Linsitinib

Linsitinib
Names
	IUPAC name 3-[8-Amino-1-(2-phenyl-7-quinolyl)imidazo[1,5-a]pyrazin-3-yl]-1-methyl-cyclobutanol
	Other names OSI-906
Identifiers
CAS Number	867160-71-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1091644;
ChemSpider	21391708;
KEGG	D09925;
	InChI InChI=1S/C26H23N5O/c1-26(32)14-19(15-26)25-30-22(23-24(27)28-11-12-31(23)25)18-8-7-17-9-10-20(29-21(17)13-18)16-5-3-2-4-6-16/h2-13,19,32H,14-15H2,1H3,(H2,27,28) Key: PKCDDUHJAFVJJB-UHFFFAOYSA-N; InChI=1/C26H23N5O/c1-26(32)14-19(15-26)25-30-22(23-24(27)28-11-12-31(23)25)18-8-7-17-9-10-20(29-21(17)13-18)16-5-3-2-4-6-16/h2-13,19,32H,14-15H2,1H3,(H2,27,28)/t19-,26+ Key: PKCDDUHJAFVJJB-VLZXCDOPBI;
	SMILES C[C@]1(C[C@@H](C1)C2=NC(=C3N2C=CN=C3N)C4=CC5=C(C=CC(=N5)C6=CC=CC=C6)C=C4)O;
Properties
Chemical formula	C26H23N5O
Molar mass	421.50 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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).^[1] This prevents tumor cell proliferation and induces tumor cell apoptosis.^[2]

Linsitinib was granted orphan drug designation for adrenocortical carcinoma in March 2012.^[3]

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.^[3] A phase III clinical trial found that linsitinib did not increase survival in patients with adrenocortical carcinoma.^[4] As of 2017, no clinical trials were in progress.^[3]

References

↑ Mulvihill, MJ; Cooke, A; Rosenfeld-Franklin, M; Buck, E; Foreman, K; Landfair, D; O'Connor, M; Pirritt, C; et al. (2009). "Discovery of OSI-906: A selective and orally efficacious dual inhibitor of the IGF-1 receptor and insulin receptor". Future medicinal chemistry. 1 (6): 1153–71. doi:10.4155/fmc.09.89. PMID 21425998.
↑ "Linsitinib". NCI Drug Dictionary. National Cancer Institute. Retrieved October 16, 2012.
1 2 3 "Linsitinib - AdisInsight". adisinsight.springer.com.
↑ Fassnacht M, Berruti A, Baudin E, Demeure MJ, Gilbert J, Haak H, Kroiss M, Quinn DI, Hesseltine E, Ronchi CL, Terzolo M, Choueiri TK, Poondru S, Fleege T, Rorig R, Chen J, Stephens AW, Worden F, Hammer GD (1 April 2015). "Linsitinib (OSI-906) versus placebo for patients with locally advanced or metastatic adrenocortical carcinoma: a double-blind, randomised, phase 3 study". The Lancet Oncology. 16 (4): 426–35. doi:10.1016/S1470-2045(15)70081-1. PMID 25795408.

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[1] Mulvihill, MJ; Cooke, A; Rosenfeld-Franklin, M; Buck, E; Foreman, K; Landfair, D; O'Connor, M; Pirritt, C; et al. (2009). "Discovery of OSI-906: A selective and orally efficacious dual inhibitor of the IGF-1 receptor and insulin receptor". Future medicinal chemistry. 1 (6): 1153–71. doi:10.4155/fmc.09.89. PMID 21425998.

[2] "Linsitinib". NCI Drug Dictionary. National Cancer Institute. Retrieved October 16, 2012.

[springer.com-3] 1 2 3 "Linsitinib - AdisInsight". adisinsight.springer.com.

[4] Fassnacht M, Berruti A, Baudin E, Demeure MJ, Gilbert J, Haak H, Kroiss M, Quinn DI, Hesseltine E, Ronchi CL, Terzolo M, Choueiri TK, Poondru S, Fleege T, Rorig R, Chen J, Stephens AW, Worden F, Hammer GD (1 April 2015). "Linsitinib (OSI-906) versus placebo for patients with locally advanced or metastatic adrenocortical carcinoma: a double-blind, randomised, phase 3 study". The Lancet Oncology. 16 (4): 426–35. doi:10.1016/S1470-2045(15)70081-1. PMID 25795408.