fentanyl (CHEBI:119915)

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ChEBI Name	fentanyl

ChEBI ID	CHEBI:119915

Definition	A monocarboxylic acid amide 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

Average Mass

336.47050

Monoisotopic Mass

336.22016

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.

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

Synonyms	Sources
1-phenethyl-4-(N-phenylpropionamido)piperidine	ChemIDplus
1-phenethyl-4-N-propionylanilinopiperidine	ChemIDplus
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
phentanyl	DrugBank

Brand Name	Source
Duragesic	ChemIDplus

Last Modified

29 October 2018

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.