celecoxib   Click here for help

GtoPdb Ligand ID: 2892

Synonyms: Celecox® | Elyxyb® (DFN-15; oral solution) | Onsenal® | SC-58635 [4] | SC58635
Approved drug PDB Ligand Immunopharmacology Ligand
celecoxib is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Celecoxib is a non-steroidal anti-inflammatory drug (NSAID) [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 85.84
Molecular weight 381.08
XLogP 3.89
No. Lipinski's rules broken 0
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Canonical SMILES Cc1ccc(cc1)c1cc(nn1c1ccc(cc1)S(=O)(=O)N)C(F)(F)F
Isomeric SMILES Cc1ccc(cc1)c1cc(nn1c1ccc(cc1)S(=O)(=O)N)C(F)(F)F
InChI InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
carbonic anhydrase 12 Hs Inhibitor Inhibition 7.7 pKi - 5
pKi 7.7 (Ki 1.8x10-8 M) [5]
COX-2 Primary target of this compound Hs Inhibitor Inhibition 6.5 – 8.7 pIC50 - 1-2
pIC50 8.7 (IC50 2x10-9 M) [1]
pIC50 6.5 (IC50 3x10-7 M) [2]
COX-1 Hs Inhibitor Inhibition 4.0 – 4.8 pIC50 - 2,4
pIC50 4.0 – 4.8 (IC50 1x10-4 – 1.5x10-5 M) [2,4]