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Compound Detail

CHEMBL656

OXYCODONE
💊 Approved Drug
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💊 Approved Drug
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL656
Name OXYCODONE
Phase Approved
Structure Type MOL
InChI Key BRUQQQPBMZOVGD-XFKAJCMBSA-N
Therapeutic ✓ Yes

Known Names

(-)-14-hydroxydihydrocodeinone 14-hydroxydihydrocodeinone Dihydrone IDS-NO-002 N02AA05 NSC-19043 Oxicodona Oxicone Oxycodone Oxycodone cii Oxymorphone 3-methyl ether Pavinal +7 more
11
Targets
23
Activities
3
Assay Types
11
PK Parameters
20
Publications
19
Known Names
20
Indications
1
Mechanisms

Molecular Properties

315.4
MW (Da)
1.05
ALogP
5
HBA
1
HBD
59.0
PSA (Ų)
0.84
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1950
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product
USAN Year 1963

Extended Properties

Molecular Formula C18H21NO4
MW 315.37
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness 1.91

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mu opioid receptor agonist AGONIST Mu-type opioid receptor ✓ ✓

Indications

Chronic Pain Pain Substance-Related Disorders Substance-Related Disorders Back Pain Cancer Pain Diabetic Neuropathies Diabetic Neuropathies Genital Neoplasms, Female Hypospadias Joint Diseases Kidney Calculi Low Back Pain Neck Pain Neoplasms Osteoarthritis Osteoarthritis, Hip Osteoarthritis, Knee Parkinson Disease Pruritus

ATC Classification

N02AA05
oxycodone
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
misuse
Country: United States

