| Width: | 250px |
| Tradename: | Recorlev |
| Dailymedid: | Levoketoconazole |
| Routes Of Administration: | By mouth |
| Atc Prefix: | H02 |
| Atc Suffix: | CA04 |
| Legal Us: | Rx-only |
| Legal Us Comment: | [1] |
| Cas Number: | 142128-57-2 |
| Pubchem: | 47576 |
| Drugbank: | DB05667 |
| Chemspiderid: | 43284 |
| Unii: | 2DJ8R0NT7K |
| Kegg: | D10950 |
| Chebi: | 47518 |
| Chembl: | 295698 |
| Pdb Ligand: | KLN |
| Synonyms: | COR-003; (2S,4R)-ketoconazole; NormoCort |
| Iupac Name: | 1-[4-(4-<nowiki/>{[(2''S'',4''R'')-2-(2,4-Dichlorophenyl)-2-(1''H''-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]ethanone |
| C: | 26 |
| H: | 28 |
| Cl: | 2 |
| N: | 4 |
| O: | 4 |
| Smiles: | CC(=O)N1CCN(CC1)c2ccc(cc2)OC[C@@H]3CO[C@@](O3)(Cn4ccnc4)c5ccc(cc5Cl)Cl |
| Stdinchi: | 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 |
| Stdinchikey: | XMAYWYJOQHXEEK-ZEQKJWHPSA-N |
Levoketoconazole, sold under the brand name Recorlev, is a steroidogenesis inhibitor that is used for the treatment of Cushing's syndrome.[2] [3] [4] [5] Levoketoconazole was approved for medical use in the United States in December 2021.[6] [7]
Levoketoconazole is the levorotatory or (2S,4R) enantiomer of ketoconazole, and it is an inhibitor of the enzymes CYP11B1 (11β-hydroxylase), CYP17A1 (17α-hydroxylase/17,20-lyase), and CYP21A2 (21-hydroxylase). It inhibits glucocorticoid biosynthesis and hence circulating levels of glucocorticoids, thereby treating Cushing's syndrome. In addition to its increased potency, the drug is 12-fold less potent than racemic ketoconazole in inhibiting CYP7A1 (cholesterol 7α-hydroxylase), theoretically resulting in further reduced interference with bile acid production and metabolite elimination and therefore less risk of hepatotoxicity. Levoketoconazole has also been found to inhibit CYP11A1 (cholesterol side-chain cleavage enzyme) and CYP51A1 (lanosterol-14α-demethylase), similarly but more potently relative to ketoconazole.[8]