LEVOKETOCONAZOLE


Synonyms	(-)-(2s,4r)-ketoconazole 2s,4r ketoconazole 2s,4r-ketoconazole COR-003 COR003 DIO-902 Extina Ketoconazole, (2s,4r)- Ketosidin Ketozole Levoketoconazole Nizoral Nizoral A-D Normocort Panfungol R-41400 Xolegel
Status
Molecule Category	UNKNOWN
UNII	R9400W927I
EPA CompTox	DTXSID60161949


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

Structure


InChI Key	XMAYWYJOQHXEEK-ZEQKJWHPSA-N
Smiles	CC(=O)N1CCN(c2ccc(OC[C@@H]3CO[C@@](Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1
InChI	InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H28Cl2N4O4
Molecular Weight	531.44
AlogP	4.21
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	7.0
Polar Surface Area	69.06
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	36.0

Assay Description	Organism	Bioactivity
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.77 %
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	-0.24 %	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	-0.24 %
Inhibition of CYP3A4M in human liver microsomes using midazolam as substrate in presence of NADPH incubated for 10 mins by LC-MS/MS analysis	Homo sapiens	26.9 nM

Related Entries

Cross References

Resources	Reference
ChEBI	47518
ChEMBL	CHEMBL295698
DrugBank	DB05667
FDA SRS	R9400W927I
Human Metabolome Database	HMDB0012242
PDB	KLN
PharmGKB	PA450146
PubChem	47576
SureChEMBL	SCHEMBL41473
ZINC	ZINC000000643153

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).

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).