nezulcitinib   Click here for help

GtoPdb Ligand ID: 11304

Synonyms: example 1 [WO2020051105A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The chemical structure for this Janus kinase inhibitor was obtained from the WHO's special release of proposed INNs for COVID-related therapeutics that was published in October 2020, with the proposed INN being nezulcitinib. The structure is a match to example 1 as claimed in Theravance's 2020 patent WO2020051105A1. Analysis of Theravance's pipeline webpage and ClinicalTrials.gov suggests that this is likely to be their clinical lead TD-0903, which they identify as a lung-selective JAK inhibitor, since TD-0903 had begun evaluation in COVID-19 patients. At the point of creating this entry (Nov 2020) there had been no formal name>structure disclosure. We will update this as further details become available.
In June 2021, Theravance announced that top-line results from patients with confirmed COVID-19 associated acute lung injury and impaired oxygenation, showed no statistically significant difference between nezulcitinib and placebo groups in terms of primary or secondary outcomes.
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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Rotatable bonds 7
Topological polar surface area 104.38
Molecular weight 527.3
XLogP 4.36
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCc1cc(O)ccc1c1ccc2c(c1)[nH]nc2c1nc2c([nH]1)C[C@H](N(C2)C(C)C)C(=O)N1CC(C1)N(C)C
Isomeric SMILES CCc1cc(O)ccc1c1ccc2c(c1)[nH]nc2c1nc2c([nH]1)C[C@H](N(C2)C(C)C)C(=O)N1CC(C1)N(C)C
InChI InChI=1S/C30H37N7O2/c1-6-18-11-21(38)8-10-22(18)19-7-9-23-24(12-19)33-34-28(23)29-31-25-13-27(37(17(2)3)16-26(25)32-29)30(39)36-14-20(15-36)35(4)5/h7-12,17,20,27,38H,6,13-16H2,1-5H3,(H,31,32)(H,33,34)/t27-/m0/s1
InChI Key VQIIUJSNIKEMCK-MHZLTWQESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[3-(dimethylamino)azetidin-1-yl]-[(6S)-2-[6-(2-ethyl-4-hydroxyphenyl)-1H-indazol-3-yl]-5-propan-2-yl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-6-yl]methanone
International Nonproprietary Names Click here for help
INN number INN
11732 nezulcitinib
Synonyms Click here for help
example 1 [WO2020051105A1]
Database Links Click here for help
CAS Registry No. 2412496-23-0 (source: WHO INN record)
GtoPdb PubChem SID 434321739
PubChem CID 146421275
Search Google for chemical match using the InChIKey VQIIUJSNIKEMCK-MHZLTWQESA-N
Search Google for chemicals with the same backbone VQIIUJSNIKEMCK
Search PubMed clinical trials nezulcitinib
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UniChem Compound Search for chemical match using the InChIKey VQIIUJSNIKEMCK-MHZLTWQESA-N
UniChem Connectivity Search for chemical match using the InChIKey VQIIUJSNIKEMCK-MHZLTWQESA-N