roflumilast   Click here for help

GtoPdb Ligand ID: 6962

Synonyms: ARQ-151/Zoryve® (roflumilast cream) | BY-217 | BYK-20869 | Daliresp® | Daxas®
Approved drug PDB Ligand Immunopharmacology Ligand
roflumilast is an approved drug (EMA (2010), FDA (2011))
Compound class: Synthetic organic
Comment: Roflumilast is a phosphodiesterase-4 inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 60.45
Molecular weight 402.03
XLogP 4
No. Lipinski's rules broken 0
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Canonical SMILES FC(Oc1ccc(cc1OCC1CC1)C(=O)Nc1c(Cl)cncc1Cl)F
Isomeric SMILES FC(Oc1ccc(cc1OCC1CC1)C(=O)Nc1c(Cl)cncc1Cl)F
InChI InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)
1. Huang Z, Mancini JA. (2006)
Phosphodiesterase 4 inhibitors for the treatment of asthma and COPD.
Curr Med Chem, 13 (27): 3253-62. [PMID:17168849]
2. Lebwohl MG, Papp KA, Stein Gold L, Gooderham MJ, Kircik LH, Draelos ZD, Kempers SE, Zirwas M, Smith K, Osborne DW et al.. (2020)
Trial of Roflumilast Cream for Chronic Plaque Psoriasis.
N Engl J Med, 383 (3): 229-239. [PMID:32668113]
3. Lunniss CJ, Cooper AW, Eldred CD, Kranz M, Lindvall M, Lucas FS, Neu M, Preston AG, Ranshaw LE, Redgrave AJ et al.. (2009)
Quinolines as a novel structural class of potent and selective PDE4 inhibitors: optimisation for oral administration.
Bioorg Med Chem Lett, 19 (5): 1380-5. [PMID:19195882]