Compound Detail

CHEMBL963

OXYMORPHONE

💊 Approved Drug

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💊 Approved Drug

CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL963
Name	OXYMORPHONE
Phase	Approved
Structure Type	MOL
InChI Key	UQCNKQCJZOAFTQ-ISWURRPUSA-N
Therapeutic	✓ Yes

Known Names

14-hydroxydihydromorphinone 7,8-dihydro-14-hydroxymorphinone Dihydroxymorphinone IDS-NO-003 NIH 10323 NSC-19045 Oximorfona Oxycodone hydrochloride impurity, oxymorphone- Oxymorphone Oxymorphone cii

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

301.3

MW (Da)

0.75

ALogP

HBA

HBD

70.0

PSA (Å²)

0.74

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1959
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula	C17H19NO4
MW	301.34
Aromatic Rings	1
Heavy Atoms	22
NP-Likeness	2.20

Indications

Pain Chronic Pain

ATC Classification

N02AA11

oxymorphone

Level 1: NERVOUS SYSTEM

Level 2: ANALGESICS

Activity Summary

Ki 27 meas. best 9.27

IC50 9 meas. best 10.89

EC50 2 meas. best 9.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Opioid receptor CHEMBL2094129	IC50	10.89	10.355	0.0	2
Mu-type opioid receptor CHEMBL4354	Ki	9.27	8.7333	0.5	3
Mu-type opioid receptor CHEMBL270	Ki	9.01	7.9975	1.0	4
Opioid receptor CHEMBL2094129	EC50	9.0	9.0	1.0	1
Mu-type opioid receptor CHEMBL4354	IC50	8.85	8.85	1.4	1
Mu-type opioid receptor CHEMBL233	Ki	8.75	8.75	1.8	1
Opioid receptors; mu and delta CHEMBL2221343	Ki	8.33	7.31	4.7	2
Mu-type opioid receptor CHEMBL2858	Ki	8.3	8.3	5.0	1
Mu-type opioid receptor CHEMBL233	EC50	8.11	8.11	7.8	1
Cavia porcellus CHEMBL369	IC50	7.62	7.62	24.0	1
Kappa-type opioid receptor CHEMBL237	Ki	7.6	7.6	25.3	1
Unchecked CHEMBL612545	Ki	7.37	7.37	42.7	1
Delta-type opioid receptor CHEMBL236	IC50	7.35	7.35	45.0	1
Delta-type opioid receptor CHEMBL236	Ki	7.3	7.1	50.0	3
Kappa-type opioid receptor CHEMBL3952	Ki	7.24	6.8625	57.6	4
Mus musculus CHEMBL375	IC50	7.11	7.11	77.0	1
Delta-type opioid receptor CHEMBL269	Ki	7.09	7.09	80.5	1
Opioid receptors; mu/kappa/delta CHEMBL2095181	IC50	7.05	7.05	90.0	1
Kappa-type opioid receptor CHEMBL3614	Ki	7.02	6.6867	95.0	3
Delta-type opioid receptor CHEMBL3222	Ki	6.21	6.1633	610.0	3
Kappa-type opioid receptor CHEMBL3952	IC50	6.2	6.2	630.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Fu	0.73	-	Rattus norvegicus
Fu	0.75	-	Rattus norvegicus
Ke	11.2	nM	Sus scrofa
Vd	4.0	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Opioid receptor	IC50	=	0.013	nM	10.89	Concentration for 50% inhibition of [3H]naloxone (1 M) binding to opioid recepto...	6094809
Opioid receptor	IC50	=	0.15	nM	9.82	Concentration for 50% inhibition of [3H]naloxone (1 M) binding to opioid recepto...	6094809
Mu-type opioid receptor	Ki	=	0.54	nM	9.27	Displacement of [3H]DAMGO from mu opioid receptor in guinea pig forebrain homoge...	21641798
Mu-type opioid receptor	Ki	=	0.78	nM	9.11	Inhibitory binding constant in guinea pig brain homogenate was reported at mu si...	2409281
Mu-type opioid receptor	Ki	=	0.97	nM	9.01	Inhibition of [3H]DAMGO binding to opioid receptor mu from rat brain membranes	15857143
Opioid receptor	EC50	=	1.0	nM	9.0	Binding affinity to rat brain opioid receptor	73588
Mu-type opioid receptor	IC50	=	1.4	nM	8.85	Inhibition of opioid receptor mu by displacing 1 nM [3H]DAGO in guinea pig brain...	1335078
Mu-type opioid receptor	Ki	=	1.79	nM	8.75	Displacement of [3H]-DAMGO from recombinant human MOR expressed in CHO cell memb...	29053268
Opioid receptors; mu and delta	Ki	=	4.677	nM	8.33	Displacement of [3H]-DAMGO from mouse MOR/DOR expressed in HEK293 cells	23585918
Mu-type opioid receptor	Ki	=	5.012	nM	8.3	Displacement of [3H]-DAMGO from mouse MOR expressed in HEK293 cells	23585918
Mu-type opioid receptor	EC50	=	7.8	nM	8.11	Agonist activity at recombinant human MOR expressed in CHO cell membranes after ...	29053268
Mu-type opioid receptor	Ki	=	15.0	nM	7.82	Binding affinity against Opioid receptor mu 1 of guinea pig brain membranes usin...	2879914
Mu-type opioid receptor	Ki	=	17.4	nM	7.76	Displacement of [3H]- diprenorphine from mu-receptor expressed in HEK 293 cells	11300867
Mu-type opioid receptor	Ki	=	23.1	nM	7.64	Displacement of [3H]- diprenorphine from mu-W318A-receptor expressed in HEK 293	11300867
Cavia porcellus	IC50	=	24.0	nM	7.62	Agonist activity in the guinea pig ileum longitudinal muscle myenteric plexus.	2409281
Kappa-type opioid receptor	Ki	=	25.3	nM	7.6	Displacement of [3H]-HS665 from recombinant human KOR expressed in CHO cell memb...	29053268
Mu-type opioid receptor	Ki	=	26.2	nM	7.58	Displacement of [3H]- diprenorphine from mu-K303E-receptor expressed in HEK 293	11300867
Unchecked	Ki	=	42.7	nM	7.37	Displacement of [3H]NTI from delta opioid receptor in guinea pig forebrain homog...	21641798
Delta-type opioid receptor	IC50	=	45.0	nM	7.35	Inhibition of Opioid receptor delta 1 by displacing 1 nM [3H]DPDPE in guinea pig...	1335078
Delta-type opioid receptor	Ki	=	50.0	nM	7.3	Inhibitory binding constant in guinea pig brain homogenate was reported at Opioi...	2409281