Activity Summary

EC50 11 meas. best 7.77
Ki 10 meas. best 8.05
IC50 2 meas. best 4.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL270
 Ki 8.05 7.705 8.9 2
Mu-type opioid receptor
CHEMBL233
 Ki 7.92 7.66 12.0 4
Mu-type opioid receptor
CHEMBL233
 EC50 7.77 7.186 17.0 5
Mu-type opioid receptor
CHEMBL270
 EC50 7.6 7.6 25.0 1
Unchecked
CHEMBL612545
 EC50 7.29 7.29 51.0 1
Mu-type opioid receptor
CHEMBL2858
 EC50 6.8 6.8 160.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 6.49 6.49 325.0 1
Delta-type opioid receptor
CHEMBL269
 Ki 6.31 6.135 487.0 2
Kappa-type opioid receptor
CHEMBL3614
 Ki 5.58 5.58 2658.0 1
Delta-type opioid receptor
CHEMBL236
 EC50 5.4 5.4 4000.0 1
Kappa-type opioid receptor
CHEMBL237
 EC50 4.8 4.8 16000.0 1
Kappa-type opioid receptor
CHEMBL4329
 EC50 4.8 4.8 16000.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 4.12 4.12 76200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6.1 mL.min-1.kg-1 Homo sapiens
CL 6.1 mL.min-1.kg-1 Homo sapiens
Cmax 50.0 nM Homo sapiens
Cmax 50.0 nM Homo sapiens
Fu 0.55 - Homo sapiens
Fu 0.55 - Homo sapiens
Fu 0.87 - Rattus norvegicus
Fu 0.66 - Rattus norvegicus
MRT 6.8 hr Homo sapiens
T1/2 5.5 hr Homo sapiens
Vd 4.2 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 8.9 nM 8.05 Displacement of [3H]DAMGO from MOR in Wistar rat brain membranes after 60 mins b... 31220675
Mu-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]-DAMGO from human MOR expressed in CHO-K1 cell membranes inc... 34236190
Mu-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]-DAMGO from human MOR expressed in CHOK1 cell membranes incu... 33064947
Mu-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]-DAMGO from human MOR expressed in CHOK1 cell membranes incu... 31743642
Mu-type opioid receptor EC50 = 17.0 nM 7.77 Agonist activity at human MOR expressed in CHOK1 cells assessed as stimulation o... 33064947
Mu-type opioid receptor EC50 = 17.0 nM 7.77 Agonist activity at human MOR expressed in CHO-K1 cells assessed as reduction in... 34236190
Mu-type opioid receptor EC50 = 17.0 nM 7.77 Agonist activity at human MOR expressed in CHOK1 cells assessed as stimulation o... 31743642
Mu-type opioid receptor EC50 = 25.0 nM 7.6 Agonist activity at MOR in Wistar rat brain membranes after 60 mins by [35S]-GTP... 31220675
Mu-type opioid receptor Ki = 43.6 nM 7.36 Displacement of [3H]DAMGO from mu opioid receptor of rat brain membranes 16033285
Unchecked EC50 = 51.0 nM 7.29 Agonist activity at MOR/CB1R/CB2R receptor in Wistar rat brain membranes after 6... 31220675
Mu-type opioid receptor Ki = 133.48 nM 6.88 Scintillation Proximity Assay (SPA): Briefly, serial dilutions of the test compo... -
Mu-type opioid receptor EC50 = 160.0 nM 6.8 Agonist activity at mouse MOR assessed as inhibition of forskolin-stimulated cAM... 23880538
Kappa-type opioid receptor Ki = 325.0 nM 6.49 Displacement of [3H]HS-665 from KOR in guinea pig brain membranes after 60 mins ... 31220675
Mu-type opioid receptor EC50 = 478.0 nM 6.32 HiRange Homogenous Time-Resolved Fluorescence (HTRF) Assay: Briefly, suspensions... -
Delta-type opioid receptor Ki = 487.0 nM 6.31 Displacement of [3H]Ile5,6-deltorphin-2 from DOR in Wistar rat brain membranes a... 31220675
Mu-type opioid receptor EC50 = 500.0 nM 6.3 Agonist activity at human MOR assessed as inhibition of forskolin-stimulated cAM... 23880538
Delta-type opioid receptor Ki = 1087.0 nM 5.96 Displacement of [3H[Ile5,6]-deltorphin II from delta opioid receptor of rat brai... 16033285
Kappa-type opioid receptor Ki = 2658.0 nM 5.58 Displacement of [3H]U-69593 from kappa opioid receptor of rat brain membranes 16033285
Delta-type opioid receptor EC50 = 4000.0 nM 5.4 Agonist activity at human DOR assessed as inhibition of forskolin-stimulated cAM... 23880538
Kappa-type opioid receptor EC50 = 16000.0 nM 4.8 Agonist activity at human KOR assessed as inhibition of forskolin-stimulated cAM... 23880538

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
25868745 10.1016/j.bmc.2015.03.049 Mus musculus 8
31597043 10.1021/acs.jmedchem.9b01301 ADMET 6
31597043 10.1021/acs.jmedchem.9b01301 Unchecked 4
31597043 10.1021/acs.jmedchem.9b01301 Solute carrier family 22 member 1 4
18426954 10.1124/dmd.108.020479 ADMET 4
23880538 10.1016/j.bmcl.2013.06.084 Kappa-type opioid receptor 4
34236190 10.1021/acs.jmedchem.1c00417 Mus musculus 4
31220675 10.1016/j.ejmech.2019.05.037 Unchecked 4
31220675 10.1016/j.ejmech.2019.05.037 Rattus norvegicus 4
23880538 10.1016/j.bmcl.2013.06.084 Mu-type opioid receptor 4
34236190 10.1021/acs.jmedchem.1c00417 Mu-type opioid receptor 3
31743642 10.1021/acs.jmedchem.9b01256 Mu-type opioid receptor 3
19764786 10.1021/jm901036q Plasma 3
31220675 10.1016/j.ejmech.2019.05.037 Mu-type opioid receptor 3
23439660 10.1124/dmd.112.050401 Nuclear receptor subfamily 1 group I member 3 3
16033285 10.1021/jm0580205 Mus musculus 3
33064947 10.1021/acs.jmedchem.0c01127 Mu-type opioid receptor 3
21149540 10.1124/dmd.110.035998 Brain 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3

Data from ChEMBL 36 via Core Engine