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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21NO4
Molecular Weight 315.3636
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYCODONE

SMILES

[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5(O)CCC2=O)=CC=C3OC

InChI

InChIKey=BRUQQQPBMZOVGD-XFKAJCMBSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H21NO4
Molecular Weight 315.3636
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://reference.medscape.com/drug/oxycontin-xtampza-er-oxycodone-343321 | https://www.ncbi.nlm.nih.gov/pubmed/23880538 | https://www.drugs.com/oxycodone.html

Oxycodone is a semisynthetic opioid used for the management of acute and chronic pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Oxycodone is a highly selective full agonist of the μ-opioid receptor (MOR), with low affinity for the δ-opioid receptor (DOR) and κ-opioid receptor (KOR). After oxycodone binds to the MOR, a G protein-complex is released, which inhibits the release of neurotransmitters by the cell by reducing the amount of cAMP produced, closing calcium channels, and opening potassium channels. After a dose of conventional (instant-release) oral oxycodone, the onset of action is 10–30 minutes, and peak plasma levels of the drug are attained within roughly 30–60 minutes in contrast, after a dose of OxyContin (an oral controlled-release formulation), peak plasma levels of oxycodone occur in about three hours. The duration of instant-release oxycodone is 3 to 6 hours, although this can be variable depending on the individual. Oxycodone in the blood is distributed to skeletal muscle, liver, intestinal tract, lungs, spleen, and brain. Serious side effects of oxycodone include reduced sensitivity to pain (beyond the pain the drug is taken to reduce), euphoria, anxiolysis, feelings of relaxation, and respiratory depression. Common side effects of oxycodone include constipation (23%), nausea (23%), vomiting (12%), somnolence (23%), dizziness (13%), itching (13%), dry mouth (6%), and sweating (5%).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
500.0 nM [EC50]
16000.0 nM [EC50]
4000.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PERCODAN-DEMI

Approved Use

OxyContin Tablets are a controlled-release oral formulation of oxycodone hydrochloride indicated for the management of moderate to severe pain when a continuous, around-the-clock analgesic is needed for an extended period of time. OxyContin is NOT intended for use as a prn analgesic. Physicians should individualize treatment in every case, initiating therapy at the appropriate point along a progression from non-opioid analgesics, such as non-steroidal anti-inflammatory drugs and acetaminophen to opioids in a plan of pain management such as outlined by the World Health Organization, the Agency for Healthcare Research and Quality (formerly known as the Agency for HealthCare Policy and Research), the Federation of State Medical Boards Model Guidelines, or the American Pain Society. OxyContin is not indicated for pain in the immediate postoperative period (the first 12-24 hours following surgery), or if the pain is mild, or not expected to persist for an extended period of time. OxyContin is only indicated for postoperative use if the patient is already receiving the drug prior to surgery or if the postoperative pain is expected to be moderate to severe and persist for an extended period of time. Physicians should individualize treatment, moving from parenteral to oral analgesics as appropriate. (See American Pain Society guidelines.)

Launch Date

1950
Primary
PERCODAN-DEMI

Approved Use

OxyContin Tablets are a controlled-release oral formulation of oxycodone hydrochloride indicated for the management of moderate to severe pain when a continuous, around-the-clock analgesic is needed for an extended period of time. OxyContin is NOT intended for use as a prn analgesic. Physicians should individualize treatment in every case, initiating therapy at the appropriate point along a progression from non-opioid analgesics, such as non-steroidal anti-inflammatory drugs and acetaminophen to opioids in a plan of pain management such as outlined by the World Health Organization, the Agency for Healthcare Research and Quality (formerly known as the Agency for HealthCare Policy and Research), the Federation of State Medical Boards Model Guidelines, or the American Pain Society. OxyContin is not indicated for pain in the immediate postoperative period (the first 12-24 hours following surgery), or if the pain is mild, or not expected to persist for an extended period of time. OxyContin is only indicated for postoperative use if the patient is already receiving the drug prior to surgery or if the postoperative pain is expected to be moderate to severe and persist for an extended period of time. Physicians should individualize treatment, moving from parenteral to oral analgesics as appropriate. (See American Pain Society guidelines.)

Launch Date

1950
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
19 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
22.2 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
17.7 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
39.3 ng/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
15.7 ng/mL
5 mg 4 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
12.9 ng/mL
3.33 mg 6 times / day steady-state, oral
dose: 3.33 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
105 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
128.2 ng × h/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
133 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
268.2 ng × h/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
113.3 ng × h/mL
5 mg 4 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
99 ng × h/mL
3.33 mg 6 times / day steady-state, oral
dose: 3.33 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.9 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
3.55 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.3 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
3.85 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
55%
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
55%
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
55%
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
55%
5 mg 4 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
55%
3.33 mg 6 times / day steady-state, oral
dose: 3.33 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
OXYCODONE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day single, oral
Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: single
Dose: 30 mg, 1 times / day
Co-administed with::
acetaminophen(1950 mg; single)
cocaine(1/4 g; single)
Sources:
healthy, 30 years
n = 1
Health Status: healthy
Age Group: 30 years
Sex: M
Population Size: 1
Sources:
Other AEs: Pulmonary edema...
Other AEs:
Pulmonary edema
Sources:
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 120
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 120
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Disc. AE: Nausea, Dizziness...
AEs leading to
discontinuation/dose reduction:
Nausea (grade 1-2, 1.7%)
Dizziness (grade 1-2, 1.7%)
Abdominal pain (grade 1-2, 0.8%)
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 125
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 125
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (grade 1-2, 0.8%)
Vomiting (grade 1-2, 0.8%)
Nausea (grade 1-2, 0.8%)
Somnolence (grade 1-2, 0.8%)
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 63
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 63
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Disc. AE: Nausea, Dizziness...
AEs leading to
discontinuation/dose reduction:
Nausea (grade 1-2, 6.3%)
Dizziness (grade 1-2, 4.8%)
Confusion (grade 1-2, 3.2%)
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 126
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 126
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Disc. AE: Vomiting, Flu syndrome...
AEs leading to
discontinuation/dose reduction:
Vomiting (grade 1-2, 0.8%)
Flu syndrome (grade 1-2, 0.8%)
Confusion (grade 1-2, 0.8%)
Fatigue (grade 1-2, 0.8%)
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
6 mg 2 times / day single, oral (mean)
Studied dose
Dose: 6 mg, 2 times / day
Route: oral
Route: single
Dose: 6 mg, 2 times / day
Sources:
healthy, mean age 33 years
n = 35
Health Status: healthy
Age Group: mean age 33 years
Sex: M+F
Population Size: 35
Sources:
Disc. AE: Vomiting...
15 mg 1 times / day single, oral
Studied dose
Dose: 15 mg, 1 times / day
Route: oral
Route: single
Dose: 15 mg, 1 times / day
Sources: Page: nda/2011/202080Orig1s000MedR.pdf - p.22
healthy, mean age 36 years
n = 40
Health Status: healthy
Age Group: mean age 36 years
Sex: M+F
Population Size: 40
Sources: Page: nda/2011/202080Orig1s000MedR.pdf - p.22
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (2.5%)
Sources: Page: nda/2011/202080Orig1s000MedR.pdf - p.22
AEs

AEs

AESignificanceDosePopulation
Pulmonary edema
30 mg 1 times / day single, oral
Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: single
Dose: 30 mg, 1 times / day
Co-administed with::
acetaminophen(1950 mg; single)
cocaine(1/4 g; single)
Sources:
healthy, 30 years
n = 1
Health Status: healthy
Age Group: 30 years
Sex: M
Population Size: 1
Sources:
Abdominal pain grade 1-2, 0.8%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 120
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 120
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Dizziness grade 1-2, 1.7%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 120
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 120
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Nausea grade 1-2, 1.7%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 120
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 120
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Headache grade 1-2, 0.8%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 125
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 125
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Nausea grade 1-2, 0.8%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 125
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 125
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Somnolence grade 1-2, 0.8%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 125
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 125
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Vomiting grade 1-2, 0.8%
Disc. AE
20 mg 2 times / day multiple, oral (mean)
Recommended
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 125
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 125
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Confusion grade 1-2, 3.2%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 63
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 63
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Dizziness grade 1-2, 4.8%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 63
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 63
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Nausea grade 1-2, 6.3%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 63
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 63
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Confusion grade 1-2, 0.8%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 126
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 126
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Fatigue grade 1-2, 0.8%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 126
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 126
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Flu syndrome grade 1-2, 0.8%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 126
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 126
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Vomiting grade 1-2, 0.8%
Disc. AE
5 mg 4 times / day multiple, oral
Recommended
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
unhealthy, adult
n = 126
Health Status: unhealthy
Condition: chronic pain
Age Group: adult
Sex: M+F
Population Size: 126
Sources: Page: /nda/98/20932_medr_P2.pdf - p.21
Vomiting 11.4%
Disc. AE
6 mg 2 times / day single, oral (mean)
Studied dose
Dose: 6 mg, 2 times / day
Route: oral
Route: single
Dose: 6 mg, 2 times / day
Sources:
healthy, mean age 33 years
n = 35
Health Status: healthy
Age Group: mean age 33 years
Sex: M+F
Population Size: 35
Sources:
Vomiting 2.5%
Disc. AE
15 mg 1 times / day single, oral
Studied dose
Dose: 15 mg, 1 times / day
Route: oral
Route: single
Dose: 15 mg, 1 times / day
Sources: Page: nda/2011/202080Orig1s000MedR.pdf - p.22
healthy, mean age 36 years
n = 40
Health Status: healthy
Age Group: mean age 36 years
Sex: M+F
Population Size: 40
Sources: Page: nda/2011/202080Orig1s000MedR.pdf - p.22
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
yes
yes
yes
yes (co-administration study)
Comment: When both oxidative pathways of the metabolism of oxycodone were inhibited with paroxetine and itraconazole (CYP3A4 AND CYP2D6 inhibitors), the mean AUC(0,∞) of oxycodone increased by 2.9-fold (P < 0.001), and its Cmax by 1.8-fold (P < 0.001).
Page: 7.0
yes
yes (co-administration study)
Comment: When both oxidative pathways of the metabolism of oxycodone were inhibited with paroxetine and itraconazole (CYP3A4 AND CYP2D6 inhibitors), the mean AUC(0,∞) of oxycodone increased by 2.9-fold (P < 0.001), and its Cmax by 1.8-fold (P < 0.001).
Tox targets
PubMed

