fentanyl   Click here for help

GtoPdb Ligand ID: 1626

Synonyms: Abstral® | Actiq® | Durogesic® | Effentora® | MCN-JR-4263-49 | R-4263 | Sublimaze®
Approved drug PDB Ligand
fentanyl is an approved drug (FDA (1968), EMA (2008))
Compound class: Synthetic organic
Comment: Fentanyl is a potent, synthetic, addiction-forming narcotic analgesic. Marketed formulations contain the citrate salt (PubChem CID 13810).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 23.55
Molecular weight 336.22
XLogP 3.94
No. Lipinski's rules broken 0
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Canonical SMILES CCC(=O)N(c1ccccc1)C1CCN(CC1)CCc1ccccc1
Isomeric SMILES CCC(=O)N(c1ccccc1)C1CCN(CC1)CCc1ccccc1
InChI InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
μ receptor Rn Agonist Full agonist 9.4 pKi - 1
pKi 9.4 [1]
μ receptor Primary target of this compound Hs Agonist Full agonist 9.2 pKi - 2
pKi 9.2 [2]
κ receptor Hs Agonist Partial agonist 7.1 pKi - 2
pKi 7.1 [2]
δ receptor Hs Agonist Full agonist 6.8 pKi - 2
pKi 6.8 [2]