YSY

4-[(4R,5R)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl]-3-fluorobenzonitrile

Created: 2021-03-31
Last modified:  2021-06-16

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Chemical Details

Formal Charge0
Atom Count27
Chiral Atom Count1
Bond Count29
Aromatic Bond Count11
2D diagram of YSY
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Chemical Component Summary

Name4-[(4R,5R)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl]-3-fluorobenzonitrile
SynonymsOsilodrostat
Systematic Name (OpenEye OEToolkits)4-[(5~{R})-6,7-dihydro-5~{H}-pyrrolo[1,2-c]imidazol-5-yl]-3-fluoranyl-benzenecarbonitrile
FormulaC13 H10 F N3
Molecular Weight227.237
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01N#Cc1ccc(C2CCc3cncn32)c(F)c1
SMILESCACTVS3.385Fc1cc(ccc1[CH]2CCc3cncn23)C#N
SMILESOpenEye OEToolkits2.0.7c1cc(c(cc1C#N)F)C2CCc3n2cnc3
Canonical SMILESCACTVS3.385 Fc1cc(ccc1[C@H]2CCc3cncn23)C#N
Canonical SMILESOpenEye OEToolkits2.0.7 c1cc(c(cc1C#N)F)[C@H]2CCc3n2cnc3
InChIInChI1.03 InChI=1S/C13H10FN3/c14-12-5-9(6-15)1-3-11(12)13-4-2-10-7-16-8-17(10)13/h1,3,5,7-8,13H,2,4H2/t13-/m1/s1
InChIKeyInChI1.03 USUZGMWDZDXMDG-CYBMUJFWSA-N

Drug Info: DrugBank

DrugBank IDDB11837 
NameOsilodrostat
Groups
  • approved
  • investigational
DescriptionOsilodrostat is an inhibitor of 11β-hydroxylase (also referred to as CYP11B1), the enzyme that catalyzes the final step in the biosynthesis of endogenous cortisol.[L12123] 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.[A191910] 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.[L12123] 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.[A191850] Osilodrostat was approved for use in the EU in January 2020 for the treatment of endogenous Cushing's syndrome (i.e. Cushing's disease),[A191850] and was granted FDA approval and Orphan Drug designation in the US in March 2020 for the same indication.[L12162]
Synonyms
  • Osilodrostat
  • Osilodrostat phosphate
Brand NamesIsturisa
IndicationOsilodrostat is indicated for the treatment of adult patients with Cushing's disease for whom pituitary surgery is not an option or has not been curative.[L12123,A191850]
Categories
  • Antiadrenal Preparations
  • Anticorticosteroids
  • Cortisol Synthesis Inhibitors
  • Cytochrome P-450 CYP11B2, antagonists & inhibitors
  • Cytochrome P-450 CYP1A2 Inhibitors
ATC-CodeH02CA02
CAS number928134-65-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 11B1, mitochondrialMALRAKAEVCMAVPWLSLQRAQALGTRAARVPRTVLPFEAMPRRPGNRWL...unknowninhibitor
Cytochrome P450 11B2, mitochondrialMALRAKAEVCVAAPWLSLQRARALGTRAARAPRTVLPFEAMPQHPGNRWL...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknownsubstrate
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknownsubstrate,inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL3099695
PubChem 44139752
ChEMBL CHEMBL3099695