Levoketoconazole

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Column 1
Recorlev
COR-003; (2S,4R)-ketoconazole; NormoCort
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}
US DailyMed: Levoketoconazole
By mouth
H02CA04 (WHO)
US: ℞-only
IUPAC name
1-[4-(4-{[(2S,4R)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]ethanone
142128-57-2
47576
DB05667
43284
2DJ8R0NT7K
D10950
CHEBI:47518
ChEMBL295698
KLN (PDBe, RCSB PDB)
DTXSID60161949
C26H28Cl2N4O4
531.43 g·mol−1
Interactive image
SMILES
CC(=O)N1CCN(CC1)c2ccc(cc2)OC[C@@H]3COC@@(Cn4ccnc4)c5ccc(cc5Cl)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/s1Key:XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Levoketoconazole, sold under the brand name Recorlev, is a steroidogenesis inhibitor that is used for the treatment of Cushing's syndrome. Levoketoconazole was approved for medical use in the United States in December 2021.

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.

In a systematic review of levoketoconazole, published in 2024, it was found to be effective in the management of Cushing Syndrome.

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• Clinical trial number NCT03277690 for "A Study to Assess the Safety and Efficacy of Levoketoconazole in the Treatment of Endogenous Cushing's Syndrome" at ClinicalTrials.gov
• Clinical trial number NCT01838551 for "Treatment for Endogenous Cushing's Syndrome (SONICS)" at ClinicalTrials.gov

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