Levoketoconazole is the 2S,4R enantiomer of ketoconazole and is an orally active steroidogenesis inhibitor. It inhibits key cytochrome P450 enzymes involved in the biosynthesis of cortisol and is used for the treatment of endogenous Cushing's syndrome.
Levoketoconazole primarily inhibits enzymes involved in steroid hormone synthesis, including CYP11B1 (11β-hydroxylase), CYP11A1 and CYP17A1. This inhibition reduces cortisol production and can help control excessive cortisol levels associated with Cushing's syndrome.
Levoketoconazole is a specialized steroidogenesis inhibitor API requiring controlled synthesis, stereochemical control, purification and comprehensive analytical testing.
The quality of Levoketoconazole API is evaluated using parameters such as identity, assay, related substances, stereochemical purity, water content, residual solvents and elemental impurities.
CAS Number: 142128-57-2
Molecular Formula: C26H28Cl2N4O4
Molecular Weight: 531.43 g/mol
Chemical Name: (2S,4R)-Ketoconazole
Molecule Type: Synthetic Small Molecule
Drug Class: Steroidogenesis Inhibitor
Therapeutic Class: Cortisol Synthesis Inhibitor
Therapeutic Area: Endocrinology
ATC Code: H02CA04
Levoketoconazole reduces cortisol synthesis by inhibiting several cytochrome P450 enzymes involved in adrenal steroidogenesis.
The principal enzymatic targets include:
Inhibition of these enzymes decreases steroid hormone biosynthesis, particularly cortisol production.
Levoketoconazole is used for the treatment of endogenous Cushing's syndrome, particularly to reduce excessive cortisol production. It is supplied as an oral pharmaceutical product.
Potential pharmaceutical and research applications include:
Levoketoconazole is the pure 2S,4R enantiomer of ketoconazole. Stereochemical purity is therefore a critical quality attribute for the API.
Levoketoconazole is described as a white or almost white crystalline powder. It is very slightly soluble in water and soluble in aqueous solutions below pH 2.
A controlled API manufacturing process may include:
Typical Levoketoconazole API testing may include:
Store Levoketoconazole API in a tightly closed container under controlled pharmaceutical storage conditions, protected from excessive moisture, heat and direct light. Final storage conditions should be based on validated stability data and the approved product/API specification.
Levoketoconazole is relevant to research and pharmaceutical development involving:
| Parameter | Specification |
|---|---|
| Appearance | White to off-white crystalline powder |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | 98.0% – 102.0% |
| Loss on Drying | NMT 1.0% |
| Residue on Ignition | NMT 0.5% |
| Heavy Metals | NMT 10 ppm |
| Individual Impurity | ≤ 0.5% |
| Total Impurities | ≤ 1.5% |
| Water Content | NMT 1.0% |