OXYCODONE MYRISTATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21NO4.C14H28O2
Molecular Weight	543.7346
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OIORLIPHCJBIJB-RKXJKUSZSA-N

InChI=1S/C18H21NO4.C14H28O2/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;1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h3-4,13,16,21H,5-9H2,1-2H3;2-13H2,1H3,(H,15,16)/t13-,16+,17+,18-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C14H28O2
Molecular Weight	228.3709
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/202080s005s006lbl.pdf
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%).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23880538	Agonist 2637	500.0 nM [EC50]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23880538	Agonist 2637	16000.0 nM [EC50]
Delta opioid receptor 78 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23880538	Agonist 2637	4000.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute and chronic pain 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/202080s005s006lbl.pdf	Primary	Approved 8307	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 -6.224256E11
Opioid-related disorders 6 Sources: https://clinicaltrials.gov/ct2/show/NCT00158184	Primary	Phase II 1133	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 -6.224256E11
Osteoarthritis 155 Sources: https://clinicaltrials.gov/ct2/show/NCT00985621	Primary	Phase III 651	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 -6.224256E11

C_max

Value	Dose	Analyte	Population
19 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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

Value	Dose	Analyte	Population
105 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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

T_1/2

Value	Dose	Analyte	Population
2.9 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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

F_unbound

Value	Dose	Analyte	Population
55% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021011s002lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/1994955/	healthy, 30 years n = 1 Health Status: healthy Age Group: 30 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1994955/	Other AEs: Pulmonary edema... Other AEs: Pulmonary edema Sources: https://pubmed.ncbi.nlm.nih.gov/1994955/
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf https://pubmed.ncbi.nlm.nih.gov/22717418/	healthy, mean age 33 years n = 35 Health Status: healthy Age Group: mean age 33 years Sex: M+F Population Size: 35 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf https://pubmed.ncbi.nlm.nih.gov/22717418/	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (11.4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf https://pubmed.ncbi.nlm.nih.gov/22717418/
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf Page: nda/2011/202080Orig1s000MedR.pdf - p.22	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (2.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf Page: nda/2011/202080Orig1s000MedR.pdf - p.22

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1670		substrate 1168	inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 95	CYP3A5 383 P-gp 1491 UGT2B7 387 UGT2B4 248	P-gp 252 BCRP 74

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 751	inducer 1515 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2802418/	yes
P-gp 1588	inducer 1515 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3401600/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT2B7 387	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/27692933/	major
UGT2B4 248	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/27692933/	minor
CYP3A5 383	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15039299/	yes
P-gp 1491	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3401600/	yes
CYP2D6 1168	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21011lbl.pdf#page=7; https://pubmed.ncbi.nlm.nih.gov/21142269/ 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). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21011lbl.pdf#page=7; https://pubmed.ncbi.nlm.nih.gov/21142269/ Page: 7.0
CYP3A4 1670	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15039299/; https://pubmed.ncbi.nlm.nih.gov/21142269/	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). Sources: https://pubmed.ncbi.nlm.nih.gov/15039299/; https://pubmed.ncbi.nlm.nih.gov/21142269/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 98	inhibitor 1584 Sources: https://europepmc.org/article/med/29722437
hERG 1603	inhibitor 1584 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2670374/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7852	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7852
ZINC	ZINC000000403533	http://zinc15.docking.org/substances/ZINC000000403533

