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CHEBI:31602 - fentanyl citrate

ChEBI IDCHEBI:31602
ChEBI Namefentanyl citrate
Stars
DefinitionThe 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.
Secondary ChEBI IDCHEBI:130072
Last Modified29 October 2018
DownloadsMolfile
FormulaC22H28N2O.C6H8O7
Net Charge0
Average Mass528.602
Monoisotopic Mass528.24717
SMILESCCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1.O=C(O)CC(O)(CC(=O)O)C(=O)O
InChIInChI=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)
InChIKeyIVLVTNPOHDFFCJ-UHFFFAOYSA-N
Roles Classification
Biological Roles:
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 μ-opioid receptor.
Applications:
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 μ-opioid receptor.
ChEBI Ontology
Outgoing Relation(s)
fentanyl citrate (CHEBI:31602) has part fentanyl (CHEBI:119915)
fentanyl citrate (CHEBI:31602) has role opioid analgesic (CHEBI:35482)
fentanyl citrate (CHEBI:31602) has role μ-opioid receptor agonist (CHEBI:55322)
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  Source
fentanyl citrateChemIDplus
N-(1-phenethyl-4-piperidinyl)propionanilide dihydrogen citrateChemIDplus
phentanyl citrateChemIDplus
fentanyl dihydrogen citrateChemIDplus
N-(1-phenethyl-4-piperidyl)propionanilide citrateChemIDplus
N-(1-phenethyl-4-piperidyl)propionanilide dihydrogen citrateChemIDplus
Brand Names  Source
FentoraChemIDplus
AbstralChemIDplus
ActiqChemIDplus
LazandaChemIDplus
OnsolisChemIDplus
LeptanalChemIDplus
Manual XrefsDatabases
D01399KEGG DRUG
DBSALT000301DrugBank
Registry NumbersSources
Reaxys:4121500Reaxys
CAS:990-73-8KEGG DRUG
CAS:990-73-8ChemIDplus
Citations