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CHEBI:119915 - fentanyl

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name fentanyl
ChEBI ID CHEBI:119915
Definition The carboxamide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:310077, CHEBI:5012
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Formula C22H28N2O
Net Charge 0
Average Mass 336.47050
Monoisotopic Mass 336.220
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
InChIKey PJMPHNIQZUBGLI-UHFFFAOYSA-N
SMILES CCC(=O)N(C1CCN(CC1)CCc1ccccc1)c1ccccc1
Roles Classification
Biological Role(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
Application(s): intravenous anaesthetic

anaesthetic
Substance which produces loss of feeling or sensation.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
anaesthesia adjuvant
Any substance that possesses little anaesthetic effect by itself, but which enhances or potentiates the anaesthetic action of other drugs when given at the same time.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fentanyl (CHEBI:119915) has role μ-opioid receptor agonist (CHEBI:55322)
fentanyl (CHEBI:119915) has role adjuvant (CHEBI:60809)
fentanyl (CHEBI:119915) has role anaesthesia adjuvant (CHEBI:60807)
fentanyl (CHEBI:119915) has role anaesthetic (CHEBI:38867)
fentanyl (CHEBI:119915) has role intravenous anaesthetic (CHEBI:38877)
fentanyl (CHEBI:119915) has role opioid analgesic (CHEBI:35482)
fentanyl (CHEBI:119915) is a anilide (CHEBI:13248)
fentanyl (CHEBI:119915) is a monocarboxylic acid amide (CHEBI:29347)
fentanyl (CHEBI:119915) is a piperidines (CHEBI:26151)
Incoming fentanyl citrate (CHEBI:31602) has part fentanyl (CHEBI:119915)
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
INNs Sources
fentanila ChemIDplus
fentanyl ChemIDplus
fentanylum ChemIDplus
Synonyms Sources
1-phenethyl-4-(N-phenylpropionamido)piperidine ChemIDplus
1-phenethyl-4-N-propionylanilinopiperidine ChemIDplus
FENTANYL ChEMBL
N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide ChemIDplus
N-(1-phenethyl-4-piperidyl)propionanilide ChemIDplus
N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide ChEMBL
N-(1-phenethylpiperidin-4-yl)-N-phenylpropionamide ChEMBL
N-phenethyl-4-(N-propionylanilino)piperidine ChemIDplus
N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide ChemIDplus
Database Links Databases
D00320 KEGG DRUG
DB00813 DrugBank
Fentanyl Wikipedia
FR1344366 Patent
US3164600 Patent
View more database links
Registry Numbers Types Sources
437-38-7 CAS Registry Number ChemIDplus
437-38-7 CAS Registry Number KEGG DRUG
494484 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10669565 PubMed citation ChEMBL
10987438 PubMed citation ChEMBL
11585443 PubMed citation ChEMBL
14698188 PubMed citation ChEMBL
16621415 PubMed citation Europe PMC
Last Modified
06 March 2014
General Comment
2011-03-17 A μ-opioid receptor agonist, fentanyl is a potent opioid analgesic used (often as the citric acid salt) in the management of labour pain, postoperative pain, and chronic intractable cancer pain. It is also widely used as the analgesic component of balanced anaesthesia.