PubMed

Title	Date	PubMed
Opioid formulations: tailoring to the needs in chronic pain.	2001	11798229
Strategies for the treatment of cancer pain in the new millennium.	2001	11434451
Equianalgesic dose ratios for opioids. a critical review and proposals for long-term dosing.	2001 Aug	11495714
Time-release analgesic drug causes fatal overdoses in United States.	2001 Aug	11483541
A curse and a cure. Is the crackdown on an abused drug causing needless suffering?	2001 Aug 6	11499370
Opioid analgesic prescribing and use - an audit of analgesic prescribing by general practitioners and The Multidisciplinary Pain Centre at Royal Brisbane Hospital.	2001 Dec	11736881
Identification of ozone-oxidation products of oxycodone by electrospray ion trap mass spectrometry.	2001 Jul	11473402
Federal reports say oxycodone abuse is on the rise.	2001 Jul 1	11449872
Profits vs. pain relief.	2001 Jul 2	11447813
'Not an appropriate use'. Did the makers of OxyContin push too hard?	2001 Jul 2	11447650
Stability indicating HPLC method for the estimation of oxycodone and lidocaine in rectal gel.	2001 Jul 31	11451631
Prescription for addiction?	2001 Mar	12400320
Drug dependence studies and regulations: an overview of the past and present.	2001 Nov	11797422
The use of oxycodone in cancer-related pain: a literature review.	2001 Nov	11775926
Controlled-release oxycodone hydrochloride (OxyContin).	2001 Sep	11855610
Interscalene brachial plexus block with continuous intraarticular infusion of ropivacaine.	2001 Sep	11524326
Valdecoxib.	2002	12269850
Oxy's offspring.	2002 Apr 22	11974393
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	12013227
More blame and praise for a pain drug.	2002 Apr 29	11989324
Minimal interaction between gatifloxacin and oxycodone.	2002 Aug	12162476
Treatment of postherpetic neuralgia: a systematic review of the literature.	2002 Feb	11978209
Comparison of pre- and postoperative administration of ketoprofen for analgesia after tonsillectomy in children.	2002 Feb	11882229
Comparison of the pharmacokinetics of oxycodone administered in three Percocet formulations.	2002 Feb	11831542
Treatment of painful sickle cell leg ulcers with topical opioids.	2002 Feb 1	11822360
The influence of anaesthesia and surgery on the circadian rhythm of melatonin.	2002 Jan	11903069
Combination hydrocodone and ibuprofen versus combination oxycodone and acetaminophen in the treatment of moderate or severe acute low back pain.	2002 Jan	11833838
Recovery after tonsillectomy in adults: a three-week follow-up study.	2002 Jan	11802045
A comparison of oral transmucosal fentanyl citrate and oral oxycodone for pediatric outpatient wound care.	2002 Jan-Feb	11803309
Safety and efficacy of controlled-release oxycodone: a systematic literature review.	2002 Jul	12126222
Gateways to clinical trials.	2002 Jul-Aug	12224444
OxyContin and neonatal abstinence syndrome.	2002 Jun	12032797
An evaluation of the efficacy and tolerability of oral tramadol hydrochloride tablets for the treatment of postsurgical pain in children.	2002 Jun	12032009
There is no accounting for accountability.	2002 Mar	11884858
Validity and reliability of three commercially available breath-by-breath respiratory systems.	2002 Mar	11882930
OxyContin Use and Abuse.	2002 Mar-Apr	11889673
The analgesic efficacy of valdecoxib vs. oxycodone/acetaminophen after oral surgery.	2002 May	12036167
Preoperative administration of controlled-release oxycodone for the management of pain after ambulatory laparoscopic tubal ligation surgery.	2002 May	12031758
Oral ondansetron, tropisetron or metoclopramide to prevent postoperative nausea and vomiting: a comparison in high-risk patients undergoing thyroid or parathyroid surgery.	2002 May	12027845
Venous malformations associated with central pain: report of a case.	2002 Nov	12401626
Synergy between mu opioid ligands: evidence for functional interactions among mu opioid receptor subtypes.	2002 Nov	12388636
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	12423011
Detection of cocaine analytes and opiates in nails from postmortem cases.	2002 Oct	12423005
Oxycontin: the concept of a "ghost pill" and the postmortem tissue distribution of oxycodone in 36 cases.	2002 Oct	12422999
Pharmacogenomics as molecular autopsy for postmortem forensic toxicology: genotyping cytochrome P450 2D6 for oxycodone cases.	2002 Oct	12422998
Determination of 6-oxo-morphinans, as the oximes, by difference circular dichroism spectroscopy.	2002 Oct	12373390
Propacetamol as adjunctive treatment for postoperative pain after cardiac surgery.	2002 Oct	12351250
Massive OxyContin ingestion refractory to naloxone therapy.	2002 Oct	12239500
[Pain therapy in rheumatic diseases. Oxycodon is not a weak opioid].	2002 Sep 12	12380334
Paravertebral somatic nerve block compared with peripheral nerve blocks for outpatient inguinal herniorrhaphy.	2002 Sep-Oct	12373694

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Sun Dec 18 21:33:50 UTC 2022` Edited by `admin` on `Sun Dec 18 21:33:50 UTC 2022`
Record UNII	96P3HS657Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYCODONE MYRISTATE

Common Name

English

(4R,4AS,7AR,12BS)-4A-HYDROXY-9-METHOXY-3-METHYL-2,4,5,6,7A,13-HEXAHYDRO-1H-4,12-METHANOBENZOFURO(3,2-E)ISOQUINOLIN-7-ONE TETRADECANOATE

Systematic Name

English

FORMED FROM OXYCODONE IN DETERX ER

Brand Name

English

Code System Code Type Description

FDA UNII

96P3HS657Y

Created by admin on Sun Dec 18 21:33:50 UTC 2022 , Edited by admin on Sun Dec 18 21:33:50 UTC 2022

PRIMARY

PUBCHEM

118947059

Created by admin on Sun Dec 18 21:33:50 UTC 2022 , Edited by admin on Sun Dec 18 21:33:50 UTC 2022

PRIMARY

Related Record Type Details


					CD35PMG570

OXYCODONE

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					CD35PMG570

OXYCODONE

ACTIVE MOIETY

Amount:

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/1994955/	healthy, 30 years n = 1 Health Status: healthy Age Group: 30 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1994955/
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20932_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf https://pubmed.ncbi.nlm.nih.gov/22717418/	healthy, mean age 33 years n = 35 Health Status: healthy Age Group: mean age 33 years Sex: M+F Population Size: 35 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf https://pubmed.ncbi.nlm.nih.gov/22717418/
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/202080Orig1s000MedR.pdf Page: nda/2011/202080Orig1s000MedR.pdf - p.22

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Approved Use

Launch Date

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Funbound

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Overview

OverviewOther

Drug as perpetrator​

Drug as victim

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PubMed

Patents

Sample Use Guides

C_max

T_1/2

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Drug as perpetrator