GSK2239633A   Click here for help

GtoPdb Ligand ID: 10416

Synonyms: compound 6 [PMID: 23409871] | GSK-2239633A
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: GSK2239633A is a arylsulfonamide class CC-chemokine receptor 4 (CCR4) antagonist. It binds the intracellular domain of the receptor, and therefore has an allosteric mode of action [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 159.17
Molecular weight 548.1
XLogP 2.9
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cccc2c1c(nn2Cc1cccc(c1)CNC(=O)C(O)(C)C)NS(=O)(=O)c1ccc(s1)Cl
Isomeric SMILES COc1cccc2c1c(nn2Cc1cccc(c1)CNC(=O)C(O)(C)C)NS(=O)(=O)c1ccc(s1)Cl
InChI InChI=1S/C24H25ClN4O5S2/c1-24(2,31)23(30)26-13-15-6-4-7-16(12-15)14-29-17-8-5-9-18(34-3)21(17)22(27-29)28-36(32,33)20-11-10-19(25)35-20/h4-12,31H,13-14H2,1-3H3,(H,26,30)(H,27,28)
InChI Key YTEVTHHGQMUPHC-UHFFFAOYSA-N
References
1. Cahn A, Hodgson S, Wilson R, Robertson J, Watson J, Beerahee M, Hughes SC, Young G, Graves R, Hall D et al.. (2013)
Safety, tolerability, pharmacokinetics and pharmacodynamics of GSK2239633, a CC-chemokine receptor 4 antagonist, in healthy male subjects: results from an open-label and from a randomised study.
BMC Pharmacol Toxicol, 14: 14. DOI: 10.1186/2050-6511-14-14 [PMID:23448278]
2. Procopiou PA, Barrett JW, Barton NP, Begg M, Clapham D, Copley RC, Ford AJ, Graves RH, Hall DA, Hancock AP et al.. (2013)
Synthesis and structure-activity relationships of indazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists.
J. Med. Chem., 56 (5): 1946-60. [PMID:23409871]