Osilodrostat phosphateProduct ingredient for Osilodrostat
- Name
- Osilodrostat phosphate
- Drug Entry
- Osilodrostat
Osilodrostat is an inhibitor of 11β-hydroxylase (also referred to as CYP11B1), the enzyme that catalyzes the final step in the biosynthesis of endogenous cortisol.6 It is used to lower circulating cortisol levels in the treatment of Cushing's disease, a disorder in which cortisol levels are chronically and supraphysiologically elevated. Cushing's disease is often the result of ACTH hypersecretion secondary to a pituitary tumor, and surgical resection of the tumour is generally the treatment of choice.5 As an orally bioavailable drug therapy, osilodrostat provides a novel treatment option for patients in whom removal of the causative tumor is not an option or for whom previous pituitary surgery has not been curative.
Osilodrostat is manufactured by Novartis under the brand name Isturisa.6 It has undergone phase II clinical trials for the treatment of solid tumours, hypertension, and heart failure, but development for these indications was discontinued by Novartis in January 2013.4 Osilodrostat was approved for use in the EU in January 2020 for the treatment of endogenous Cushing's syndrome (i.e. Cushing's disease),4 and was granted FDA approval and Orphan Drug designation in the US in March 2020 for the same indication.9
- Accession Number
- DBSALT002092
- Structure
- Synonyms
- Osilodrostat phosphate
- External IDs
- LCI699-AZA
- UNII
- Y6581YAW9V
- CAS Number
- 1315449-72-9
- Weight
- Average: 325.236
Monoisotopic: 325.062771072 - Chemical Formula
- C13H13FN3O4P
- InChI Key
- FMCPYRDGUZBOJZ-BTQNPOSSSA-N
- InChI
- InChI=1S/C13H10FN3.H3O4P/c14-12-5-9(6-15)1-3-11(12)13-4-2-10-7-16-8-17(10)13;1-5(2,3)4/h1,3,5,7-8,13H,2,4H2;(H3,1,2,3,4)/t13-;/m1./s1
- IUPAC Name
- 3-fluoro-4-[(5R)-5H,6H,7H-pyrrolo[1,2-c]imidazol-5-yl]benzonitrile; phosphoric acid
- SMILES
- OP(O)(O)=O.FC1=C(C=CC(=C1)C#N)[C@H]1CCC2=CN=CN12
- External Links
- ChemSpider
- 35293688
- ChEMBL
- CHEMBL3707393
- Predicted Properties
Property Value Source Water Solubility 0.356 mg/mL ALOGPS logP 2.18 ALOGPS logP 2.11 Chemaxon logS -2.8 ALOGPS pKa (Strongest Basic) 7.15 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 41.61 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 62.07 m3·mol-1 Chemaxon Polarizability 22.56 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon