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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO4
Molecular Weight 301.3371
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYMORPHONE

SMILES

CN1CC[C@@]23[C@H]4OC5=C2C(C[C@@H]1[C@]3(O)CCC4=O)=CC=C5O

InChI

InChIKey=UQCNKQCJZOAFTQ-ISWURRPUSA-N
InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H19NO4
Molecular Weight 301.3371
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Oxymorphone is an analgesic that is FDA approved for the treatment of moderate to severe pain. It is also indicated for relief of anxiety in patients with dyspnea associated with pulmonary edema secondary to acute left ventricular dysfunction. Oxymorphone (brand names Opana, Numorphan, Numorphone) is a full opioid agonist and is relatively selective for the mu-opioid receptor, although it can bind to other opioid receptors at higher doses. Adverse reactions (≥ 2% of patients): seen with the immediate release tablet formulation Nausea, pyrexia, somnolence, vomiting, pruritus, headache, dizziness, constipation, and confusion. Concomitant use with serotonergic drugs may result in serotonin syndrome. Avoid use of mixed agonist/antagonist and partial agonist opioid analgesics with Opana because they may reduce analgesic effect of Opana or precipitate withdrawal symptoms.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.93 nM [Ki]
80.5 nM [Ki]
61.6 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
OPANA
Palliative
OPANA

Cmax

ValueDoseCo-administeredAnalytePopulation
0.27 ng/mL
5 mg single, oral
OXYMORPHONE plasma
Homo sapiens
1.21 ng/mL
20 mg single, oral
OXYMORPHONE plasma
Homo sapiens
2.59 ng/mL
40 mg single, oral
OXYMORPHONE plasma
Homo sapiens
0.7 ng/mL
5 mg 2 times / day multiple, oral
OXYMORPHONE plasma
Homo sapiens
2.54 ng/mL
20 mg 2 times / day multiple, oral
OXYMORPHONE plasma
Homo sapiens
4.47 ng/mL
40 mg 2 times / day multiple, oral
OXYMORPHONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4.54 ng × h/mL
5 mg single, oral
OXYMORPHONE plasma
Homo sapiens
17.81 ng × h/mL
20 mg single, oral
OXYMORPHONE plasma
Homo sapiens
37.9 ng × h/mL
40 mg single, oral
OXYMORPHONE plasma
Homo sapiens
5.6 ng × h/mL
5 mg 2 times / day multiple, oral
OXYMORPHONE plasma
Homo sapiens
19.28 ng × h/mL
20 mg 2 times / day multiple, oral
OXYMORPHONE plasma
Homo sapiens
36.98 ng × h/mL
40 mg 2 times / day multiple, oral
OXYMORPHONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.3 h
5 mg single, oral
OXYMORPHONE plasma
Homo sapiens
9.89 h
20 mg single, oral
OXYMORPHONE plasma
Homo sapiens
9.35 h
40 mg single, oral
OXYMORPHONE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Subcutaneous or Intramuscular administration: Initiate treatment with 1mg to 1.5 mg, every 4 to 6 hours. Intravenous Administration: 0.5 mg initially Oral: 10 to 20 mg every four to six hours.
Route of Administration: Other
In Vitro Use Guide
Oxymorphone hydrochloride was not mutagenic when tested in the in vitro bacterial reverse mutation assay (Ames test) at concentrations of ≤5270 ug/plate, or in an in vitro mammalian cell chromosome aberration assay performed with human peripheral blood lymphocytes at concentrations ≤5000 ug/mL with or without metabolic activation.
Substance Class Chemical
Record UNII
9VXA968E0C
Record Status Validated (UNII)
Record Version