FENTANYL

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N01AH01 N02AB03
UNII UF599785JZ
EPA CompTox DTXSID9023049

Structure

InChI Key PJMPHNIQZUBGLI-UHFFFAOYSA-N
Smiles CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H28N2O
Molecular Weight 336.48
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(%)
Enzyme Oxidoreductase
- - - 5462 -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 1820 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
1-53 3-3400 - 2-570 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 19953 - - -
Membrane receptor
1-53 3-3400 - 2-570 -
Other membrane protein
- 4973 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
31600-31600 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 46170 - - 74
Assay Description Organism Bioactivity Reference
Compound was tested in vitro for binding affinity towards delta opioid receptor by measuring displacement of [3H]DPDPE from guinea pig brain membranes Cavia porcellus 187.0 nM
Inhibition of electrically evoked contraction in guinea pig ileum determined in vitro Cavia porcellus 1.76 nM
Inhibition of opioid activity in electricaly stimulated myenteric plexus longitudinal muscle of guinea pig ileum(GPI) preparation Cavia porcellus 3.45 nM
Inhibition of the electrically induced muscle contractions was determined using the guinea pig ileum Cavia porcellus 4.5 nM
Inhibition of opioid activity in electricaly stimulated myenteric plexus longitudinal muscle of mouse vas deferens(MVD) preparation Mus musculus 9.45 nM
Inhibition of the electrically induced muscle contractions was determined using the mouse vas deferens Mus musculus 490.0 nM
Compound was tested in vitro for binding affinity towards mu opioid receptor by measuring displacement of [3H]DAGO from guinea pig brain membranes Cavia porcellus 3.1 nM
Binding affinity against delta-opiate receptor (human) using [3H]-DPDPE radioligand None 431.0 nM
Binding affinity against Opioid receptor kappa 1 None 196.5 nM
In vitro binding activity against opioid receptor mu using [3H]-DAGO as radioligand Cavia porcellus 3.1 nM
In vivo binding affinity to opioid receptor preparations from rat brain None 25.0 nM
In vitro binding activity against opioid receptor delta using [3DPDPE] as radioligand Cavia porcellus 187.4 nM
Binding affinity towards Opioid receptor kappa 1 using [3H]U-69593 as radioligand. Cavia porcellus 196.5 nM
Binding affinity of compound evaluated for Opioid receptor delta 1 isolated from rat brain None 400.0 nM
Binding affinity against Opioid receptor delta 1 in guinea pig brain membranes Cavia porcellus 679.0 nM
Displacement of [3H]naloxone from rat brain Opioid receptors Rattus norvegicus 8.0 nM
Binding affinity to opioid receptors by the displacement of [3H]fentanyl in rat brain homogenates None 1.14 nM
Displacement of [3H]nalotrexone from rat-brain Opioid receptors Rattus norvegicus 25.0 nM
Displacement [3H]naloxone from rat-brain Opioid receptors Rattus norvegicus 1.6 nM
In vitro affinity to displace [3H]naloxone from opiate receptor in freshly prepared rat brain homogenates None 2.16 nM
Displacement of [3H]DAMGO (2 nM ) from opioid receptor mu 1 in human brain Homo sapiens 2.9 nM
Binding affinity against Opioid receptor mu 1 None 3.97 nM
Ability to displace [3H]naloxone from the Opioid receptor mu 1 isolated from the rat brain membranes. None 2.16 nM
Inhibition of [3H]DAMGO binding to mu opioid receptor of rat brain membranes None 1.5 nM
Binding affinity towards Opioid receptor mu 1 using [3H]DAMGO as radioligand. None 3.97 nM
Displacement [3H]-naloxone from the Opioid receptor mu 1 isolated from rat brain membrane. None 2.16 nM
Binding affinity against mu-opiate receptor (human) using [3H]DAMGO radioligand None 1.3 nM
Binding affinity against mu opioid receptor in guinea pig brain membranes Cavia porcellus 8.45 nM
Compound was tested for its ability to stimulate [35S]GTP-gamma-S, binding to membranes from C6 glioma cells stably expressing rat mu opioid receptor None 32.4 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 73.6 %
Agonist activity at mu opioid receptor in guinea pig ileum assessed as inhibition of electrically-stimulated muscle contraction Cavia porcellus 3.45 nM
Agonist activity at delta opioid receptor in mouse vas deferens assessed as inhibition of electrically-stimulated muscle contraction Mus musculus 9.45 nM
Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane Rattus norvegicus 5.9 nM
Displacement of [3H]DSLET from delta opioid receptor in rat brain membrane Rattus norvegicus 568.0 nM
