FENTANYL CITRATE

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Search structure


Trade Names	ABSTRAL ACTIQ FENTANYL FENTANYL CITRATE FENTANYL CITRATE PRESERVATIVE FREE FENTORA LAZANDA ONSOLIS SUBLIMAZE PRESERVATIVE FREE
Synonyms	Abstral Actiq Fentanyl Fentanyl buccal Fentanyl citrate Fentanyl citrate cii Fentanyl citrate preservative free Fentora Instanyl Kw-2246 Lazanda Leptanal MCN-JR-4263-49 Onsolis R-4263 Sublimaze Sublimaze preservative free Thalamonal
Status
Molecule Category	Salt-form
UNII	MUN5LYG46H
EPA CompTox	DTXSID80243933
Parent Compound:	FENTANYL


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	IVLVTNPOHDFFCJ-UHFFFAOYSA-N
Smiles	CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1.O=C(O)CC(O)(CC(=O)O)C(=O)O
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C28H36N2O8
Molecular Weight	528.6
AlogP	4.14
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	6.0
Polar Surface Area	23.55
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	25.0

Bioactivity

Mechanism of Action	Action	Reference
Mu opioid receptor agonist	AGONIST	DailyMed


Protein: Mu opioid receptor Description: Mu-type opioid receptor Organism : Homo sapiens P35372 ENSG00000112038

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor	-	2	-	-	-

Assay Description	Organism	Bioactivity	Reference
Agonist activity at mu opioid receptor in Hartley guinea pig ileum/longitudinal muscle with myenteric plexus assessed as inhibition of PL-017-induced GPI contraction height	Cavia porcellus	1.9 nM
Agonist activity at delta opioid receptor in ICR mouse vas deferens assessed as inhibition of MVD contraction height	Mus musculus	7.2 nM

Cross References

Resources	Reference
ChEBI	31602
ChEMBL	CHEMBL688
FDA SRS	MUN5LYG46H
Guide to Pharmacology	1626
KEGG	D00320
PubChem	13810
SureChEMBL	SCHEMBL40733
ZINC	ZINC02522669

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).