pasireotide   Click here for help

GtoPdb Ligand ID: 2018

Synonyms: pasireotide diaspartate | Signifor® | SOM 230 | SOM 320 | SOM-230
Approved drug
pasireotide is an approved drug (FDA and EMA (2012))
Comment: Cyclic peptide analog of somatostatin. This compound is represented on ChEMBL with slightly different stereochemistry by CHEMBL3039583.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Click here for help
Canonical SMILES NCCCCC1NC(=O)C(NC(=O)C(NC(=O)C2N(C(=O)C(NC(=O)C(NC1=O)Cc1ccc(cc1)OCc1ccccc1)Cc1ccccc1)CC(C2)OC(=O)NCCN)c1ccccc1)Cc1c[nH]c2c1cccc2
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)OCc1ccccc1)Cc1ccccc1)C[C@@H](C2)OC(=O)NCCN)c1ccccc1)Cc1c[nH]c2c1cccc2
InChI InChI=1S/C58H66N10O9/c59-27-13-12-22-46-52(69)64-47(30-38-23-25-42(26-24-38)76-36-39-16-6-2-7-17-39)53(70)66-49(31-37-14-4-1-5-15-37)57(74)68-35-43(77-58(75)61-29-28-60)33-50(68)55(72)67-51(40-18-8-3-9-19-40)56(73)65-48(54(71)63-46)32-41-34-62-45-21-11-10-20-44(41)45/h1-11,14-21,23-26,34,43,46-51,62H,12-13,22,27-33,35-36,59-60H2,(H,61,75)(H,63,71)(H,64,69)(H,65,73)(H,66,70)(H,67,72)/t43-,46+,47+,48-,49+,50+,51+/m1/s1
1. Cescato R, Loesch KA, Waser B, M├Ącke HR, Rivier JE, Reubi JC, Schonbrunn A. (2010)
Agonist-biased signaling at the sst2A receptor: the multi-somatostatin analogs KE108 and SOM230 activate and antagonize distinct signaling pathways.
Mol Endocrinol, 24 (1): 240-9. [PMID:19910453]
2. Kao YJ, Ghosh M, Schonbrunn A. (2011)
Ligand-dependent mechanisms of sst2A receptor trafficking: role of site-specific phosphorylation and receptor activation in the actions of biased somatostatin agonists.
Mol Endocrinol, 25 (6): 1040-54. [PMID:21493671]
3. Schmid HA, Schoeffter P. (2004)
Functional activity of the multiligand analog SOM230 at human recombinant somatostatin receptor subtypes supports its usefulness in neuroendocrine tumors.
Neuroendocrinology, 80 Suppl 1: 47-50. [PMID:15477717]