prednisolone   Click here for help

GtoPdb Ligand ID: 2866

Synonyms: DELTA.1-Cortisol | Orapred® | Pediapred®
Approved drug PDB Ligand Immunopharmacology Ligand
prednisolone is an approved drug (FDA (1955))
Compound class: Synthetic organic
Comment: Prednisolone is a synthetic glucocorticoid. Marketed formulations may contain prednisolone sodium phosphate, prednisolone acetate, prednisolone hexanoate or prednisolone.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 94.83
Molecular weight 360.19
XLogP 1.02
No. Lipinski's rules broken 0
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Isomeric SMILES OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
InChI InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
1. Coghlan MJ, Kym PR, Elmore SW, Wang AX, Luly JR, Wilcox D, Stashko M, Lin CW, Miner J, Tyree C et al.. (2001)
Synthesis and characterization of non-steroidal ligands for the glucocorticoid receptor: selective quinoline derivatives with prednisolone-equivalent functional activity.
J Med Chem, 44 (18): 2879-85. [PMID:11520196]
2. Lind U, Greenidge P, Gillner M, Koehler KF, Wright A, Carlstedt-Duke J. (2000)
Functional probing of the human glucocorticoid receptor steroid-interacting surface by site-directed mutagenesis. Gln-642 plays an important role in steroid recognition and binding.
J Biol Chem, 275 (25): 19041-9. [PMID:10747884]
3. Ripa L, Edman K, Dearman M, Edenro G, Hendrickx R, Ullah V, Chang HF, Lepistö M, Chapman D, Geschwindner S et al.. (2018)
Discovery of a Novel Oral Glucocorticoid Receptor Modulator (AZD9567) with Improved Side Effect Profile.
J Med Chem, 61 (5): 1785-1799. [PMID:29424542]