rolipram   Click here for help

GtoPdb Ligand ID: 5260

Synonyms: (±)-rolipram | (R,S)-rolipram
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rolipram is a a well-characterized PDE4 inhibitor that has been widely used in research to examine the role(s) played by PDE4 in autoimmune and inflammatory diseases [2-3], Alzheimer's disease [1] and cognition [4]. The INN-assigned preparation of rolipram is a racemic mixture of R-rolipram and S-rolipram. The structure shown here does not specify stereochemistry to represent the mixture. The two stereoisomers are represented on PubChem by CID 448055 and CID 158758, and by the entries on DrugBank linked to in the table above.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 47.56
Molecular weight 275.15
XLogP 1.89
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc(cc1OC1CCCC1)C1CNC(=O)C1
Isomeric SMILES COc1ccc(cc1OC1CCCC1)C1CNC(=O)C1
InChI InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 4A Hs Inhibitor Inhibition 9.0 pIC50 - 5
pIC50 9.0 (IC50 1x10-9 M) [5]
phosphodiesterase 4B Hs Inhibitor Inhibition 9.0 pIC50 - 5
pIC50 9.0 (IC50 1x10-9 M) [5]
phosphodiesterase 4D Hs Inhibitor Inhibition 7.2 pIC50 - 5
pIC50 7.2 (IC50 6.31x10-8 M) [5]
phosphodiesterase 4C Hs Inhibitor Inhibition 6.5 pIC50 - 5
pIC50 6.5 (IC50 3.16x10-7 M) [5]