fentanyl   

GtoPdb Ligand ID: 1626

Synonyms: Abstral® | Actiq® | Durogesic® | Effentora® | MCN-JR-4263-49 | R-4263 | Sublimaze®
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
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
SMILES / InChI / InChIKey
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
InChI Key PJMPHNIQZUBGLI-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1968), EMA (2008))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
International Nonproprietary Names
INN number INN
1608 fentanyl
Synonyms
Abstral® | Actiq® | Durogesic® | Effentora® | MCN-JR-4263-49 | R-4263 | Sublimaze®
Database Links
BindingDB Ligand 50008984
CAS Registry No. 437-38-7 (source: DrugBank)
ChEBI CHEBI:119915
ChEMBL Ligand CHEMBL596
DrugBank Ligand DB00813
DrugCentral Ligand 1164
GtoPdb PubChem SID 135650258
PubChem CID 3345
RCSB PDB Ligand 7V7
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Wikipedia Fentanyl