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).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fentanyl

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 Click here for help
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 Click here for help
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
International Nonproprietary Names Click here for help
INN number INN
1608 fentanyl
Synonyms Click here for help
Abstral® | Actiq® | Durogesic® | Effentora® | MCN-JR-4263-49 | R-4263 | Sublimaze®
Database Links Click here for help
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
Search Google for chemical match using the InChIKey PJMPHNIQZUBGLI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PJMPHNIQZUBGLI
Search PubMed clinical trials fentanyl
Search PubMed titles fentanyl
Search PubMed titles/abstracts fentanyl
Search UniChem for chemical match using the InChIKey PJMPHNIQZUBGLI-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone PJMPHNIQZUBGLI
Wikipedia Fentanyl