lorpucitinib   Click here for help

GtoPdb Ligand ID: 10631

Synonyms: compound 2 [PMID: 32134643] | example 1 [WO2018112379A1]
Compound class: Synthetic organic
Comment: The chemical structure that was submitted to the WHO for the INN lorpucitinib is identical to the structure of example 1 that is claimed as a pan-Janus kinase inhibitor in Janssen's patent WO2018112379A1 [1]. Based on structural conformation this is an exact match to PubChem SID 395564298, and this is associated to CID 134611548. However, this CID does not specify the stereochemical conformation as described in the patent or as stipulated in the INN submission. The chemical structure was disclosed in March 2020 as a JAK inhibitor that is intended for the treatment of inflammatory bowel disease [2]. Its activity is restricted to the gut by virtue of its permeability and physicochemical properties, and this limits systemic exposure and the potential for on-target adverse events.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 119.62
Molecular weight 408.23
XLogP 1.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#CCC1CCC(CC1)n1c(CC(=O)NCC(O)(C)C)nc2c1c1cc[nH]c1nc2
Isomeric SMILES N#CC[C@@H]1CC[C@H](CC1)n1c(CC(=O)NCC(O)(C)C)nc2c1c1cc[nH]c1nc2
InChI InChI=1S/C22H28N6O2/c1-22(2,30)13-26-19(29)11-18-27-17-12-25-21-16(8-10-24-21)20(17)28(18)15-5-3-14(4-6-15)7-9-23/h8,10,12,14-15,30H,3-7,11,13H2,1-2H3,(H,24,25)(H,26,29)/t14-,15-
InChI Key NJKMSBSVJSQUBU-SHTZXODSSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-{1-[trans-4-(cyanomethyl)cyclohexyl]-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2-yl}-N-(2-hydroxy-2-methylpropyl)acetamide
International Nonproprietary Names Click here for help
INN number INN
11296 lorpucitinib
Synonyms Click here for help
compound 2 [PMID: 32134643] | example 1 [WO2018112379A1]
Database Links Click here for help
GtoPdb PubChem SID 404859078
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