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PubMed2004

Identification of new oxycodone metabolites in human urine by capillary electrophoresis-multiple-stage ion-trap mass spectrometry.

Capillary electrophoresis-electrospray ionization multiple-stage ion-trap mass spectrometry (CE-MSn) and computer simulation of fragmentation are demonstrated to be effective tools to detect and identify phase I and phase II metabolites of oxycodone (OCOD) in human urine. OCOD is a strong analgesic used for the management of moderate to severe mainly postoperative or cancer-related pain whose metabolism in man is largely unknown. Using an aqueous pH 9 ammonium acetate buffer and CE-MSn (n < or = 5), OCOD and its phase I metabolites produced by O-demethylation, N-demethylation, 6-ketoreduction and N-oxidation (such as oxymorphone, noroxycodone, noroxymorphone, 6-oxycodol, nor-6-oxycodol, oxycodone-N-oxide and 6-oxycodol-N-oxide) and phase II conjugates with glucuronic acid of several of these compounds could be detected in alkaline solid-phase extracts of a patient urine that was collected during a pharmacotherapy episode with daily ingestion of 240-320 mg of OCOD chloride. The data for three known OCOD metabolites for which the standards had to be synthesized in-house, 6-oxycodol, nor-6-oxycodol and oxycodone-N-oxide, were employed to identify two new metabolites, the N-oxidized derivative of 6-oxycodol and an O-glucuronide of this compound. CE-MSn and computer simulation of fragmentation also led to the identification of the N-glucuronide of noroxymorphone, another novel OCOD metabolite for which no standard compound or mass spectra library data were available.

Analgesics, Opioid↗

PubMed1998

Codeine and oxycodone use in patients with chronic rheumatic disease pain.

OBJECTIVE: Opioid treatment of chronic rheumatic disease pain is controversial because of concerns regarding efficacy, toxicity, tolerance, dependence, and abuse. This study examined opioid use in a cohort of patients with pain due to defined rheumatic diseases. METHODS: Opioid use was studied retrospectively in a cohort of 644 rheumatology clinic patients. Computerized pharmacy records identified patients who had been prescribed opioids during the previous 3 years. Medical records were reviewed to determine reasons for opioid dosage escalations. Patients were interviewed to determine efficacy, frequency and types of side effects, and history of alcohol or street-drug abuse. RESULTS: Opioid prescriptions were found in the 3-year pharmacy database for 290 of 644 clinic patients: 153 for <3 consecutive months and 137 for > or =3 months. All opioid-treated patients received codeine and/or oxycodone. In this cohort, 133 patients in each opioid-treated group and 76 of the 354 non-opioid-treated control patients were studied. Opioids significantly reduced rheumatic disease pain severity scores from 8.2 to 3.6 (on a 0-10 scale) (P < 0.001). Mild side effects were reported in 38%; nausea, dyspepsia, constipation, and sedation were the most common. The mean +/-SD initial dosage was 2.1+/-1.7 30-mg codeine equivalents/day, the mean peak was 3.4+/-3.3 per day, and the mean current dose was 2.7+/-2.0 per day. Dosage escalations occurred in 32 patients and were attributable to worsening of the underlying painful condition or a medical complication thereof in all but 4 patients, who also displayed other abuse behaviors. Abuse behaviors were not more frequent in those with or without a history of abuse/ addiction. CONCLUSION: Prolonged treatment of rheumatic disease pain with codeine or oxycodone was effective in reducing pain severity and was associated with only mild toxicity. Doses were stable for prolonged periods of time, with escalations of the opioid dose almost always related to worsening of the painful condition or a complication thereof, rather than the development of tolerance to opioids. Doubts or concerns about opioid efficacy, toxicity, tolerance, and abuse or addiction should no longer be used to justify withholding opioids from patients with well-defined rheumatic disease pain.

Aged↗

PubMed1979

Determination of oxycodone in plasma and identification of a major metabolite.

An electron-capture GLC method is described for oxycodone and its major metabolite, noroxycodone, in plasma and urine. The method involves extraction of the two substances into benzene-isopropranol at pH 10.4, followed by back-extraction into 0.1 N HCl. The acid phase is washed with hexane and made alkaline prior to reextraction into benzene-isopropanol. The solvent is removed by evaporation, and the heptafluorobutyryl derivatives of the test substances are formed. After removal of excess reagent, oxycodone and noroxycodone are quantitated by GLC. The characteristics of both substances, with respect to plasma levels in dogs and analgesic activity in mice, are reported. Isolation of noroxycodone from human urine and its identification by TLC, GLC, and mass spectrometry are described.

