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
Thumb
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
PropertyValueSource
Water Solubility0.356 mg/mLALOGPS
logP2.18ALOGPS
logP2.11ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area41.61 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.07 m3·mol-1ChemAxon
Polarizability22.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon