lepzacitinib   Click here for help

GtoPdb Ligand ID: 12871

Synonyms: example 117 [WO2019090158A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The structure for lepzacitinib was obtained from proposed INN list 129 (August 2023) where it is described as a Janus kinase inhibitor and anti-inflammatory agent. It is one of the compounds claimed in patent WO2019090158A1 [1]. Aclaris have three JAK inhibitors in their development pipeline, two of which are in clinical assessment: ATI-1777 (a soft inhibitor for topical applications such as atopic dermatitis), and ATI-2138 (a dual ITK/JAK3) inhibitor for T cell-mediated autoimmune diseases. Lepzacitinib is most likely ATI-1777.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 106.82
Molecular weight 355.39
XLogP 0.53
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOC(=O)C1=C(C2=C(NC=C2)N=C1)N[C@@H]3CCCN(C3)C(=O)CC#N
Isomeric SMILES C(#N)CC(=O)N1C[C@@H](CCC1)NC2=C3C(=NC=C2C(=O)OCC)NC=C3
InChI InChI=1S/C18H21N5O3/c1-2-26-18(25)14-10-21-17-13(6-8-20-17)16(14)22-12-4-3-9-23(11-12)15(24)5-7-19/h6,8,10,12H,2-5,9,11H2,1H3,(H2,20,21,22)/t12-/m1/s1
InChI Key QQOPOYMFJLUSBI-GFCCVEGCSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
ethyl 4-[[(3R)-1-(2-cyanoacetyl)piperidin-3-yl]amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxylate
Synonyms Click here for help
example 117 [WO2019090158A1]
Database Links Click here for help
BindingDB Ligand 493018
CAS Registry No. 2321488-47-3 (source: WHO INN record)
GtoPdb PubChem SID 485205992
PubChem CID 138624627
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UniChem Connectivity Search for chemical match using the InChIKey QQOPOYMFJLUSBI-GFCCVEGCSA-N