinea Pedis HIV Infections Otomycosis Stomatitis Intertrigo

ATC Classification

A01AB09

miconazole

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: STOMATOLOGICAL PREPARATIONS

A07AC01

miconazole

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS

D01AC02

miconazole

Level 1: DERMATOLOGICALS

Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE

D01AC52

miconazole, combinations

Level 1: DERMATOLOGICALS

Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE

G01AF04

miconazole

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS

J02AB01

miconazole

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIMYCOTICS FOR SYSTEMIC USE

S02AA13

miconazole

Level 1: SENSORY ORGANS

Level 2: OTOLOGICALS

Activity Summary

IC50 155 meas. best 10.7

Ki 48 meas. best 6.61

Kd 6 meas. best 7.14

EC50 1 meas. best 6.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 2C19 CHEMBL3622	IC50	10.7	7.042	0.0	5
Unchecked CHEMBL612545	IC50	10.7	5.9415	0.0	20
Cytochrome P450 3A4 CHEMBL340	IC50	9.0	6.4309	1.0	11
Plasmodium yoelii yoelii CHEMBL612328	IC50	8.69	8.69	2.0	1
Kluyveromyces marxianus CHEMBL612842	IC50	7.52	7.52	30.0	1
Trypanosoma cruzi CHEMBL368	IC50	7.4	7.4	40.0	1
Mycocyclosin synthase CHEMBL1681615	Kd	7.14	7.14	73.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	6.94	6.02	115.0	3
Nakaseomyces glabratus CHEMBL612647	IC50	6.92	6.92	120.0	1
Trichophyton rubrum CHEMBL612649	IC50	6.85	6.665	140.0	2
Plasmodium falciparum CHEMBL364	IC50	6.7	6.57	200.0	3
Lanosterol 14-alpha demethylase CHEMBL3849	IC50	6.7	6.7	200.0	1
Sterol 14alpha-demethylase CHEMBL5090	Kd	6.7	6.7	200.0	1
Microsporum canis CHEMBL612335	IC50	6.64	6.64	230.0	1
Steroid 17-alpha-hydroxylase/17,20 lyase CHEMBL3522	Ki	6.61	6.61	243.0	1
Thromboxane-A synthase CHEMBL1835	IC50	6.58	6.58	263.0	1
Candida albicans CHEMBL366	IC50	6.52	5.825	300.0	4
Aromatase CHEMBL3859	EC50	6.4	6.4	400.0	1
Trichophyton mentagrophytes CHEMBL613162	IC50	6.4	6.4	400.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.38	6.38	414.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.35	6.35	446.0	1
Cytochrome P450 2J2 CHEMBL3491	IC50	6.24	6.215	580.0	2
Aromatase CHEMBL1978	IC50	6.22	6.22	600.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.17	6.17	668.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.11	6.11	778.0	1
HL-60 CHEMBL383	IC50	6.1	6.1	800.0	1
Trichophyton quinckeanum CHEMBL612334	IC50	6.1	6.1	790.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.06	5.95	875.0	3
Unchecked CHEMBL612545	Kd	6.03	5.7075	940.0	4
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.02	6.02	956.0	1
D(3) dopamine receptor CHEMBL234	Ki	5.96	5.96	1086.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.95	5.95	1116.0	1
Delta-type opioid receptor CHEMBL236	Ki	5.92	5.92	1194.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.87	5.87	1352.0	1
Indoleamine 2,3-dioxygenase 1 CHEMBL4685	IC50	5.85	5.495	1400.0	4
Pichia kudriavzevii CHEMBL612841	IC50	5.85	5.85	1400.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.83	5.83	1487.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	5.83	5.83	1497.0	1
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase CHEMBL4523494	IC50	5.82	5.82	1500.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	5.81	5.81	1542.0	1
Adenosine receptor A3 CHEMBL256	Ki	5.8	5.8	1589.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.79	5.79	1642.0	1
Substance-K receptor CHEMBL2327	Ki	5.79	5.79	1613.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.77	5.77	1701.0	1
Aspergillus fumigatus CHEMBL363	IC50	5.72	5.72	1900.0	1
Progesterone receptor CHEMBL1909044	Ki	5.71	5.71	1945.0	1
ATP-dependent translocase ABCB1 CHEMBL3467	IC50	5.7	5.7	2000.0	2
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.7	5.54	2000.0	3
Unchecked CHEMBL612545	Ki	5.69	5.372	2034.0	5
Acetylcholinesterase CHEMBL4078	IC50	5.62	5.145	2400.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	660.1	mL.min-1.kg-1	Mus musculus
CL	660.0	mL.min-1.g-1	Mus musculus
T1/2	0.1383	hr	Mus musculus
T1/2	0.1383	hr	Mus musculus
T1/2	0.011	hr	Mus musculus
T1/2	6.0	hr	Mus musculus
T1/2	0.1383	hr	Mus musculus
T1/2	6.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 2C19	IC50	=	0.02	nM	10.7	Inhibition of CYP2C19 in human liver Microsome using omeprazole as substrate in ...	36367749
Unchecked	IC50	=	0.02	nM	10.7	Inhibition of CYP2C19 in rat liver Microsome using phenacetin as substrate in pr...	36367749
Unchecked	IC50	=	0.02	nM	10.7	Inhibition of CYP2C19 in mouse liver Microsome using phenacetin as substrate in ...	36367749
Cytochrome P450 3A4	IC50	=	1.0	nM	9.0	Inhibition of CYP3A4 in human liver Microsome using midazolam as substrate in pr...	36367749
Unchecked	IC50	=	1.0	nM	9.0	Inhibition of CYP3A4 in rat liver Microsome using phenacetin as substrate in pre...	36367749
Unchecked	IC50	=	1.0	nM	9.0	Inhibition of CYP3A4 in mouse liver Microsome using phenacetin as substrate in p...	36367749
Plasmodium yoelii yoelii	IC50	=	2.03	nM	8.69	Antimicrobial activity against Plasmodium yoelii 265 liver infected in mammalian...	18212104
Cytochrome P450 2C19	IC50	=	16.0	nM	7.8	DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
Kluyveromyces marxianus	IC50	=	30.0	nM	7.52	Antifungal activity against 5 x 10'6 CFU/ml Candida kefyr B46120 by resazurin ba...	20805398
Cytochrome P450 3A4	IC50	=	30.0	nM	7.52	Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate prei...	37725043
Trypanosoma cruzi	IC50	=	40.0	nM	7.4	DNDI: Chagas in Vitro, 96 hour	-
Cytochrome P450 2C19	IC50	=	62.0	nM	7.21	Inhibition of CYP2C19 in human liver microsomes using diclofenac as substrate pr...	37725043
Mycocyclosin synthase	Kd	=	73.0	nM	7.14	Binding affinity to Mycobacterium tuberculosis H37Rv wild type CYP121 by titrati...	27002486
Cytochrome P450 3A4	IC50	=	74.2	nM	7.13	Inhibition of CYP3A4 in human liver microsome using Nifedipine as a substrate in...	34364163
Cytochrome P450 3A4	IC50	=	100.0	nM	7.0	DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluorome...	-
Cytochrome P450 2C9	IC50	=	115.0	nM	6.94	Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre...	37725043
Nakaseomyces glabratus	IC50	=	120.0	nM	6.92	Antifungal activity against 5 x 10'6 CFU/ml Candida glabrata B63155 by resazurin...	20805398
Trichophyton rubrum	IC50	=	140.0	nM	6.85	Antifungal activity against 5 x 10'6 CFU/ml Trichophyton rubrum J941704 by resaz...	20805398
Cytochrome P450 3A4	IC50	=	180.0	nM	6.75	Inhibition of human cytochrome P450 3A4	12699389
Plasmodium falciparum	IC50	=	200.0	nM	6.7	Antimalarial activity against chloroquine sensitive Plasmodium falciparum	33479627

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	725
357722	10.1021/jm00206a028	Candida albicans	26
29475581	10.1016/j.bmc.2018.02.014	Mus musculus	23
32403018	10.1016/j.ejmech.2020.112360	Unchecked	22
31191871	10.1039/C9MD00155G	Candida albicans	20
33713977	10.1016/j.ejmech.2021.113337	Lanosterol 14-alpha demethylase	20
29602683	10.1016/j.bmcl.2018.03.022	Candida albicans	19
27128176	10.1016/j.ejmech.2016.04.020	Candida albicans	19
26965863	10.1016/j.bmcl.2016.03.002	Candida albicans	18
27089214	10.1016/j.ejmech.2016.03.042	Candida albicans	18
26646219	10.1016/j.bmcl.2015.11.063	Candida albicans	18
26586599	10.1016/j.bmcl.2015.10.086	Candida albicans	17
33333162	10.1016/j.bmcl.2020.127746	Candida albicans	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
19015352	10.1128/aac.01095-08	Pichia kudriavzevii	13
33713977	10.1016/j.ejmech.2021.113337	Candida albicans	13
38116435	10.1021/acsmedchemlett.3c00406	Mycobacterium tuberculosis	11
27707604	10.1016/j.bmcl.2016.09.063	NON-PROTEIN TARGET	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
32403018	10.1016/j.ejmech.2020.112360	Candida albicans	11

Data from ChEMBL 36 via Core Engine