OXYCODONE

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Synonyms
Status
Molecule Category Free-form
ATC N02AA05
UNII CD35PMG570
EPA CompTox DTXSID5023407

Structure

InChI Key BRUQQQPBMZOVGD-XFKAJCMBSA-N
Smiles COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
InChI
InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H21NO4
Molecular Weight 315.37
AlogP 1.05
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 59.0
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 23.0

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 Hydrolase
- 76200 - - 80
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
17-500 - - 12-12 47
Assay Description Organism Bioactivity Reference
Displacement of [3H]DAMGO from mu opioid receptor of rat brain membranes Rattus norvegicus 43.6 nM
Inhibition of electric eel AChE at 500 uM by Ellman's method Electrophorus electricus 80.0 %
Activation of mouse KOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay relative to U69593 Mus musculus 59.0 %
Activation of mouse MOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay relative to DAMGO Mus musculus 97.0 %
Activation of human KOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay relative to U69593 Homo sapiens 47.0 %
Activation of human DOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay relative to DPDPE Homo sapiens 93.0 %
Activation of human MOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay relative to DAMGO Homo sapiens 93.0 %
Agonist activity at mouse MOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay Mus musculus 160.0 nM
Agonist activity at human MOR assessed as inhibition of forskolin-stimulated cAMP accumulation after 30 mins by cell based TR-FRET assay Homo sapiens 500.0 nM
Scintillation Proximity Assay (SPA): Briefly, serial dilutions of the test compounds were placed in a 96-well plate to which were added SPA beads, membrane and radioligand. The assay conditions for each opioid receptor subtype are described in Table 10 below. The plates were incubated for 8 hours-overnight at room temperature, spun at 1000 rpm to pellet the SPA beads, and radioactivity was measured using the TopCount microplate Scintillation counter. Specific binding at each concentration of test compound was calculated by subtracting the non-specific binding measured in the presence of excess cold ligand. IC50 values were obtained by non-linear regression of specific binding versus concentration curves and Ki values were calculated using Kd values that were experimentally pre-determined for each lot of membrane preparations. Homo sapiens 133.48 nM
HiRange Homogenous Time-Resolved Fluorescence (HTRF) Assay: Briefly, suspensions of cells expressing either the mu, kappa or delta opioid receptors were prepared in buffer containing 0.5 mM isobutyl-methyl xanthine (IBMX). Cells were incubated with varying concentrations of PEG-opioid conjugates and 3 uM forskolin for 30 minutes at room temperature. cAMP was detected following a two-step assay protocol per the manufacturer's instructions and time resolved fluorescence was measured with the following settings: 330 nm excitation; 620 nm and 665 nm emission; 380 nm dichroic mirror. The 665 nm/620 nm ratio is expressed as Delta F % and test compound-related data is expressed as a percentage of average maximum response in wells without forskolin. EC50 values were calculated for each compound from a sigmoidal dose-response plot of concentrations versus maximum response. Homo sapiens 478.0 nM
Displacement of [3H]-DAMGO from human MOR expressed in CHOK1 cell membranes incubated for 60 mins by liquid scintillation counting method Homo sapiens 12.0 nM
Agonist activity at human MOR expressed in CHOK1 cells assessed as stimulation of cAMP accumulation incubated for 45 mins by HTRF assay Homo sapiens 17.0 nM
Displacement of [3H]-(+)-pentazocine from human sigma-1 receptor expressed in HEK293 membranes at 10 uM incubated for 120 mins by liquid scintillation counting method relative to control Homo sapiens 50.0 %
Displacement of [3H]DAMGO from MOR in Wistar rat brain membranes after 60 mins by liquid scintillation analysis Rattus norvegicus 8.9 nM
Displacement of [3H]Ile5,6-deltorphin-2 from DOR in Wistar rat brain membranes after 60 mins by liquid scintillation analysis Rattus norvegicus 487.0 nM
Displacement of [3H]HS-665 from KOR in guinea pig brain membranes after 60 mins by liquid scintillation analysis Cavia porcellus 325.0 nM
Agonist activity at MOR/CB1R/CB2R receptor in Wistar rat brain membranes after 60 mins by [35S]-GTPgammaS binding assay Rattus norvegicus 51.0 nM
Agonist activity at MOR in Wistar rat brain membranes after 60 mins by [35S]-GTPgammaS binding assay Rattus norvegicus 25.0 nM
Antinociceptive activity in CD1 mouse PSNL model assessed as reduction in mechanical allodynia by measuring decrease in the pressure required to elicit withdrawal of the ipsilateral paw after von Frey filament stimulation at 1.25 mg/kg, ip BID for 11 days from day 13 to day 22 Mus musculus 51.0 %
Displacement of 3H](+)-pentazocine from human sigma1 receptor expressed in HEK293 cell membranes at 10 uM incubated for 120 mins by liquid scintillation counting method Homo sapiens 50.0 %
Inhibition of human ERG expressed in CHO cells at 10 uM at -80 mV holding potential by whole cell patch clamp assay Homo sapiens 50.0 %
Agonist activity at human MOR expressed in CHOK1 cells assessed as stimulation of cAMP accumulation incubated for 45 mins by HTRF assay Homo sapiens 17.0 nM
Displacement of [3H]-DAMGO from human MOR expressed in CHOK1 cell membranes incubated for 60 mins by liquid scintillation counting method Homo sapiens 12.0 nM
Displacement of [3H]-DAMGO from human MOR expressed in CHO-K1 cell membranes incubated for 60 mins measured by MicroBeta scintillation counter method Homo sapiens 12.0 nM
Agonist activity at human MOR expressed in CHO-K1 cells assessed as reduction in forskolin-induced cAMP production incubated for 45 mins by by HTRF assay Homo sapiens 17.0 nM

Environmental Exposure

Environmental Exposure Map
Countries
Czech Republic
Germany
Serbia
Slovenia
USA

Cross References

Resources Reference
ChEBI 7852
ChEMBL CHEMBL656
DrugBank DB00497
DrugCentral 2029
FDA SRS CD35PMG570
Human Metabolome Database HMDB0014640
Guide to Pharmacology 7093
KEGG C08018
PharmGKB PA450741
SureChEMBL SCHEMBL2737
ZINC ZINC000000403533
CONTENTS