Literature References

PubMed	DOI	Target Context	# Activities
29053268	10.1021/acs.jmedchem.7b01363	Mu-type opioid receptor	5
31597043	10.1021/acs.jmedchem.9b01301	Solute carrier family 22 member 1	5
29053268	10.1021/acs.jmedchem.7b01363	Mus musculus	4
20014752	10.1021/tx900326k	Hepatotoxicity	3
6094809	10.1021/jm00378a009	Opioid receptor	3
11300867	10.1021/jm000381r	Kappa-type opioid receptor	3
11300867	10.1021/jm000381r	Mu-type opioid receptor	3
19764786	10.1021/jm901036q	Plasma	3
10836148	10.1146/annurev.pharmtox.40.1.581	UDP-glucuronosyltransferase 2B7	3
21149540	10.1124/dmd.110.035998	Brain	3
23439660	10.1124/dmd.112.050401	Nuclear receptor subfamily 1 group I member 2	2
23439660	10.1124/dmd.112.050401	Nuclear receptor subfamily 1 group I member 3	2
22931300	10.1021/tx300075j	Cytochrome P450 3A4	2
11300867	10.1021/jm000381r	Delta-type opioid receptor	2
26948801	10.1016/j.drudis.2016.02.015	Homo sapiens	2
22931300	10.1021/tx300075j	Liver microsomes	2
73588	10.1021/jm00199a018	Rattus norvegicus	2
73588	10.1021/jm00199a018	Unchecked	2
23585918	10.1021/ml300083p	Opioid receptors; mu and delta	2
21641798	10.1016/j.bmcl.2011.04.147	Unchecked	2

Data from ChEMBL 36 via Core Engine