PubMed

TitleDatePubMed
A randomized trial of controlled-release oxycodone during inpatient rehabilitation following unilateral total knee arthroplasty.
2001 Apr
Single-blind randomized clinical trial of laparoscopic versus open appendicectomy in children.
2001 Apr
The preemptive analgesic effect of intraarticular bupivacaine and morphine after ambulatory arthroscopic knee surgery.
2001 Apr
How one town got hooked.
2001 Apr 9
"No, Duke. No divorce".
2001 Aug 20
A curse and a cure. Is the crackdown on an abused drug causing needless suffering?
2001 Aug 6
Identification of ozone-oxidation products of oxycodone by electrospray ion trap mass spectrometry.
2001 Jul
Federal reports say oxycodone abuse is on the rise.
2001 Jul 1
Profits vs. pain relief.
2001 Jul 2
'Not an appropriate use'. Did the makers of OxyContin push too hard?
2001 Jul 2
A retrospective study of the effect of postoperative indomethacin rectal suppositories on the need for narcotic analgesia in patients who had a cesarean delivery while they were under regional anesthesia.
2001 Jun
Prescription for addiction?
2001 Mar
Double-blind, randomized comparison of the analgesic and pharmacokinetic profiles of controlled- and immediate-release oral oxycodone in cancer pain patients.
2001 May
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats.
2001 May
Painkiller crackdown.
2001 May 14
Conversion ratio and cost of oxycodone.
2001 May-Jun
Clinical case study.
2001 Nov-Dec
Acetaminophen, aspirin, or Ibuprofen in combination analgesic products.
2001 Nov-Dec
Opioid therapy for chronic painful conditions.
2001 Oct
States respond to growing abuse of painkiller.
2001 Oct-Nov
Hydromorphone for acute and chronic pain.
2002
The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid.
2002 Apr
Capillary electrophoresis and capillary electrophoresis-ion trap multiple-stage mass spectrometry for the differentiation and identification of oxycodone and its major metabolites in human urine.
2002 Apr 25
A rapid and sensitive high-performance liquid chromatography-electrospray ionization-triple quadrupole mass spectrometry method for the quantitation of oxycodone in human plasma.
2002 Jan
Recovery after tonsillectomy in adults: a three-week follow-up study.
2002 Jan
A comparison of oral transmucosal fentanyl citrate and oral oxycodone for pediatric outpatient wound care.
2002 Jan-Feb
OxyContin and neonatal abstinence syndrome.
2002 Jun
An evaluation of the efficacy and tolerability of oral tramadol hydrochloride tablets for the treatment of postsurgical pain in children.
2002 Jun
Validity and reliability of three commercially available breath-by-breath respiratory systems.
2002 Mar
Pain management after major orthopaedic surgery: current strategies and new concepts.
2002 Mar-Apr
From physician to inmate.
2002 May
Preoperative administration of controlled-release oxycodone for the management of pain after ambulatory laparoscopic tubal ligation surgery.
2002 May
Oral ondansetron, tropisetron or metoclopramide to prevent postoperative nausea and vomiting: a comparison in high-risk patients undergoing thyroid or parathyroid surgery.
2002 May
Sevoflurane versus halothane: effect of oxycodone premedication on emergence behaviour in children.
2002 May
Venous malformations associated with central pain: report of a case.
2002 Nov
Synergy between mu opioid ligands: evidence for functional interactions among mu opioid receptor subtypes.
2002 Nov
Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization.
2002 Oct
Detection of cocaine analytes and opiates in nails from postmortem cases.
2002 Oct
Oxycontin: the concept of a "ghost pill" and the postmortem tissue distribution of oxycodone in 36 cases.
2002 Oct
Pharmacogenomics as molecular autopsy for postmortem forensic toxicology: genotyping cytochrome P450 2D6 for oxycodone cases.
2002 Oct
Determination of 6-oxo-morphinans, as the oximes, by difference circular dichroism spectroscopy.
2002 Oct
Propacetamol as adjunctive treatment for postoperative pain after cardiac surgery.
2002 Oct
Massive OxyContin ingestion refractory to naloxone therapy.
2002 Oct
[Pain therapy in rheumatic diseases. Oxycodon is not a weak opioid].
2002 Sep 12
Paravertebral somatic nerve block compared with peripheral nerve blocks for outpatient inguinal herniorrhaphy.
2002 Sep-Oct
Patents

