Compound: OSI-906
SMILES: O[C@]1(C[C@@H](c2nc(-c3cc4nc(-c5ccccc5)ccc4cc3)c6n2ccnc6N)C1)C
InChIKey: PKCDDUHJAFVJJB-VLZXCDOPSA-N
Synonyms: OSI-906, OSI 906, RefChem:928309, Linsitinib, 867160-71-2, OSI-906 (Linsitinib), Linsitinib(OSI-906), OSI906, OSI-906AA, ASP-7487, 3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol, C26H23N5O, MFCD12912153, 15A52GPT8T, CHEMBL1091644, MMV676605, Cis-3-(8-Amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutan-1-ol, cis-3-(8-amino-1-(2-phenyl-7-quinolinyl)imidazo(1,5-a)pyrazin-3-yl)-1-methylcyclobutanol, cis-3-[8-Amino-1-(2-phenyl-7-quinolinyl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutanol, (1s,3s)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutan-1-ol, Linsitinib [USAN], Kinome_3532, Linsitinib [USAN:INN], UNII-15A52GPT8T, cis-3-(8-Amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol, cis-3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutanol, (1s,3s)-3-[8-Amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol, CIS-3-(8-AMINO-1-(2-PHENYLQUINOLIN-7-YL)IMIDAZO(1,5-A)PYRAZIN-3-YL)-1-METHYLCYCLOBUTAN-1-OL, Linsitinib; OSI-906, LINSITINIB [INN], Linsitinib (USAN/INN), Linsitinib (OSI-906), Linsitinib(OSI-906)?, LINSITINIB [WHO-DD], MLS006010304, SCHEMBL400369, SCHEMBL400734, SCHEMBL400735, GTPL7423, orb1301148, CHEMBL1996234, SCHEMBL10255925, SCHEMBL29392484, CHEBI:91402, EX-A719, BDBM185150, DTXSID401007055, DTXSID901121553, GLXC-90207, HMS3295G15, HMS3654C19, BDBM50315887, NSC756652, NSC800784, s1091, AKOS024464740, CCG-264815, CS-0242, DB06075, EBC-221067, FO65116, NSC-756652, NSC-800784, PB22643, SDCCGSBI-0646932.P001, NCGC00250375-02, NCGC00250375-03, NCGC00250375-11, NCGC00250375-14, (1r,3r)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol., (1s,3r)-3-[8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol, AC-26953, AS-16999, HY-10191, SMR004700744, NS00073285, SW218150-2, D09925, SR-05000022538, Q6554803, SR-05000022538-1, BRD-K07667918-001-01-3, BRD-K86118762-001-01-8, BRD-K86118762-001-05-9, Q27163260, 3-[8-amino-1-(2-phenyl-7-quinolinyl)-3-imidazo[1,5-a]pyrazinyl]-1-methyl-1-cyclobutanol, 3-[8-amino-1-(2-phenyl-7-quinolyl)imidazo[1,5-a]pyrazin-3-yl]-1-methyl-cyclobutanol, (1r,3r)-3-[8-Amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutan-1-ol, (1s,3s)-3-(8-amino-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol, 1356958-77-4, 3-(8-amino-1-(2-phenylquinolin-7-yl)-2,3-dihydroimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol, 3-[8-AMINO-1-(2-PHENYL-QUINOLIN-7-YL)-IMIDAZO[1,5-A]PYRAZIN-3-YL]-1-METHYL-CYCLOBUTANOL, 867160-72-3, cis-3-[8-Amino-1-(2-phenyl-7-quinolinyl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutanol; OSI 906; OSI 906AA;, CYCLOBUTANOL, 3-(8-AMINO-1-(2-PHENYL-7-QUINOLINYL)IMIDAZO(1,5-A)PYRAZIN-3-YL)-1-METHYL-, CIS-, trans-3-[8-Amino-1-(2-phenyl-7-quinolinyl)imidazo[1,5-a]pyrazin-3-yl]-1-methylcyclobutanol
Theoretical properties:
molecular_formula: C26H23N5O
molecular_weight: 421.5 g/mol
exact_mass: 421.19026037 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 3
heavy_atom_count: 32
topological_polar_surface_area: 89.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Linsitinib is an imidazopyrazine that is imidazo[1,5-a]pyrazine substituted by 2-phenylquinolin-7-yl, cis-3-hydroxy-3-methylcyclobutyl, and amino groups at positions 1, 3, and 8, respectively. It is dual inhibitor of the IGF-1 receptor and insulin receptor (IC50 = 35 and 75 nM, respectively) that was previously in clinical development for the treatment of cancer and thyroid eye disease. It has a role as an antineoplastic agent, an antimycobacterial drug, an apoptosis inducer and an insulin-like growth factor receptor 1 antagonist. It is a member of cyclobutanes, a member of benzenes, a member of quinolines, a tertiary alcohol, an aromatic amine and an imidazopyrazine.
chebi: An imidazopyrazine that is imidazo[1,5-<em>a</em>]pyrazine substituted by 2-phenylquinolin-7-yl, <i>cis</i>-3-hydroxy-3-methylcyclobutyl, and amino groups at positions 1, 3, and 8, respectively. It is dual inhibitor of the IGF-1 receptor and insulin receptor (IC<small><sub>50</sub></small> = 35 and 75 nM, respectively) that was previously in clinical development for the treatment of cancer and thyroid eye disease.
chembl: LINSITINIB is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Linsitinib is an experimental drug candidate for the treatment of various types of cancer.  It is an inhibitor of the insulin receptor and of the insulin-like growth factor 1 receptor (IGF-1R).  This prevents tumor cell proliferation and induces tumor cell apoptosis.
Linsitinib was granted orphan drug designation for adrenocortical carcinoma in March 2012.
Phase II clinical trials were initiated for multiple myeloma, ovarian cancer, hepatocellular carcinoma, and NSCLC, but subsatisfactory results caused research for these indications to be discontinued. A phase III clinical trial found that linsitinib did not increase survival in patients with adrenocortical carcinoma. As of 2017, no clinical trials were in progress.