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Compound Detail

CHEMBL808

ECONAZOLE
💊 Approved Drug
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💊 Approved Drug
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1

Basic Information

ChEMBL ID CHEMBL808
Name ECONAZOLE
Phase Approved
Structure Type MOL
InChI Key LEZWWPYKPKIXLL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Econazol Econazole NSC-187789
74
Targets
137
Activities
3
Assay Types
2
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

381.7
MW (Da)
5.80
ALogP
3
HBA
0
HBD
27.1
PSA (Ų)
0.54
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Racemic

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -conazole
USAN Year 1972

Extended Properties

Molecular Formula C18H15Cl3N2O
MW 381.69
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.92

Indications

Tinea Pedis

ATC Classification

D01AC03
econazole
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
G01AF05
econazole
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS

Activity Summary

IC50 86 meas. best 7.54
Ki 45 meas. best 6.65
Kd 6 meas. best 7.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thromboxane-A synthase
CHEMBL1835
IC50 7.54 7.54 29.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 7.4 7.4 40.0 1
Trypanosoma cruzi
CHEMBL368
IC50 7.4 7.4 40.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 7.3 6.68 50.0 3
Lanosterol 14-alpha demethylase
CHEMBL3849
IC50 7.3 7.3 50.0 1
Mycocyclosin synthase
CHEMBL1681615
Kd 7.14 7.14 73.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 6.7 6.7 200.0 1
Sterol 14alpha-demethylase
CHEMBL5090
Kd 6.7 6.7 200.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.65 6.65 225.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.53 6.53 296.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 6.52 6.52 300.0 1
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase
CHEMBL4523494
IC50 6.51 6.51 310.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.5 6.5 320.0 1
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
Ki 6.49 6.49 325.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.42 6.42 379.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.4 6.4 400.0 1
Transient receptor potential cation channel subfamily M member 8
CHEMBL1075319
IC50 6.38 6.38 420.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.37 6.37 423.0 1
Delta-type opioid receptor
CHEMBL236
Ki 6.29 6.29 508.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.2 6.2 636.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.18 6.18 663.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.08 6.08 835.0 1
Unchecked
CHEMBL612545
Kd 6.06 5.6175 880.0 4
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
IC50 5.96 5.525 1100.0 2
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 5.94 5.94 1158.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.94 5.94 1152.0 1
Progesterone receptor
CHEMBL1909044
Ki 5.88 5.88 1332.0 1
Delta-type opioid receptor
CHEMBL236
IC50 5.84 5.84 1442.0 1
Histamine H2 receptor
CHEMBL1941
IC50 5.8 5.8 1592.0 1
Histamine H2 receptor
CHEMBL1941
Ki 5.8 5.8 1565.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.79 5.79 1622.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.79 5.79 1615.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 5.75 5.75 1789.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.74 5.74 1836.0 1
Substance-K receptor
CHEMBL2327
Ki 5.7 5.7 2011.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 5.67 5.67 2122.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.64 5.64 2311.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.62 5.62 2415.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.61 5.61 2435.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.58 5.58 2642.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.57 5.57 2677.0 1
Unchecked
CHEMBL612545
Ki 5.53 5.336 2930.0 5
Transient receptor potential cation channel subfamily M member 2
CHEMBL1250402
IC50 5.52 5.52 3000.0 1
Unchecked
CHEMBL612545
IC50 5.52 5.0286 3014.0 7
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.49 5.49 3256.0 1
D(4) dopamine receptor
CHEMBL219
Ki 5.49 5.49 3271.0 1
Adenosine receptor A3
CHEMBL256
IC50 5.49 5.49 3249.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.46 5.46 3446.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.39 5.39 4034.0 1
D(2) dopamine receptor
CHEMBL217
Ki 5.37 5.37 4269.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 1.0 nM Homo sapiens
Tmax 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thromboxane-A synthase IC50 = 29.0 nM 7.54 DRUGMATRIX: Thromboxane Synthetase enzyme inhibition (substrate: PGH2) -
Cytochrome P450 2C19 IC50 = 40.0 nM 7.4 DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Trypanosoma cruzi IC50 = 40.0 nM 7.4 DNDI: Chagas in Vitro, 96 hour -
Lanosterol 14-alpha demethylase IC50 = 50.0 nM 7.3 Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase as... 17194716
Cytochrome P450 3A4 IC50 = 50.0 nM 7.3 DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluorome... -
Mycocyclosin synthase Kd = 73.0 nM 7.14 Binding affinity to Mycobacterium tuberculosis H37Rv wild type CYP121 by titrati... 27002486
Cytochrome P450 2C9 IC50 = 200.0 nM 6.7 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Sterol 14alpha-demethylase Kd = 200.0 nM 6.7 Binding affinity to Mycobacterium tuberculosis CYP51 19075057
Sodium-dependent serotonin transporter Ki = 225.0 nM 6.65 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Muscarinic acetylcholine receptor M4 Ki = 296.0 nM 6.53 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Cytochrome P450 1A2 IC50 = 300.0 nM 6.52 DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase IC50 = 310.0 nM 6.51 Inhibition of CYP8B1 in human liver microsomes using D7-7alpha-hydroxy-4-cholest... -
Plasmodium falciparum IC50 = 320.0 nM 6.5 DNDI: Malaria in Vitro, 72 hour -
Steroid 17-alpha-hydroxylase/17,20 lyase Ki = 325.0 nM 6.49 In vitro inhibition of human Cytochrome P450 17A1 activity 12773039
Muscarinic acetylcholine receptor M3 Ki = 379.0 nM 6.42 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Cytochrome P450 2D6 IC50 = 400.0 nM 6.4 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Transient receptor potential cation channel subfamily M member 8 IC50 = 420.0 nM 6.38 Antagonist activity at TRPM8 (unknown origin) 27437828
Cytochrome P450 3A4 IC50 = 430.53 nM 6.37 Inhibition of CYP3A4 19128860
Cytochrome P450 3A4 IC50 = 430.0 nM 6.37 Inhibition of CYP3A4 (unknown origin) 31257085
Sodium-dependent serotonin transporter IC50 = 423.0 nM 6.37 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 610
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19075057 10.1128/aac.01237-08 Unchecked 6
18529046 10.1021/jm800009r Candida albicans 6
15267229 10.1021/jm049856v Candida albicans 6
18529046 10.1021/jm800009r Arthrodermataceae 6
14521410 10.1021/jm030191r Beta-lactamase 4
19564371 10.1128/aac.00550-09 Mycobacterium tuberculosis 4
25036789 10.1016/j.ejmech.2014.06.078 Indoleamine 2,3-dioxygenase 1 4
18694951 10.1128/aac.00517-08 Saccharomyces cerevisiae 4
- 10.6019/CHEMBL3392926 NON-PROTEIN TARGET 3
20014752 10.1021/tx900326k Hepatotoxicity 3
19380598 10.1128/aac.01384-08 Nakaseomyces glabratus 3
18529046 10.1021/jm800009r ADMET 2
15267229 10.1021/jm049856v Candida parapsilosis 2
20308390 10.1128/aac.01520-09 Mus musculus 2
- 10.1007/s00044-012-0129-4 Mycobacterium tuberculosis 2

Data from ChEMBL 36 via Core Engine