BIFONAZOLE

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Search structure


Synonyms	BAY H 4502 BAY-H-4502 Bifonazole D01AC10 Mycospor NSC-758954
Status
Molecule Category	UNKNOWN
ATC	D01AC10
UNII	QYJ305Z91O
EPA CompTox	DTXSID9045631


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	OCAPBUJLXMYKEJ-UHFFFAOYSA-N
Smiles	c1ccc(-c2ccc(C(c3ccccc3)n3ccnc3)cc2)cc1
InChI	InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H18N2
Molecular Weight	310.4
AlogP	5.19
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	4.0
Polar Surface Area	17.82
Molecular species	NEUTRAL
Aromatic Rings	4.0
Heavy Atoms	24.0

Assay Description	Organism	Bioactivity	Reference
In vitro inhibition of human Cytochrome P450 17A1 activity	Homo sapiens	56.5 nM
Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase assay	Homo sapiens	342.0 nM
Inhibition of human CYP17 expressed in Escherichia coli coexpressed with cytochrome P450 reductase	Homo sapiens	790.0 nM
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control	Mus musculus	55.0 %
Antitrypanosomal activity against amastigote stage of Trypanosoma cruzi infected in mouse NIH/3T3 cells after 48 hrs by Hoechst staining assay	Trypanosoma cruzi	204.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	121.06 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	115.65 %
Inhibition of IDO1 (unknown origin) at highest soluble concentration using L-tryptophan substrate incubated for 60 mins by HPLC	Homo sapiens	56.4 %
DNDI: Chagas in Vitro, 96 hour	Trypanosoma cruzi	3.0 nM
In vitro CYP3A4 Inhibition Assay: Cytochrome P450 is a large and diverse group of enzymes that catalyze the oxidation of organic substances. Some members of the CYP family contribute to the elimination of ATRA by catalyzing its 4-hydroxylation in the mammalian liver and skin, including that of humans as well as swine. Applicant evaluated the potential RAMBA activity of several azoles using pig liver microsomes, a rich source of CYP activity, comprising many different CYP 450 isoforms. Therefore, this approach, while a reasonable way to assess CYP inhibitors with broad activities may or may not be the best way to discover RAMBAs with selectivity for the skin, which has a much more narrow complement of CYP expression. As understanding in this area has progressed, a more specific CYP inhibition assay can be used to provide better predictivity of activity in human skin. Nevertheless, this assay may still be used as a general predictor of overall CYP activity.	Homo sapiens	800.0 nM
Inhibition of fungal keratinase activity at 10 mg/ml relative to control	Fungi	50.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	70.75 %
Inhibition of cytochrome P450 in Sprague-Dawley rat liver microsomes assessed as inhibition of NADPH-dependent retinoic acid oxidation at 10 uM incubated for 5 mins followed by retinoic acid addition and further incubated for 60 mins by HPLC analysis relative to control	Rattus norvegicus	89.0 %
Inhibition of cytochrome P450 in Sprague-Dawley rat liver microsomes assessed as inhibition of NADPH-dependent retinoic acid oxidation at 100 uM incubated for 5 mins followed by retinoic acid addition and further incubated for 60 mins by HPLC analysis relative to control	Rattus norvegicus	100.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-1.13 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.852 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %

Cross References

Resources	Reference
ChEBI	78692
ChEMBL	CHEMBL277535
DrugBank	DB04794
DrugCentral	370
FDA SRS	QYJ305Z91O
Human Metabolome Database	HMDB0015583
PharmGKB	PA164746464
PubChem	2378
SureChEMBL	SCHEMBL36803

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).