Analgesics, Opioid↗

PubMed2005

Simultaneous determination of morphine, oxycodone, morphine-3-glucuronide, and noroxycodone concentrations in rat serum by high performance liquid chromatography-electrospray ionization-tandem mass spectrometry.

An assay using high performance liquid chromatography (HPLC)-electrospray ionization-tandem mass spectrometry (ESI-MS-MS) was developed for simultaneously determining concentrations of morphine, oxycodone, morphine-3-glucuronide, and noroxycodone, in 50 microl samples of rat serum. Deuterated (d(3)) analogues of each compound were used as internal standards. Samples were treated with acetonitrile to precipitate plasma proteins; acetonitrile was removed from the supernatant by centrifugal evaporation before analysis. Limits of quantitation (ng/ml) and their between-day accuracy and precision (%deviation and %CV) were--morphine, 3.8 (4.3% and 7.6%); morphine-3-glucuronide, 5.0 (4.5% and 2.9%); oxycodone, 4.5 (0.4% and 9.3%); noroxycodone, 5.0 (8.5% and 4.6%).

Animals↗

PubMed2006

Low-level quantitation of oxycodone and its oxidative metabolites, noroxycodone, and oxymorphone, in rat plasma by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry.

A method was developed for quantification of oxycodone, noroxycodone, and oxymorphone in small volumes (50 microl) of rat plasma by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry using turbo ion-spray. Deuterated (d3) opioid analogues acted as internal standards. Sample preparation involved protein precipitation with acetonitrile, centrifugal evaporation, and reconstitution in mobile phase; analyte separation was performed on a C18 (5 microm, 2.1 mm x 50 mm) column using a linear gradient program. Lower limits of quantitation (ng/ml) and their between-day accuracy and precision were-oxycodone, 0.9 (-0.2 and 7.8%); noroxycodone, 1.0 (0.6 and 6.2%); oxymorphone 1.0 (-1.8 and 9.5%).

Analgesics, Opioid↗

PubMed2006

Determination of meperidine, tramadol and oxycodone in human oral fluid using solid phase extraction and gas chromatography-mass spectrometry.

Analytical procedures for the determination of meperidine, tramadol and oxycodone in oral fluid have been developed and validated using gas chromatography-mass spectrometry (GC/MS) following initial screening with enzyme linked immunosorbent assay (ELISA). The oral fluid samples were collected using the Quantisal device, and any drugs present were quantified using mixed mode solid-phase extraction and electron impact GC/MS. For confirmation, three ions were monitored and two ion ratios determined, which were within 20% of those of the known calibration standards. The limits of quantitation were 10 ng/mL; the intra-day precision of the assays (n=5) was 2.33%, 1.00% and 7.61%; inter-day precision 2.48%, 2.44% and 5.8% (n=10) for meperidine, tramadol and oxycodone, respectively. The percentage recovery of the drugs from the collection pads was 86.7%, 87.7% and 96.6%, respectively (n=6). The methods were applied to specimens obtained during research studies in the USA.

Analgesics↗

PubMed2006

Response to hydrocodone, codeine and oxycodone in a CYP2D6 poor metabolizer.

Codeine is metabolized by the cytochrome P450 2D6 (CYP2D6) to morphine. Codeine is a much weaker agonist at mu opioid receptors than morphine. Therefore, codeine analgesia is highly dependent on CYP2D6 activity. Large prospective studies in the clinical environment do not exist, but it appears reasonable to avoid codeine use in CYP2D6 poor metabolizers (PMs). CYP2D6 metabolizes other opioid analgesics, including tramadol, dihydrocodeine, oxycodone and hydrocodone, although they have been less systematically studied. It is unclear whether these other pro-drugs may be as completely dependent on CYP2D6 for their analgesia as codeine. We describe a patient identified as a CYP2D6 PM with a history of problems with opioid analgesics. The patient was an 85-year-old female Caucasian who had hip surgery. The patient had a long-standing intolerance to codeine. In her first admission, she couldn't tolerate the regimen of oxycodone combined with tramadol prns (as needed). She was genotyped as a CYP2D6 PM and after the information was provided to the treating physician in her second admission, she seemed to have a better response to hydrocodone. Large case-control naturalistic studies followed by randomized trials in patients taking opioid analgesics may be needed to definitively establish that CYP2D6 genotyping has clinical relevance in the use of several opioid analgesics.

Aged, 80 and over↗

PubMed2003

Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection.

High-performance liquid chromatographic assays for the O- and N-demethylated oxidative metabolites of hydrocodone and oxycodone formed in human liver microsomes are described. A solvent-solvent extraction/re-extraction procedure followed by reversed-phase HPLC with UV detection at 210 nm allows for the quantification of hydromorphone, norhydrocodone, oxymorphone and noroxycodone. Calibration curve concentration ranges were 0.63-400 microM (0.18-114 microg/ml) and 1.25-400 microM (0.36-114 microg/ml) for hydromorphone and norhydrocodone, respectively and 0.13-20 microM (0.04-6.03 microg/ml) and 1-200 microM (0.30-60 microg/ml) for oxymorphone and noroxycodone, respectively. Assay performance was determined by intra- and inter-assay precision and inaccuracies for quality control samples and was <15% for all metabolites at each quality control concentration. These methods provide good precision, accuracy and sensitivity for use in in vitro kinetic studies investigating the oxidative metabolism of hydrocodone and oxycodone in human liver microsomes.

Chromatography, High Pressure Liquid↗

PubMed1993

Ketoprofen, acetaminophen plus oxycodone, and acetaminophen in the relief of postoperative pain.

Ketoprofen (Orudis) is a nonsteroidal anti-inflammatory drug that is currently approved in the United States for the management of mild to moderate pain. The objective of this trial was to determine the effectiveness of orally administered ketoprofen in the management of severe postoperative pain. This randomized, double-blind parallel study compared the efficacy and safety of single doses of 100 mg or 50 mg ketoprofen, the combination of 650 mg acetaminophen plus 10 mg oxycodone hydrochloride, 650 mg acetaminophen, or placebo in 240 patients with severe postoperative pain after cesarean section. Analgesia for the first dose was assessed over an 8-hour period. Multiple doses of 100 mg or 50 mg ketoprofen and the combination at half the dose (325 mg acetaminophen plus 5 mg oxycodone) were also assessed for up to 7 days. The 100 and 50 mg doses of ketoprofen and the combination were statistically superior to acetaminophen and placebo for many analgesic measures. A dose response was observed between the two doses of ketoprofen, with the 100 mg dose providing significantly greater analgesia over the lower dose. Ketoprofen, 100 mg, was at least as effective as the combination and its effects lasted longer, with the exception of hour 1 when the combination was superior. Remedication time for the group receiving 100 mg ketoprofen was significantly longer than for the other treatment groups. Significantly more patients who took repeated doses of the combination (84%) than those who took either dose of ketoprofen (70%) had adverse effects. Ketoprofen at both dose levels was shown to be effective, long-lasting, and well tolerated, and it should be considered as a viable option for the management of moderate to severe postoperative pain.

Acetaminophen↗

PubMed2002

Sevoflurane versus halothane: effect of oxycodone premedication on emergence behaviour in children.

BACKGROUND: Clinical studies have provided conflicting conclusions about whether the frequency of emergence agitation is increased in children following sevoflurane anaesthesia. The purpose of the study was to determine a frequency and duration of agitation with halothane and sevoflurane anaesthesia and whether oxycodone premedication affected the incidence of emergence agitation in children. METHODS: We measured and compared halothane and sevoflurane recovery in 130 patients using a 5-point scale measuring emergence behaviour every 10 min during the first 60 min of recovery or until discharge. RESULTS: We used this 5-point scale to assess the presence or absence of emergence agitation and found a frequency of emergence agitation of more than 40% in children who received halothane and sevoflurane anaesthesia. CONCLUSIONS: Oxycodone reduced the frequency of agitation in children who received halothane, but not in the children who received sevoflurane anaesthesia.

Anesthetics, Inhalation↗

PubMed2002

Severe chronic renal failure in association with oxycodone addiction: a new form of fibrillary glomerulopathy.

A number of well-documented renal lesions have been associated with intravenous drug use. Recently, investigators reported three cases of granulomatous glomerulonephritis in association with intravenous injection of oxycodone suppositories. We report 2 patients with similar glomerular pathology who presented with chronic renal failure. However, we also highlight the widespread tubulointerstitial involvement in this renal lesion. The fibrillar deposits seen within the glomeruli and extensively within tubular basement membranes on electron microscopy do not have the staining characteristics of amyloid and are not associated with immunoglobulin (Ig) deposition. Is this a new form of non-Ig-associated fibrillary glomerulopathy with its pathogenesis linked to some component of the oxycodone suppositories? One of the patients had a history of narcotic addiction but denied intravenous injection of suppositories. In both patients there was progressive deterioration of renal function with 1 patient requiring dialysis within 3 months of initial presentation.

Adult↗

PubMed2004

Controlled-release oxycodone is better tolerated than intravenous tramadol/metamizol for postoperative analgesia after retinal-surgery.

PURPOSE: We assessed the clinical efficacy and tolerance of controlled-release oxycodone (CRO), comparing it with intravenous tramadol/metamizol combination in this prospective, randomised, double-blind study of 35 ASA physical status I-III patients undergoing retinal-surgery. METHODS: General anaesthesia using remifentanil and propofol was performed for surgery. On arrival in the recovery room patients were randomly allocated to two groups. The controlled-release oxycodone group (CRO Group) received 10 mg CRO. 12 h after the initial dose another 10 mg CRO were administered. Simultaneously with the initial CRO dose, and every 4 h up to 24 h postoperatively, the CRO Group received intravenous isotonic saline infusion. On arrival in the recovery room the tramadol/metamizol group (TM Group) received a placebo tablet, and 12 h later a second placebo. Simultaneously 100 mg tramadol combined with 1 g metamizol were administered intravenously every 4 h until 24 h postoperatively. All patients had access to intravenous opioid rescue medication. RESULTS: The AUC for quality of analgesia was significantly higher in the CRO Group than in the TM Group (p = 0.0023). Patient rated quality of analgesia significantly higher in the CRO Group than in the TM Group 8 h (p = 0.048), 16 h (p = 0.009) and 24 h (p = 0.001) postoperatively. There was no statistical difference in AUC for pain scores between groups (p = 0.205). The CRO Group experienced significantly less nausea than the TM Group (p = 0.012). Six patients in the TM Group in contrast to none in the CRO Group interrupted the study before finishing the study protocol (p = 0.022). CONCLUSIONS: We conclude that CRO administered twice in the first 24 h postoperatively is superior to intravenous tramadol/metamizol for postoperative analgesia after retinal surgery, with fewer adverse events and greater patient satisfaction.

Adolescent↗

PubMed1980

Comparison of i.m. lysine acetylsalicylate and oxycodone in the treatment of pain after operation.

Lysine acetylsalicylate (LAS) is a soluble salt of acetylsalicylic acid and can be given parenterally. LAS 12.5 mg kg-1 and 25 mg kg-1 were compared with oxycodone 0.15 mg kg-1 in the treatment of pain after operation in 60 patients undergoing varicose vein surgery. Both treatments almost completely relieved moderate to severe pain for the 3-h observation period. The time until the peak of action was longer after LAS (60-90 min) than after oxycodone (30-60 min). No significant differences were found between the smaller and larger doses of LAS, suggesting a plateau effect. Further clinical experiments with LAS using i.v. mode of administration and other pain models are warranted.

Adult↗

PubMed2002

A rapid and sensitive high-performance liquid chromatography-electrospray ionization-triple quadrupole mass spectrometry method for the quantitation of oxycodone in human plasma.

A sensitive method for the determination of oxycodone concentrations in plasma by high-performance liquid chromatography (HPLC)-electrospray ionization-triple quadrupole mass spectrometry is described. The method is rugged, reliable, selective, and rapid with a run time of 2 min. One milliliter of plasma is made basic and extracted with 2-mL duplicate portions of 2% isoamyl alcohol in n-butyl chloride. The combined extracts are then evaporated to dryness, reconstituted in 100 microL of the mobile phase (15% methanol-85% water containing 0.1% acetic acid), and injected onto the HPLC. The limit of quantitation is 1 ng/mL, and the estimated limit of detection is 33 pg/mL (signal-to-noise = 3). Standard curves are linear over the range of 1 to 100 ng/mL with all correlation coefficient values greater than 0.9989. The method is used to determine the concentration of oxycodone in human plasma following the intravenous infusion of doses ranging from 5 to 15 mg in which the analysis of over 3000 plasma samples is required.

Analgesics, Opioid↗

PubMedDate not supplied

GC-MS confirmation of codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone in urine.

A procedure for the simultaneous confirmation of codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone in urine specimens by gas chromatography-mass spectrometry (GC-MS) is described. After the addition of nalorphine and naltrexone as the two internal standards, the urine is hydrolyzed overnight with beta-glucuronidase from E. coli. The urine is adjusted to pH 9 and extracted with 8% trifluoroethanol in methylene dichloride. After evaporating the organic, the residue is sequentially derivatized with 2% methoxyamine in pyridine, then with propionic anhydride. The ketone groups on hydrocodone, hydromorphone, oxycodone, oxymorphone, and naltrexone are converted to their respective methoximes. Available hydroxyl groups on the O3 and O6 positions are converted to propionic esters. After a brief purification step, the extracts are analyzed by GC-MS using full scan electron impact ionization. Nalorphine is used as the internal standard for codeine, morphine, and 6-acetylmorphine; naltrexone is used as the internal standard for the 6-keto-opioids. The method is linear to 2000 ng/mL for the 6-keto-opioids and to 5000 ng/mL for the others. The limit of quantitation is 25 ng/mL in hydrolyzed urine. Day-to-day precision at 300 and 1500 ng/mL ranged between 6 and 10.9%. The coefficients of variation for 6-acetylmorphine were 12% at both 30 and 150 ng/mL. A list of 38 other basic drugs or metabolites detected by this method is tabulated.

Codeine↗

PubMedDate not supplied

Patient characteristics and risks factors for development of dependence on hydrocodone and oxycodone.

The purpose of the study was to document the substantial increase in problematic use of hydrocodone and oxycodone in an addiction treatment population. Our study consisted of a retrospective review of medical records from all patients admitted and discharged in 2000 from Sparrow/St. Lawrence Addiction Detoxification Unit (N = 534). A literature review was conducted in medical journals, governmental groups, and reports including Drug Abuse Warning Network, Pharmacy Times, and National Household Survey on Drug Abuse. More than 144 patients (27%) were dependent on prescription opiate medications. The most frequently mentioned medication was Vicodin (hydrocodone) (53% of the users) followed by OxyContin (oxycodone) (19%). Physicians commonly prescribed these medications (75% of the cases). Predictors of dependence on opiate medications included substance-related diagnoses, positive toxicology for opiates, and other medical diagnoses. Patients under the care of physicians who have other drug dependence diagnoses and medical complaints appear at risk of developing dependence on prescription opiate medications. Proper evaluation and intervention can limit adverse consequences of prescription opiate medications.

Adult↗

PubMedDate not supplied

Impact of controlled-release oxycodone on efficacy beliefs and coping efforts among osteoarthritis patients with moderate to severe pain.

OBJECTIVES: This study examines the impact of controlled-release oxycodone (OxyContin) on cognitive-behavioral indicators of efficacy beliefs and coping efforts in patients with osteoarthritis who experience persistent pain. METHODS: This was a double-blind, placebo-controlled study of 104 male and female patients with osteoarthritis who experienced moderate to severe pain. Pain assessment, arthritis helplessness, and coping efforts were assessed before and after for treatment and placebo control groups. RESULTS: Examination of differences between treatment and control groups after 2 weeks revealed significant reductions in reported pain, improvements in coping efficacy, and reductions in helplessness and passive coping in response to controlled-release oxycodone treatment compared to placebo. Changes in pain partially mediated the effects on coping in subsequent assessments. DISCUSSION: The findings indicate that controlled-release oxyco- done treatment accounted for improvements in coping with pain beyond that of placebo controls. This medication may be most beneficial to osteoarthritis patients when incorporated as part of a multidisciplinary approach to pain management.

Adaptation, Psychological↗

PubMed2004

An unusual fatality in a child due to oxycodone.

An unusual fatality secondary to oxycodone in a child is reported. A 2-year-old female child was conveyed to a local hospital after exhibiting signs of rubbing of the mouth and staggering. A hospital toxicological immunoassay screen for drugs of abuse and tricyclic antidepressants was performed on a urine sample and reported as negative. She was discharged and found unresponsive the next morning. She was conveyed to a second hospital in full cardiopulmonary arrest and despite resuscitative efforts, was pronounced dead upon arrival. An autopsy was performed and postmortem specimens were submitted and screened for drugs using mainly chromatographic techniques. Quantitation was achieved by gas chromatography with nitrogen phosphorus detection. Confirmation was performed by gas chromatography/mass spectrometry. Oxycodone was the only drug detected in the following concentrations: heart blood, 1.36 mg/L; gastric contents, 7.33 mg in 33 mL (222.34 mg/L); liver, 0.2 mg/kg; and urine, 47.23 mg/L (47,230 ng/mL). In addition, immunoassay testing of the urine was positive for the opiate class of drugs. This case report demonstrates an unusual cause of death in a young child with emphasis on potential limitation in hospital urine screening tests and the importance of complete forensic toxicological testing in all child deaths.

Accidents↗