levoketoconazole   Click here for help

GtoPdb Ligand ID: 11829

Synonyms: (2S,4R)-ketoconazole | COR-003 | COR003 | Recorlev®
Approved drug PDB Ligand
levoketoconazole is an approved drug (FDA (2021))
Compound class: Synthetic organic
Comment: Levoketoconazole is the pure (2S,4R) enantiomer of the approved drug ketoconazole. Like ketoconazole, levoketoconazole is orally available. It is a more potent inhibitor of glucocorticoid synthesis than the enantiomerically mixed ketoconazole formulation. Levoketoconazole reduces cortisol biosynthesis by inhibiting three key cytochrome P450 enzymes of the glucocorticoid synthesis pathway; 11β-hydroxylase (CYP11B1), 17α-hydroxylase/17,20-lyase (CYP17A1) and steroid 21-hydroxylase (CYP21A2).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 69.06
Molecular weight 530.15
XLogP 4.08
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc(c(c1)Cl)[C@@]1(OC[C@H](O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
Isomeric SMILES CC(=O)N1CCN(CC1)c1ccc(cc1)OC[C@@H]1CO[C@@](O1)(Cn1ccnc1)c1c(cc(cc1)Cl)Cl
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2021))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10206 levoketoconazole
Synonyms Click here for help
(2S,4R)-ketoconazole | COR-003 | COR003 | Recorlev®
Database Links Click here for help
CAS Registry No. 142128-57-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL295698
DrugBank Ligand DB05667
GtoPdb PubChem SID 461663385
PubChem CID 47576
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