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Compound Detail

CHEMBL104

CLOTRIMAZOLE
💊 Approved Drug
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💊 Approved Drug
Clc1ccccc1C(c1ccccc1)(c1ccccc1)n1ccnc1

Basic Information

ChEMBL ID CHEMBL104
Name CLOTRIMAZOLE
Phase Approved
Structure Type MOL
InChI Key VNFPBHJOKIVQEB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Abtrim Actavall BAY 5097 BAY-5097 Candiden Canesten Canesten af Canesten crm combi Canesten internal Canesten vc Clotrimazol Clotrimazole +18 more
106
Targets
244
Activities
4
Assay Types
2
PK Parameters
20
Publications
30
Known Names
18
Indications
1
Mechanisms

Molecular Properties

344.9
MW (Da)
5.38
ALogP
2
HBA
0
HBD
17.8
PSA (Ų)
0.45
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1975
Availability OTC
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Year 1970

Extended Properties

Molecular Formula C22H17ClN2
MW 344.85
Aromatic Rings 4
Heavy Atoms 25
NP-Likeness -0.58

Mechanism of Action

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

Indications

Candidiasis Infections Mycoses Pruritus Skin Diseases, Infectious Tinea Tinea Cruris Tinea Pedis Candidiasis, Oral Candidiasis, Vulvovaginal HIV Infections Otomycosis Vaginal Discharge Vaginitis Vaginosis, Bacterial Folliculitis Anemia, Sickle Cell Kidney Diseases

ATC Classification

A01AB18
clotrimazole
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: STOMATOLOGICAL PREPARATIONS
D01AC01
clotrimazole
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
G01AF02
clotrimazole
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS

Activity Summary

IC50 164 meas. best 8.74
Ki 51 meas. best 7.09
EC50 16 meas. best 6.88
Kd 13 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aromatase
CHEMBL1978
IC50 8.74 8.74 1.8 1
Trypanosoma cruzi
CHEMBL368
IC50 8.22 7.475 6.0 2
Thromboxane-A synthase
CHEMBL1835
IC50 7.85 7.85 14.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 7.8 7.335 16.0 2
Cytochrome P450 3A4
CHEMBL340
IC50 7.8 7.2983 16.0 6
Cytochrome P450 2C19
CHEMBL3622
IC50 7.8 6.465 16.0 2
Plasmodium falciparum
CHEMBL364
IC50 7.22 6.3642 60.0 24
Intermediate conductance calcium-activated potassium channel protein 4
CHEMBL4305
IC50 7.16 6.92 70.0 3
Unchecked
CHEMBL612545
Kd 7.16 6.0888 70.0 8
Mycocyclosin synthase
CHEMBL1681615
Kd 7.14 7.14 73.0 1
Nuclear receptor subfamily 1 group I member 3
CHEMBL5503
IC50 7.1 6.7533 80.0 3
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
Ki 7.09 7.09 81.5 1
Nuclear receptor subfamily 1 group I member 3
CHEMBL5503
Ki 7.0 7.0 100.0 1
14-alpha sterol demethylase
CHEMBL1681624
Kd 6.99 6.99 103.0 1
Lanosterol 14-alpha demethylase
CHEMBL3849
IC50 6.89 6.89 130.0 1
ATP-dependent molecular chaperone HSP82
CHEMBL1293251
EC50 6.88 6.34 133.0 2
Unchecked
CHEMBL612545
EC50 6.78 5.97 168.0 3
Sterol 14alpha-demethylase
CHEMBL5090
Kd 6.7 6.7 200.0 1
Plasmodium falciparum
CHEMBL364
EC50 6.55 6.51 280.2 2
Trichophyton rubrum
CHEMBL612649
IC50 6.52 6.52 300.0 1
Saccharomyces cerevisiae
CHEMBL361
IC50 6.4 6.4 400.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL1940
IC50 6.23 6.23 590.0 1
NIH3T3
CHEMBL614822
IC50 6.2 6.2 630.0 1
Mu-type opioid receptor
CHEMBL233
Ki 6.14 6.14 731.0 1
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase
CHEMBL4523494
IC50 6.1 6.1 800.0 1
Cytochrome P450 2C8
CHEMBL3721
IC50 6.09 6.09 803.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.05 6.05 899.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.05 6.05 883.0 1
Progesterone receptor
CHEMBL1909044
Ki 5.94 5.94 1144.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.9 5.9 1250.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 5.89 5.41 1300.0 3
Transitional endoplasmic reticulum ATPase
CHEMBL1075145
IC50 5.85 5.385 1400.0 2
Glucocorticoid receptor
CHEMBL2034
Ki 5.83 5.83 1481.0 1
C-C chemokine receptor type 4
CHEMBL2414
IC50 5.8 5.8 1600.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 5.79 5.79 1640.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.78 5.78 1654.0 1
Delta-type opioid receptor
CHEMBL236
Ki 5.76 5.76 1755.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.74 5.74 1802.0 1
C-X-C chemokine receptor type 1
CHEMBL4029
IC50 5.7 5.2617 1995.3 6
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.68 5.68 2104.0 1
Leishmania donovani
CHEMBL367
IC50 5.65 5.24 2230.0 2
Unchecked
CHEMBL612545
Ki 5.62 5.08 2410.0 6
Unchecked
CHEMBL612545
IC50 5.61 4.8142 2478.0 12
Vasopressin V2 receptor
CHEMBL1790
IC50 5.6 5.1975 2511.9 4
Kappa-type opioid receptor
CHEMBL237
Ki 5.6 5.6 2521.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.58 5.58 2647.0 1
Adenosine receptor A3
CHEMBL256
Ki 5.57 5.57 2686.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 5.57 5.57 2700.0 1
Leishmania chagasi
CHEMBL612790
IC50 5.55 5.55 2810.0 1
Transient receptor potential cation channel subfamily M member 2
CHEMBL1250402
IC50 5.52 5.52 3000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL - - Rattus norvegicus
Cmax 87.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aromatase IC50 = 1.8 nM 8.74 Inhibition of human placental microsome CYP19 20413308
Trypanosoma cruzi IC50 = 6.0 nM 8.22 DNDI: Chagas in Vitro, 96 hour -
Thromboxane-A synthase IC50 = 14.0 nM 7.85 DRUGMATRIX: Thromboxane Synthetase enzyme inhibition (substrate: PGH2) -
Cytochrome P450 3A4 IC50 = 16.0 nM 7.8 DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluorome... -
Cytochrome P450 2C9 IC50 = 16.0 nM 7.8 DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 2C19 IC50 = 16.0 nM 7.8 DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 3A4 IC50 = 20.0 nM 7.7 Inhibition of human cytochrome P450 3A4 12699389
Cytochrome P450 3A4 IC50 = 50.0 nM 7.3 Inhibition of CYP3A4 (unknown origin) 31257085
Cytochrome P450 3A4 IC50 = 50.0 nM 7.3 Inhibition of CYP3A4 19128860
Plasmodium falciparum IC50 = 60.0 nM 7.22 Antimalarial activity after 24 hrs against chloroquine-sensitive Plasmodium falc... 19113955
Plasmodium falciparum IC50 = 60.0 nM 7.22 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 b... 18278860
Plasmodium falciparum IC50 = 60.0 nM 7.22 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 17263523
Cytochrome P450 3A4 IC50 = 67.0 nM 7.17 Inhibition of recombinant human CYP3A4 using Luciferin-PPXE as substrate preincu... 31288127
Intermediate conductance calcium-activated potassium channel protein 4 IC50 = 70.0 nM 7.16 Inhibition of human cloned IK1 expressed in african green monkey COS7 cells by w... 19282171
Unchecked Kd = 70.0 nM 7.16 Binding affinity to Mycobacterium tuberculosis H37Rv CYP121A1 by UV-visible scan... 30837169
Intermediate conductance calcium-activated potassium channel protein 4 IC50 = 70.0 nM 7.16 Inhibition of IK1 19282171
Unchecked Kd = 70.0 nM 7.16 Binding affinity to Mycobacterium tuberculosis CYP121A1 expressed in Escherichia... 29185746
Mycocyclosin synthase Kd = 73.0 nM 7.14 Binding affinity to Mycobacterium tuberculosis H37Rv wild type CYP121 by titrati... 27002486
Nuclear receptor subfamily 1 group I member 3 IC50 = 80.0 nM 7.1 Inverse agonist activity at GST tagged-human CAR-LBD assessed as reduction in fl... 26717202
Steroid 17-alpha-hydroxylase/17,20 lyase Ki = 81.5 nM 7.09 In vitro inhibition of human Cytochrome P450 17A1 activity 12773039

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 1174
18973326 10.1021/jm800337r Nuclear receptor subfamily 1 group I member 3 39
22560629 10.1016/j.ejmech.2012.04.006 HEp-2 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20547793 10.1128/aac.00303-10 Candida albicans 13
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 12
38116435 10.1021/acsmedchemlett.3c00406 Mycobacterium tuberculosis 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23702472 10.1016/j.ejmech.2013.04.042 HEp-2 11
26881456 10.1021/acs.jmedchem.5b01264 Candida albicans 11
18983136 10.1021/jm800731b Nuclear receptor subfamily 1 group I member 3 10
12699389 10.1021/jm021012t ATP-dependent translocase ABCB1 10
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 8
- 10.6019/CHEMBL5303304 HEK-293T 8
18694951 10.1128/aac.00517-08 Saccharomyces cerevisiae 8
19075057 10.1128/aac.01237-08 Unchecked 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
20733039 10.1128/aac.00348-10 Candida albicans 7
23437772 10.1021/jm301749y Vasopressin V2 receptor 7

Data from ChEMBL 36 via Core Engine