Oxycodone

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

SMILES

COC1=CC=C2C[C@H]3N(C)CC[C@@]45[C@@H](OC1=C24)C(=O)CC[C@@]35O

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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 229	Agonist 2,741	500.0 nM [EC50]
Kappa opioid receptor 113	Agonist 2,741	16000.0 nM [EC50]
Delta opioid receptor 80	Agonist 2,741	4000.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Acute and chronic pain 6	Primary	Approved 8,548	PERCODAN-DEMI
Opioid-related disorders 6	Primary	Phase II 1,145	PERCODAN-DEMI
Osteoarthritis 157	Primary	Phase III 664	PERCODAN-DEMI

C_max

Value	Dose	Analyte	Population
22.2 ng/mL	15 mg single, oral	OXYCODONE plasma	Homo sapiens
39.3 ng/mL	30 mg single, oral	OXYCODONE plasma	Homo sapiens
19 ng/mL	10 mg single, oral	OXYCODONE plasma	Homo sapiens
17.7 ng/mL	10 mg single, oral	OXYCODONE plasma	Homo sapiens
15.7 ng/mL	5 mg 4 times / day steady-state, oral	OXYCODONE plasma	Homo sapiens
12.9 ng/mL	3.33 mg 6 times / day steady-state, oral	OXYCODONE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
128.2 ng × h/mL	15 mg single, oral	OXYCODONE plasma	Homo sapiens
268.2 ng × h/mL	30 mg single, oral	OXYCODONE plasma	Homo sapiens
105 ng × h/mL	10 mg single, oral	OXYCODONE plasma	Homo sapiens
133 ng × h/mL	10 mg single, oral	OXYCODONE plasma	Homo sapiens
113.3 ng × h/mL	5 mg 4 times / day steady-state, oral	OXYCODONE plasma	Homo sapiens
99 ng × h/mL	3.33 mg 6 times / day steady-state, oral	OXYCODONE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.55 h	15 mg single, oral	OXYCODONE plasma	Homo sapiens
3.85 h	30 mg single, oral	OXYCODONE plasma	Homo sapiens
2.9 h	10 mg single, oral	OXYCODONE plasma	Homo sapiens
3.3 h	10 mg single, oral	OXYCODONE plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
55%	15 mg single, oral	OXYCODONE plasma	Homo sapiens
55%	30 mg single, oral	OXYCODONE plasma	Homo sapiens
55%	10 mg single, oral	OXYCODONE plasma	Homo sapiens
55%	10 mg single, oral	OXYCODONE plasma	Homo sapiens
55%	5 mg 4 times / day steady-state, oral	OXYCODONE plasma	Homo sapiens
55%	3.33 mg 6 times / day steady-state, oral	OXYCODONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
30 mg 1 times / day single, oral Studied dose	healthy, 30 years	Other AEs: Pulmonary edema...
20 mg 2 times / day multiple, oral Recommended	unhealthy, adult	Disc. AE: Nausea, Dizziness...
20 mg 2 times / day multiple, oral Recommended	unhealthy, adult	Disc. AE: Headache, Vomiting...
5 mg 4 times / day multiple, oral Recommended	unhealthy, adult	Disc. AE: Nausea, Dizziness...
5 mg 4 times / day multiple, oral Recommended	unhealthy, adult	Disc. AE: Vomiting, Flu syndrome...

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AEs

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AE	Significance	Dose	Population
Pulmonary edema		30 mg 1 times / day single, oral Studied dose	healthy, 30 years
Abdominal pain	grade 1-2, 0.8% Disc. AE	20 mg 2 times / day multiple, oral Recommended	unhealthy, adult
Dizziness	grade 1-2, 1.7% Disc. AE	20 mg 2 times / day multiple, oral Recommended	unhealthy, adult
Nausea	grade 1-2, 1.7% Disc. AE	20 mg 2 times / day multiple, oral Recommended	unhealthy, adult
Headache	grade 1-2, 0.8% Disc. AE	20 mg 2 times / day multiple, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,929		substrate 1,378	inhibitor 2,195

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 115	CYP3A5 443 P-gp 2,035 UGT2B7 455 UGT2B4 277	P-gp 296 BCRP 101

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 974	inducer 1,947	yes
P-gp 1,915	inducer 1,947	yes

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Drug as victim

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Target	Modality	Activity	Clinical evidence
UGT2B7 455	substrate 3,987	major
UGT2B4 277	substrate 3,987	minor
CYP3A5 443	substrate 3,987	yes
P-gp 2,035	substrate 3,987	yes
CYP2D6 1,378	substrate 3,987	yes	yes (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 118	inhibitor 2,215
hERG 2,240	inhibitor 2,215

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
A randomized trial of controlled-release oxycodone during inpatient rehabilitation following unilateral total knee arthroplasty.	2001 Apr	11315787
Equianalgesic dose ratios for opioids. a critical review and proposals for long-term dosing.	2001 Aug	11495714
Federal reports say oxycodone abuse is on the rise.	2001 Jul 1	11449872
Stability indicating HPLC method for the estimation of oxycodone and lidocaine in rectal gel.	2001 Jul 31	11451631
[Treatment of pain in cancer with systemically administered opioids].	2001 May 19	11396259

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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
Record UNII	CD35PMG570
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

Oxycodone

Official Name

English

N02AA05

Preferred Name

English

OXYCODONE [HSDB]

Common Name

English

IDS-NO-002

Code

English

oxycodone [INN]

Common Name

English

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Classification Tree

Code System

Code

Natural opium alkaloids

WHO-ATC

N02AA56

Natural opium alkaloids

WHO-ATC

N02AA05

Natural opium alkaloids

WHO-VATC

QN02AA05

Agent Affecting Nervous System

NCI_THESAURUS

C67413

Moderate pain

LIVERTOX

NBK547955

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Code System

Code

Type

Description

EPA CompTox

DTXSID5023407

PRIMARY

IUPHAR

7093

PRIMARY

PUBCHEM

5284603

PRIMARY

SMS_ID

100000083302

PRIMARY

ChEMBL

CHEMBL656

PRIMARY

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Related Record

Type

Details


					1BI24NT4VF

8.BETA.-HYDROXYOXYCODONE

DERIVATIVE -> PARENT

Amount:


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET -> AGONIST

Amount:


					M04XWV43UF

OXYCODONE TEREPHTHALATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:

RELATIONSHIP_AMOUNT 79 (average)


					GRM3MU4DWP

OXYCODONE PHOSPHATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:

RELATIONSHIP_AMOUNT 76 (average)


					4P6424D07T

OXYCODONE HYDROCHLORIDE TRIHYDRATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:

RELATIONSHIP_AMOUNT 78 (average)

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Related Record

Type

Details


					95Q949779D

NOROXYCODONE

METABOLITE -> PARENT

Interaction Type:

MAJOR

Qualification:

PLASMA; URINE

Amount:


					9NZ7111A9O

Noroxymorphone

METABOLITE ACTIVE -> PARENT

Interaction Type:

MINOR

Qualification:

PLASMA; URINE

Amount:


					9VXA968E0C

OXYMORPHONE

METABOLITE ACTIVE -> PARENT

Comments:

Highly variable 40 fold higher potency than Oxycodone

Interaction Type:

MINOR

Qualification:

PLASMA; URINE

Amount:

RELATIONSHIP_AMOUNT 10 MOLE PERCENT (average)

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Related Record

Type

Details


					NO70W886KK

HYDROCODONE BITARTRATE

PARENT -> IMPURITY

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Related Record

Type

Details


					CD35PMG570

Oxycodone

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount
Volume of Distribution	PHARMACOKINETIC	2.6 Liters/Kilogram (average)
MAXIMUM TOLERATED DOSE	TOXICITY	288 mg/day (average) ORAL DOSE
Tmax	PHARMACOKINETIC	4.5 hours (average) ORAL DOSE

Biological Half-life	PHARMACOKINETIC	[3 to 5] hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator