delgocitinib   Click here for help

GtoPdb Ligand ID: 9619

Synonyms: Corectim® | ent-60 [4] | JTE-052 | JTE052
Approved drug PDB Ligand Immunopharmacology Ligand
delgocitinib is an approved drug (Japan (2020))
Compound class: Synthetic organic
Comment: Delgocitinib (JTE-052) is an ATP-competitive pna-Janus kinase (JAK) inhibitor in development for anti-inflammatory potential [5]. The chemical structure is disclosed in [4]. The pharmacology of JTE-052 was previously reported in [5]. Based on the developer's pipeline and patent claims, and on the structure submitted to the WHO for the INN delgocitinib, JTE-052 is likely to be compound 6 as claimed in patent US20140187534 [3]. Compound 6 is the most potent (lowest IC50) optically active stereoisomer with the correct structure in the patent, although stereochemistry has not rendered unambiguously in the patent extraction, and an IUPAC name is not provided.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 88.91
Molecular weight 310.15
XLogP 1.25
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES N#CCC(=O)N1CC(C21CCN(C2)c1ncnc2c1cc[nH]2)C
Isomeric SMILES N#CCC(=O)N1C[C@@H]([C@]21CCN(C2)c1ncnc2c1cc[nH]2)C
InChI InChI=1S/C16H18N6O/c1-11-8-22(13(23)2-5-17)16(11)4-7-21(9-16)15-12-3-6-18-14(12)19-10-20-15/h3,6,10-11H,2,4,7-9H2,1H3,(H,18,19,20)/t11-,16-/m0/s1
InChI Key LOWWYYZBZNSPDT-ZBEGNZNMSA-N
References
1. Dhillon S. (2020)
Delgocitinib: First Approval.
Drugs, 80 (6): 609-615. [PMID:32166597]
2. Nakagawa H, Nemoto O, Igarashi A, Saeki H, Kaino H, Nagata T. (2020)
Delgocitinib ointment, a topical Janus kinase inhibitor, in adult patients with moderate to severe atopic dermatitis: A phase 3, randomized, double-blind, vehicle-controlled study and an open-label, long-term extension study.
J Am Acad Dermatol, 82 (4): 823-831. [PMID:32029304]
3. Niji S, Shiozaki M, Miura T, Hara Y, Yamanaka H, Maeda K, Hori A, Inoue M, Hase Y. (2014)
Nitrogen-containing spirocyclic compounds and pharmaceutical uses thereof.
Patent number: US20140187534. Assignee: Japan Tobacco Inc.. Priority date: 31/07/2009. Publication date: 03/07/2014.
4. Noji S, Hara Y, Miura T, Yamanaka H, Maeda K, Hori A, Yamamoto H, Obika S, Inoue M, Hase Y et al.. (2020)
Discovery of a Janus Kinase Inhibitor Bearing a Highly Three-Dimensional Spiro Scaffold: JTE-052 (Delgocitinib) as a New Dermatological Agent to Treat Inflammatory Skin Disorders.
J Med Chem, 63 (13): 7163-7185. [PMID:32511913]
5. Tanimoto A, Ogawa Y, Oki C, Kimoto Y, Nozawa K, Amano W, Noji S, Shiozaki M, Matsuo A, Shinozaki Y et al.. (2015)
Pharmacological properties of JTE-052: a novel potent JAK inhibitor that suppresses various inflammatory responses in vitro and in vivo.
Inflamm Res, 64 (1): 41-51. [PMID:25387665]
6. Worm M, Bauer A, Elsner P, Mahler V, Molin S, Nielsen TSS. (2020)
Efficacy and safety of topical delgocitinib in patients with chronic hand eczema: data from a randomized, double-blind, vehicle-controlled phase IIa study.
Br J Dermatol, 182 (5): 1103-1110. [PMID:31466119]