Displacement of [3H]U69593 from kappa opioid receptor in guinea pig brain membrane Cavia porcellus 298.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens -53.3 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 22.6 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 11.7 %
Analgesic activity in ip dosed Swiss albino Mus musculus (mouse) assessed as decrease in time spent in formalin-induced paw licking administered 30 min prior to formalin injection measured after 15 to 30 min (late phase) Mus musculus 78.0 %
Inhibition of delta opioid receptor in mouse vas deferens assessed as inhibition of electrically-stimulated muscle contraction Mus musculus 9.4 nM
Inhibition of mu opioid receptor in guinea pig ileum assessed as inhibition of electrically-stimulated muscle contraction Cavia porcellus 3.4 nM
Displacement of [3H]-DAMGO from Swiss Webster mouse neural membranes mu opioid receptor after 60 mins by liquid scintillation spectrometric analysis Mus musculus 5.9 nM
Displacement of [3H]-DPDPE from Swiss Webster mouse neural membranes delta opioid receptor after 60 mins by liquid scintillation spectrometric analysis Mus musculus 568.0 nM
Agonist activity at delta opioid receptor in beta-funaltrexamine-treated mouse vas deferens Mus musculus 3.45 nM
Agonist activity at mu opioid receptor in beta-funaltrexamine-treated guinea pig isolated ileum Cavia porcellus 9.45 nM
Displacement of [3H] DAMGO from rat mu-opioid receptor Rattus norvegicus 570.0 nM
Agonist activity at delta opioid receptor in mouse vas deferens assessed as inhibition of electrically stimulated muscle contraction Mus musculus 9.5 nM
Agonist activity at mu opioid receptor in guinea pig ileum assessed as inhibition of electrically stimulated muscle contraction Cavia porcellus 3.4 nM
Displacement of [3H]DPDPE from human delta opioid receptor Homo sapiens 570.0 nM
Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes Rattus norvegicus 5.9 nM
Agonist activity at Gi-coupled mu opioid receptor (unknown origin) expressed in HEK293T cells assessed as inhibition of cAMP production at pH 7.4 measured after 15 mins by Glo-Sensor assay Homo sapiens 10.72 nM
Agonist activity at Gi-coupled mu opioid receptor (unknown origin) expressed in HEK293T cells assessed as inhibition of cAMP production at pH 6.5 measured after 15 mins by Glo-Sensor assay Homo sapiens 5.495 nM
Binding affinity to mu opioid receptor (unknown origin) expressed in HEK cells at pH 7.4 Homo sapiens 1.1 nM
Agonist activity at human mu opioid receptor expressed in CHO cell membranes after 1 hr by [35S]-GTPgammaS binding assay Homo sapiens 43.0 nM
Agonist activity at human mu opioid receptor expressed in human U2OS cells co-transfected with beta-arrestin-2 assessed as increase in beta-arrestin-2 recruitment after 90 mins by BRET assay Homo sapiens 53.0 nM
Displacement of [3H]PPP from sigma1 receptor (unknown origin) Homo sapiens 354.0 nM
Displacement of [3H]DAMGO from rat brain mu opioid receptor incubated for 60 mins by microbeta scintillation counting method Rattus norvegicus 1.23 nM
Agonist activity at human MOR expressed in CHO-K1 cells assessed as cAMP accumulation incubated for 30 mins and measured after 1 hr by Eu-cAMP tracer based TR-FRET assay Homo sapiens 0.51 nM
Agonist activity at mu opioid receptor (unknown origin) expressed in HEK293-A cells assessed as inhibition of forskolin-stimulated cAMP accumulation incubated for 30 mins by competition PKA binding assay Homo sapiens 17.2 nM Agonist activity at mu opioid receptor (unknown origin) expressed in HEK293-A cells assessed as inhibition of forskolin-stimulated cAMP accumulation incubated for 30 mins by competition PKA binding assay Homo sapiens 17.38 nM
Inhibition of sigma 1 receptor (unknown origin) Homo sapiens 0.39 nM
Displacement of [3H]DAMGO from human mu opioid receptor expressed in HEK293 cell membrane incubated for 60 mins by radioligand binding assay Homo sapiens 5.23 nM
Displacement of [3H]-N-methylspiperone from human dopamine D4 receptor expressed in HEK293 cell membranes incubated for 60 mins by microbeta scintillation counting analysis Homo sapiens 554.0 nM

Environmental Exposure

Environmental Exposure Map
Countries
Czech Republic
Germany
Slovenia

Cross References

Resources Reference
ChEBI 119915
ChEMBL CHEMBL596
DrugBank DB00813
DrugCentral 1164
FDA SRS UF599785JZ
Human Metabolome Database HMDB0014951
Guide to Pharmacology 1626
PDB 7V7
PharmGKB PA449599
PubChem 3345
SureChEMBL SCHEMBL8804
ZINC ZINC000002522669
CONTENTS