OXYMORPHONE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=UQCNKQCJZOAFTQ-ISWURRPUSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/011707s036lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021611lbl.pdf | https://www.drugs.com/pro/oxymorphone.html

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

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: Sinatra R.S., Jahr J.S., Watkins-Pitchford J.M.. (2010) 'The Essence of Analgesia and Analgesics', p.124 Retrieved from \| https://books.google.ru/books?id=ZwPIjKg0XukC	Agonist 2678	0.93 nM [Ki]
Delta opioid receptor 77 Target ID: CHEMBL236 Sources: Sinatra R.S., Jahr J.S., Watkins-Pitchford J.M.. (2010) 'The Essence of Analgesia and Analgesics', p.124 Retrieved from \| https://books.google.ru/books?id=ZwPIjKg0XukC	Agonist 2678	80.5 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24919067	Agonist 2678	61.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/011707s036lbl.pdf	Palliative		Approved 8429	OPANA Approved Use Enter section text here - OPANA ER is an opioid agonist indicated for the relief of moderate to severe pain in patients requiring continuous around-the-clock opioid treatment for an extended period of time. (1) - Not intended for use as an as needed analgesic. Not indicated in the immediate post-operative period or if the pain is mild or not expected to persist for an extended period of time. (1), 1 INDICATIONS AND USAGE 1 INDICATIONS AND USAGE OPANA ER is indicated for the relief of moderate to severe pain in patients requiring continuous, around-the-clock opioid treatment for an extended period of time. Limitations of Usage OPANA ER is not intended for use as an as needed analgesic. OPANA ER is not indicated for pain in the immediate post-operative period if the pain is mild, or not expected to persist for an extended period of time. OPANA ER is only indicated for post-operative use if the patient is already receiving the drug prior to surgery or if the post-operative pain is expected to be moderate or 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 1959
Anxiety 267 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/011707s036lbl.pdf	Palliative		Approved 8429	OPANA Approved Use Enter section text here - OPANA ER is an opioid agonist indicated for the relief of moderate to severe pain in patients requiring continuous around-the-clock opioid treatment for an extended period of time. (1) - Not intended for use as an as needed analgesic. Not indicated in the immediate post-operative period or if the pain is mild or not expected to persist for an extended period of time. (1), 1 INDICATIONS AND USAGE 1 INDICATIONS AND USAGE OPANA ER is indicated for the relief of moderate to severe pain in patients requiring continuous, around-the-clock opioid treatment for an extended period of time. Limitations of Usage OPANA ER is not intended for use as an as needed analgesic. OPANA ER is not indicated for pain in the immediate post-operative period if the pain is mild, or not expected to persist for an extended period of time. OPANA ER is only indicated for post-operative use if the patient is already receiving the drug prior to surgery or if the post-operative pain is expected to be moderate or 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 1959

C_max

Value	Dose	Analyte	Population
0.27 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.21 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2.59 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.7 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.54 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.47 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	40 mg 2 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
4.54 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
17.81 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
37.9 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5.6 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
19.28 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
36.98 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	40 mg 2 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
11.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.89 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
9.35 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/201655s016lbl.pdf	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYMORPHONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
20 mg 4 times / day multiple, oral Recommended Dose: 20 mg, 4 times / day Route: oral Route: multiple Dose: 20 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15777102	healthy, 27–44 Health Status: healthy Age Group: 27–44 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15777102	Disc. AE: Vomiting, Nausea... AEs leading to discontinuation/dose reduction: Vomiting (mild, 4.3%) Nausea (4.3%) Dizziness (4.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/15777102
79.4 mg 1 times / day multiple, oral Highest studied dose Dose: 79.4 mg, 1 times / day Route: oral Route: multiple Dose: 79.4 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629415	unhealthy, 45.5-47.5 Health Status: unhealthy Age Group: 45.5-47.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15629415	Disc. AE: Abdominal pain, Chest pain... AEs leading to discontinuation/dose reduction: Abdominal pain (1.4%) Chest pain (1.4%) Serum creatine phosphokinase increased (1.4%) Serum creatine phosphokinase MB increased (1.4%) Back pain (1.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/15629415
0.5 mg 5 times / day multiple, intravenous Recommended Dose: 0.5 mg, 5 times / day Route: intravenous Route: multiple Dose: 0.5 mg, 5 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/011707s031lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/011707s031lbl.pdf	Disc. AE: Opioid abuse, Respiratory depression... AEs leading to discontinuation/dose reduction: Opioid abuse Respiratory depression Addiction Hypotension (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/011707s031lbl.pdf
1.5 mg 5 times / day multiple, intramuscular\|subcutaneous Recommended Dose: 1.5 mg, 5 times / day Route: intramuscular\|subcutaneous Route: multiple Dose: 1.5 mg, 5 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/011707s031lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/011707s031lbl.pdf	Disc. AE: Opioid abuse, Respiratory depression... AEs leading to discontinuation/dose reduction: Opioid abuse Respiratory depression Addiction Hypotension (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/011707s031lbl.pdf
20 mg 5 times / day multiple, oral Recommended Dose: 20 mg, 5 times / day Route: oral Route: multiple Dose: 20 mg, 5 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021611s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021611s010lbl.pdf	Disc. AE: Opioid abuse, Addiction... AEs leading to discontinuation/dose reduction: Opioid abuse Addiction Respiratory depression (grade 3-5) Withdrawal syndrome neonatal Anaphylaxis Hypotension (severe) Angioedema Hypersensitivity reaction Adrenal insufficiency Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021611s010lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781	inducer 389

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 450 18	CYP 450 31

Drug as perpetrator

Target	Modality	Activity
CYP 450 20	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201655lbl.pdf#page=19 Page: 19.0	no
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201655lbl.pdf#page=11 Page: 11.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201655lbl.pdf#page=11 Page: 11.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 450 31	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/201655lbl.pdf#page=19 Page: 19.0	no

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	MT-57608	http://www.ahhchemical.com/product/MT-57608.html
Alsachim	4226	http://www.alsachim.com/product-C5544-glo.bal-view.html
Ambinter	Amb22801505	http://www.ambinter.com/reference/22801505
Aurora Fine Chemicals LLC	A17.921.625	http://online.aurorafinechemicals.com/info?ID=A17.921.625
Avantor Inc	75835-940	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
BioCrick	BCC5255	http://www.biocrick.com/Oxymorphone-BCC5255.html
Chem Scene	CS-2852	http://www.chemscene.com/Oxymorphone.html
ChemMol	30105081	http://www.chemmol.com/chemmol/30105081.html
LGC Standards	LGCAMP0673.01-01	https://www.lgcstandards.com/US/en/p/LGCAMP0673.01-01
LGC Standards	LGCAMP0673.01-02	https://www.lgcstandards.com/US/en/p/LGCAMP0673.01-02
MedChem Express	HY-B0618	http://www.medchemexpress.com/Oxymorphone.html
Sigma-Aldrich	O-004_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/o004?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S619016	https://www.smolecule.com/products/s619016

PubMed

Title	Date	PubMed
Investigation of the selectivity of oxymorphone- and naltrexone-derived ligands via site-directed mutagenesis of opioid receptors: exploring the "address" recognition locus.	2001 Mar 15	11300867
Investigation of 4,5-epoxymorphinan degradation during analysis by HPLC.	2002 Aug 22	12151069
Reliability of goniometry in Labrador Retrievers.	2002 Jul	12118679
Synergy between mu opioid ligands: evidence for functional interactions among mu opioid receptor subtypes.	2002 Nov	12388636
Oxymorphone--Endo/Penwest: EN 3202, EN 3203.	2003	12757410
A single dose of liposome-encapsulated oxymorphone or morphine provides long-term analgesia in an animal model of neuropathic pain.	2003 Jun	12868573
Liposome-encapsulated oxymorphone hydrochloride provides prolonged relief of postsurgical visceral pain in rats.	2003 Jun	12868572
Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, part I.	2003 Mar-Apr	12618536
Tentative identification of novel oxycodone metabolites in human urine.	2003 Sep	14516487
The use of liquid chromatography/mass spectrometry for quantitative analysis of oxycodone, oxymorphone and noroxycodone in Ringer solution, rat plasma and rat brain tissue.	2004	15468158
Effects of acepromazine on the incidence of vomiting associated with opioid administration in dogs.	2004 Jan	14756752
The efficacy and safety of oral immediate-release oxymorphone for postsurgical pain.	2004 Nov	15502051
Evaluation of liposome-encapsulated oxymorphone hydrochloride in mice after splenectomy.	2004 Oct	15575370
Gluten exorphin B5 stimulates prolactin secretion through opioid receptors located outside the blood-brain barrier.	2005 Feb 25	15698850
Efficacy and safety of oxymorphone extended release in chronic low back pain: results of a randomized, double-blind, placebo- and active-controlled phase III study.	2005 Jan	15629415
Effectiveness and safety of oral extended-release oxymorphone for the treatment of cancer pain: a pilot study.	2005 Jan	15538638
GC-MS quantitation of codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone in blood.	2005 Jul-Aug	16105253
Oxymorphone extended release does not affect CYP2C9 or CYP3A4 metabolic pathways.	2005 Mar	15703368
Direct analysis of opiates in urine by liquid chromatography-tandem mass spectrometry.	2005 Oct	16419404
Comparison of the pharmacokinetics of oxycodone and noroxycodone in male dark agouti and Sprague--Dawley rats: influence of streptozotocin-induced diabetes.	2005 Sep	16132361
Oxymorphone extended-release tablets relieve moderate to severe pain and improve physical function in osteoarthritis: results of a randomized, double-blind, placebo- and active-controlled phase III trial.	2005 Sep-Oct	16266356
Dissociative anaesthesia during field and hospital conditions for castration of colts.	2006	16722301
Oxymorphone: a review.	2006 Feb	16317569
Controlled clinical trials in cancer pain. How controlled should they be? A qualitative systematic review.	2006 Jun 5	16705312
Opioid receptor-mediated hyperalgesia and antinociceptive tolerance induced by sustained opiate delivery.	2006 Mar 20	16343768
Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites.	2006 May	16678548
Incomplete recovery of prescription opioids in urine using enzymatic hydrolysis of glucuronide metabolites.	2006 Oct	17132254
GC-MS analysis of multiply derivatized opioids in urine.	2007 Aug	17567826
Comment: Oral oxymorphone for pain management.	2007 Dec	17971405
Activation of kappa-opioid receptor as a method for prevention of ischemic and reperfusion arrhythmias: role of protein kinase C and K(ATP) channels.	2007 Feb	17970197
Extended-duration agents for perioperative pain management.	2007 Feb	17214919
Effect of naloxone-3-glucuronide and N-methylnaloxone on the motility of the isolated rat colon after morphine.	2007 Feb	17211696
Evidence that oxymorphone-induced increases in micronuclei occur secondary to hyperthermia.	2007 Feb	17077185
A 12-week, randomized, placebo-controlled trial assessing the safety and efficacy of oxymorphone extended release for opioid-naive patients with chronic low back pain.	2007 Jan	17257473
Oral extended-release oxymorphone: a new choice for chronic pain relief.	2007 Jul	17661733
Use of oral oxymorphone in the elderly.	2007 May	17658959
Sex differences in the pharmacokinetics, oxidative metabolism and oral bioavailability of oxycodone in the Sprague-Dawley rat.	2008 Mar	17973932

Patents

Sample Use Guides

In Vivo Use Guide

Subcutaneous or Intramuscular administration: Initiate treatment with 1mg to 1.5 mg, every 4 to 6 hours. Intravenous Administration: 0.5 mg initially Oral: 10 to 20 mg every four to six hours.

Route of Administration: Other

In Vitro Use Guide

Oxymorphone hydrochloride was not mutagenic when tested in the in vitro bacterial reverse mutation assay (Ames test) at concentrations of ≤5270 ug/plate, or in an in vitro mammalian cell chromosome aberration assay performed with human peripheral blood lymphocytes at concentrations ≤5000 ug/mL with or without metabolic activation.

Name

Type

Language

OXYMORPHONE

Official Name

English

OXYMORPHONE CII [USP-RS]

Common Name

English

OXYCODONE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Common Name

English

4,5.ALPHA.-EPOXY-3,14-DIHYDROXY-17-METHYLMORPHINAN-6-ONE

Systematic Name

English

NIH 10323

Code

English

OXYMORPHONE [VANDF]

Common Name

English

OXYCODONE HYDROCHLORIDE IMPURITY, OXYMORPHONE- [USP IMPURITY]

Common Name

English

DIHYDROXYMORPHINONE

Common Name

English

IDS-NO-003

Code

English

MORPHINAN-6-ONE, 4,5-EPOXY-3,14-DIHYDROXY-17-METHYL-

Systematic Name

English

14-HYDROXYDIHYDROMORPHINONE

Common Name

English

oxymorphone [INN]

Common Name

English

OXYMORPHONE CII

Common Name

English

7,8-DIHYDRO-14-HYDROXYMORPHINONE

Common Name

English

Oxymorphone [WHO-DD]

Common Name

English

OXYMORPHONE [MI]

Common Name

English

NSC-19045

Code

English

Classification Tree Code System Code

NDF-RT

N0000175690