OXYCODONE PHOSPHATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21NO4.H3O4P
Molecular Weight	413.3588
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=TZKVACZYAHJHRA-RKXJKUSZSA-N

InChI=1S/C18H21NO4.H3O4P/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;1-5(2,3)4/h3-4,13,16,21H,5-9H2,1-2H3;(H3,1,2,3,4)/t13-,16+,17+,18-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	H3O4P
Molecular Weight	97.9952
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 2678	500.0 nM [EC50]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23880538	Agonist 2678	16000.0 nM [EC50]
Delta opioid receptor 77 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23880538	Agonist 2678	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 8429	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
Opioid-related disorders 6 Sources: https://clinicaltrials.gov/ct2/show/NCT00158184	Primary	Phase II 1132	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
Osteoarthritis 157 Sources: https://clinicaltrials.gov/ct2/show/NCT00985621	Primary	Phase III 656	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

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 1737		substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 97	CYP3A5 395 P-gp 1537 UGT2B7 389 UGT2B4 249	P-gp 257 BCRP 75

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 773	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2802418/	yes
P-gp 1650	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3401600/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27692933/	major
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27692933/	minor
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15039299/	yes
P-gp 1537	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3401600/	yes
CYP2D6 1217	substrate 3367 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 1737	substrate 3367 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
Nav1.5 100	inhibitor 1626 Sources: https://europepmc.org/article/med/29722437
hERG 1647	inhibitor 1626 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
Advancement of opioid analgesia with controlled-release oxycodone.	2001	11798230
Opioid formulations: tailoring to the needs in chronic pain.	2001	11798229
Results of a phase-I/II randomized, masked, placebo-controlled trial of recombinant human interleukin-11 (rhIL-11) in the treatment of subjects with active rheumatoid arthritis.	2001	11438043
Equianalgesic dose ratios for opioids. a critical review and proposals for long-term dosing.	2001 Aug	11495714
"No, Duke. No divorce".	2001 Aug 20	11550441
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
OxyContin abuse.	2001 Feb	11441585
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
Relative variability in bioavailability of oral controlled-release formulations of oxycodone and morphine.	2001 Jul-Aug	11441321
I.v. ketoprofen for analgesia after tonsillectomy: comparison of pre- and post-operative administration.	2001 Mar	11573528
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
Clinical case study.	2001 Nov-Dec	11712728
Acetaminophen, aspirin, or Ibuprofen in combination analgesic products.	2001 Nov-Dec	11704782
Opioid therapy for chronic painful conditions.	2001 Oct	11693049
States respond to growing abuse of painkiller.	2001 Oct-Nov	11763873
Interscalene brachial plexus block with continuous intraarticular infusion of ropivacaine.	2001 Sep	11524326
Oxycodone and oxycontin.	2001 Sep 17	11581580
The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid.	2002 Apr	11991534
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
Severe chronic renal failure in association with oxycodone addiction: a new form of fibrillary glomerulopathy.	2002 Aug	12203209
Minimal interaction between gatifloxacin and oxycodone.	2002 Aug	12162476
Nasal administration of opioids for pain management in adults.	2002 Aug	12139528
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
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	11866386
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
Perioperative management in children with sickle cell disease undergoing laparoscopic surgery.	2002 Jan-Mar	12002293
Gateways to clinical trials.	2002 Jul-Aug	12224444
An evaluation of the efficacy and tolerability of oral tramadol hydrochloride tablets for the treatment of postsurgical pain in children.	2002 Jun	12032009
Comparison of the opioid-sparing efficacy of diclofenac and ketoprofen for 3 days after knee arthroplasty.	2002 Mar	11939925
Validity and reliability of three commercially available breath-by-breath respiratory systems.	2002 Mar	11882930
From physician to inmate.	2002 May	12063835
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
Sevoflurane versus halothane: effect of oxycodone premedication on emergence behaviour in children.	2002 May	11982836
Venous malformations associated with central pain: report of a case.	2002 Nov	12401626
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
Interscalene brachial plexus block is superior to subacromial bursa block after arthroscopic shoulder surgery.	2002 Sep	12190808
Review: tricyclic antidepressants, capsaicin, gabapentin, and oxycodone are effective for postherpetic neuralgia.	2002 Sep-Oct	12207430

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 `Sat Dec 16 18:21:16 GMT 2023` Edited by `admin` on `Sat Dec 16 18:21:16 GMT 2023`
Record UNII	GRM3MU4DWP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYCODONE PHOSPHATE

Common Name

English

MORPHINAN-6-ONE, 4,5-EPOXY-14-HYDROXY-3-METHOXY-17-METHYL-, (5.ALPHA.)-, PHOSPHATE (1:1)

Systematic 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;PHOSPHORIC ACID

Systematic Name

English

OXYCODONE PHOSPHATE SALT

Common Name

English

Code System Code Type Description

CAS

1211844-14-2

Created by admin on Sat Dec 16 18:21:16 GMT 2023 , Edited by admin on Sat Dec 16 18:21:16 GMT 2023

PRIMARY

SMS_ID

300000041678

Created by admin on Sat Dec 16 18:21:16 GMT 2023 , Edited by admin on Sat Dec 16 18:21:16 GMT 2023

PRIMARY

PUBCHEM

68824785

Created by admin on Sat Dec 16 18:21:16 GMT 2023 , Edited by admin on Sat Dec 16 18:21:16 GMT 2023

PRIMARY

FDA UNII

GRM3MU4DWP

Created by admin on Sat Dec 16 18:21:16 GMT 2023 , Edited by admin on Sat Dec 16 18:21:16 GMT 2023

PRIMARY

Related Record Type Details


					CD35PMG570

OXYCODONE

PARENT -> SALT/SOLVATE

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

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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Patents

Sample Use Guides

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T_1/2

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Drug as perpetrator