CHEBI:31602 - fentanyl citrate

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ChEBI Name fentanyl citrate
ChEBI ID CHEBI:31602
Definition The citric acid salt of fentanyl, comprising equimolar amounts of citric acid and fentanyl. A μ-opioid receptor agonist, it is a potent opioid analgesic used 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:130072
Supplier Information
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Formula C28H36N2O8
Net Charge 0
Average Mass 528.59400
Monoisotopic Mass 528.24717
InChI InChI=1S/C22H28N2O.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKey IVLVTNPOHDFFCJ-UHFFFAOYSA-N
SMILES OC(=O)CC(O)(CC(O)=O)C(O)=O.CCC(=O)N(C1CCN(CC1)CCc1ccccc1)c1ccccc1
Roles Classification
Biological Role(s): mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
Application(s): mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fentanyl citrate (CHEBI:31602) has part fentanyl (CHEBI:119915)
fentanyl citrate (CHEBI:31602) has role μ-opioid receptor agonist (CHEBI:55322)
fentanyl citrate (CHEBI:31602) has role opioid analgesic (CHEBI:35482)
fentanyl citrate (CHEBI:31602) is a citrate salt (CHEBI:50744)
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide 2-hydroxypropane-1,2,3-tricarboxylate
Synonyms Sources
fentanyl citrate ChemIDplus
fentanyl dihydrogen citrate ChemIDplus
fentanyl monocitrate ChEBI
N-(1-phenethyl-4-piperidinyl)propionanilide dihydrogen citrate ChemIDplus
N-(1-phenethyl-4-piperidyl)propionanilide citrate ChemIDplus
N-(1-phenethyl-4-piperidyl)propionanilide dihydrogen citrate ChemIDplus
N-(1-phenethylpiperidin-4-yl)-N-phenylpropionamide citrate ChEBI
N-phenyl-N-[1-(2-phenylethyl)-4-piperidyl]propanamide citrate ChEBI
phentanyl citrate ChemIDplus
Brand Names Sources
Abstral ChemIDplus
Actiq ChemIDplus
Fentora ChemIDplus
Lazanda ChemIDplus
Leptanal ChemIDplus
Onsolis ChemIDplus
Oralet KEGG DRUG
Manual Xrefs Databases
D01399 KEGG DRUG
DBSALT000301 DrugBank
View more database links
Registry Numbers Types Sources
4121500 Reaxys Registry Number Reaxys
990-73-8 CAS Registry Number ChemIDplus
990-73-8 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
11448232 PubMed citation ChEMBL
26706627 PubMed citation Europe PMC
29284838 PubMed citation Europe PMC
6481762 PubMed citation ChEMBL
Last Modified
29 October 2018