Sample Use Guides

For opioid naïve patients, initiate treatment with 5 mg to 15 mg every 4 to 6 hours as needed for pain.
Route of Administration: Oral
Human embryonic kidney (HEK)-293 were used for activity evaluation. Receptor G protein-mediated responses were determined by measuring changes in cAMP using the cAMP–homogenous timeresolved fluorescence kit (Cisbio, Codolet, France). MOR, KOR, DOR all couple to Gai so G protein coupling was measured as inhibition of forskolin-stimulated cAMP accumulation in the presence of 1.5 mkM NKH-477 (water-soluble forskolin, Tocris catalog #1603) and 500 mkM 3-isobutyl-1-methylxanthine (IBMX). cAMP accumulation assays were run in parallel with b-arrestin-2 recruitment, using the same cells, drug dilutions, and assay buffers [1% dimethylsulfoxide (DMSO), F12 Ham’s buffer] to ensure accurate assay-to-assay comparisons of data. Plates were read using a time-resolved fluorescence ratio (665 nm/620 nm) on a PheraStar plate reader
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:07 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:07 GMT 2023
Record UNII
CD35PMG570
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYCODONE
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
OXYCODONE [HSDB]
Common Name English
IDS-NO-002
Code English
oxycodone [INN]
Common Name English
14-HYDROXYDIHYDROCODEINONE
Common Name English
OXYCODONE [MI]
Common Name English
OXYCODONE [VANDF]
Common Name English
OXYCODONE [MART.]
Common Name English
OXYCODONE [ORANGE BOOK]
Common Name English
Oxycodone [WHO-DD]
Common Name English
OXYCODONE [USAN]
Common Name English
OXYCODONE CII
USP-RS  
Common Name English
4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Systematic Name English
(5.ALPHA.)-4,5-EPOXY-14-HYDROXY-3-METHOXY-17-METHYLMORPHINAN-6-ONE
Systematic Name English
NSC-19043
Code English
XTAMPZA ER
Brand Name English
REMOXY
Brand Name English
PTI-821
Code English
PAVINAL
Common Name English
N02AA05
Code English
XTAMPZA
Common Name English
(-)-14-HYDROXYDIHYDROCODEINONE
Common Name English
OXYMORPHONE 3-METHYL ETHER
Common Name English
OXYCODONE CII [USP-RS]
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY D [EP IMPURITY]
Common Name English
MORPHINAN-6-ONE, 4,5-EPOXY-14-HYDROXY-3-METHOXY-17-METHYL-, (5.ALPHA.)-
Systematic Name English
PF-00345439
Code English
DIHYDRONE
Common Name English
PTI 821
Common Name English
Classification Tree Code System Code
WHO-ATC N02AA56
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-ATC N02AA05
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-VATC QN02AA05
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
LIVERTOX NBK547955
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
DEA NO. 9143
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
NDF-RT N0000175690
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-ATC N02AJ18
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-VATC QN02AA55
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-ATC N02AJ19
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
NDF-RT N0000175684
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-ATC N02AJ17
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
WHO-ATC N02AA55
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5023407
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
IUPHAR
7093
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
PUBCHEM
5284603
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
SMS_ID
100000083302
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
ChEMBL
CHEMBL656
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
FDA UNII
CD35PMG570
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-960-2
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
DAILYMED
CD35PMG570
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
HSDB
3142
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
RS_ITEM_NUM
1485191
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
MESH
D010098
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
CAS
76-42-6
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
MERCK INDEX
m8328
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
OXYCODONE
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
DRUG BANK
DB00497
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
NSC
19043
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
LACTMED
Oxycodone
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
NCI_THESAURUS
C29309
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
CHEBI
7852
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
EVMPD
SUB09562MIG
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
RXCUI
7804
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2029
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
INN
1701
Created by admin on Fri Dec 15 15:03:07 GMT 2023 , Edited by admin on Fri Dec 15 15:03:07 GMT 2023
PRIMARY
Related Record Type Details
DERIVATIVE -> PARENT
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
LABELED -> NON-LABELED
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
TARGET -> AGONIST
Related Record Type Details
METABOLITE -> PARENT
MAJOR
PLASMA; URINE
METABOLITE ACTIVE -> PARENT
MINOR
PLASMA; URINE
METABOLITE ACTIVE -> PARENT
Highly variable 40 fold higher potency than Oxycodone
MINOR
PLASMA; URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC