Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL277535

BIFONAZOLE
🧪 Phase III
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase III
c1ccc(-c2ccc(C(c3ccccc3)n3ccnc3)cc2)cc1

Basic Information

ChEMBL ID CHEMBL277535
Name BIFONAZOLE
Phase Phase III
Structure Type MOL
InChI Key OCAPBUJLXMYKEJ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BAY H 4502 BAY-H-4502 Bifonazol Bifonazole D01AC10 Mycospor NSC-758954
15
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
7
Known Names
2
Indications
2
Mechanisms

Molecular Properties

310.4
MW (Da)
5.19
ALogP
2
HBA
0
HBD
17.8
PSA (Ų)
0.51
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Year 1981

Extended Properties

Molecular Formula C22H18N2
MW 310.40
Aromatic Rings 4
Heavy Atoms 24
NP-Likeness -0.67

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Lanosterol 14-alpha demethylase inhibitor INHIBITOR Lanosterol 14-alpha demethylase
HMG-CoA reductase inhibitor INHIBITOR 3-hydroxy-3-methylglutaryl-coenzyme A reductase

Indications

Onychomycosis Tinea Pedis

ATC Classification

D01AC10
bifonazole
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
D01AC60
bifonazole, combinations
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE

Activity Summary

IC50 19 meas. best 8.52
EC50 1 meas. best 4.75
Ki 1 meas. best 7.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
IC50 8.52 7.605 3.0 2
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
Ki 7.25 7.25 56.5 1
Lanosterol 14-alpha demethylase
CHEMBL3849
IC50 6.47 6.47 342.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 6.1 6.1 800.0 1
Steroid 17-alpha-hydroxylase/17,20 lyase
CHEMBL3522
IC50 6.1 6.1 790.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.5 5.5 3180.0 1
Leishmania donovani
CHEMBL367
IC50 5.26 5.26 5480.0 1
Cysteine protease ATG4B
CHEMBL1741221
IC50 5.07 5.07 8500.0 1
Leishmania chagasi
CHEMBL612790
IC50 5.05 5.05 8970.0 1
Phospholipase A2
CHEMBL4426
IC50 5.05 5.05 8890.0 1
Calpain-2 catalytic subunit
CHEMBL4143
IC50 4.83 4.83 14706.0 1
Unchecked
CHEMBL612545
IC50 4.77 4.63 17000.0 4
Unchecked
CHEMBL612545
EC50 4.75 4.75 17800.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
IC50 4.64 4.64 23000.0 1
Bile salt export pump
CHEMBL6020
IC50 4.57 4.57 27100.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 4.57 4.57 26800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.41 4.41 39300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 3.0 nM 8.52 DNDI: Chagas in Vitro, 96 hour -
Steroid 17-alpha-hydroxylase/17,20 lyase Ki = 56.5 nM 7.25 In vitro inhibition of human Cytochrome P450 17A1 activity 12773039
Trypanosoma cruzi IC50 = 204.0 nM 6.69 Antitrypanosomal activity against amastigote stage of Trypanosoma cruzi infected... 23927763
Lanosterol 14-alpha demethylase IC50 = 342.0 nM 6.47 Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase as... 17194716
Steroid 17-alpha-hydroxylase/17,20 lyase IC50 = 790.0 nM 6.1 Inhibition of human CYP17 expressed in Escherichia coli coexpressed with cytochr... 18674917
Cytochrome P450 3A4 IC50 = 800.0 nM 6.1 In vitro CYP3A4 Inhibition Assay: Cytochrome P450 is a large and diverse group o... -
Plasmodium falciparum IC50 = 3180.0 nM 5.5 DNDI: Malaria in Vitro, 72 hour -
Leishmania donovani IC50 = 5480.0 nM 5.26 DNDI: Leish (axenic) in Vitro, 72 hour -
Cysteine protease ATG4B IC50 = 8500.0 nM 5.07 PUBCHEM_BIOASSAY: Dose response confirmation of the uHTS fluorescent assay for i... -
Phospholipase A2 IC50 = 8890.0 nM 5.05 PUBCHEM_BIOASSAY: Dose response counterscreen of uHTS hits for ATG4B inhibitors ... -
Leishmania chagasi IC50 = 8970.0 nM 5.05 Antileishmanial activity against Leishmania infantum chagasi MHOM/BR/1972/LD pro... 28456033
Calpain-2 catalytic subunit IC50 = 14706.0 nM 4.83 PUBCHEM_BIOASSAY: Dose Response Confirmation for Calpain Inhibitors. (Class of a... -
Unchecked IC50 = 17000.0 nM 4.77 Inhibition of porcine heart malate dehydrogenase preincubated for 5 min followed... 34812616
Unchecked EC50 = 17800.0 nM 4.75 PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7K ce... -
Unchecked IC50 = 19720.0 nM 4.71 PUBCHEM_BIOASSAY: High Throughput Screening Assay used to Identify Novel Compoun... -
Indoleamine 2,3-dioxygenase 1 IC50 = 23000.0 nM 4.64 Inhibition of IDO1 (unknown origin) using L-tryptophan substrate incubated for 6... 25036789
Unchecked IC50 = 23200.0 nM 4.63 PUBCHEM_BIOASSAY: A High Throughput Confirmatory Assay used to Identify Novel Co... -
Trypanosoma brucei rhodesiense IC50 = 26800.0 nM 4.57 DNDI: HAT in Vitro, 72 hour -
Bile salt export pump IC50 = 27100.0 nM 4.57 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
NON-PROTEIN TARGET IC50 = 39300.0 nM 4.41 DNDI: Cytotoxicity in Vitro, 72 hour, in rat skeletal myoblast cells -

Literature References

PubMed DOI Target Context # Activities
17620378 10.1128/aac.00654-07 Colletotrichum graminicola 22
12061875 10.1021/jm011087h Candida albicans 11
12061875 10.1021/jm011087h Candida 10
7473549 10.1021/jm00021a011 Candida albicans 8
7473549 10.1021/jm00021a011 Candida 8
25036789 10.1016/j.ejmech.2014.06.078 Indoleamine 2,3-dioxygenase 1 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
16078834 10.1021/jm048997u Candida albicans 4
20014752 10.1021/tx900326k Hepatotoxicity 3
7473549 10.1021/jm00021a011 Oryctolagus cuniculus 3
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 3
19914077 10.1016/j.bmc.2009.10.041 Aspergillus flavus 2
18053730 10.1016/j.bmc.2007.10.082 Trichoderma viride 2
18053730 10.1016/j.bmc.2007.10.082 Talaromyces funiculosus 2
18053730 10.1016/j.bmc.2007.10.082 Aspergillus flavus 2
18053730 10.1016/j.bmc.2007.10.082 Aspergillus niger 2
19914077 10.1016/j.bmc.2009.10.041 Aspergillus niger 2
10956200 10.1021/jm0000822 No relevant target 2
19914077 10.1016/j.bmc.2009.10.041 Fulvia fulva 2
11714599 10.1016/s0960-894x(01)00609-6 Candida albicans 2

Data from ChEMBL 36 via Core Engine