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PubMed1978

Simultaneous determination of hydromorphone, hydrocodone and their 6alpha- and 6beta-hydroxy metabolites in urine using selected ion recording with methane chemical ionization.

A selected ion recording using chemical ionization (methane) is described for the simultaneous measurement of hydrocodone, hydromorphone and their respective 6alpha- and 6beta-hydroxymetabolites in human urine. The samples were acid-hydrolyzed, extracted and derivatized by silylation. Only partial resolution of the components on 3% OV-17 was achieved but was sufficient for their determination. The [M+1]+ ions of the drugs and metabolites as well as the [M+29]+ ion of the internal standard were recorded. The assay was sensitive down to c. 0.01 microgram ml-1. The relative standard deviation of standards processed along with the samples ranged from 4.5-8.2%. Hydrocodone was found to be metabolized in man primarily by O-demethylation and 6-keto reduction. Hydromorphone was excreted mainly in the unchanged form (after acid-hydrolysis) with only minor amounts of the 6-hydroxymetabolites being detected. A lack of stereoselectivity in the metabolic reduction ofhydrocodone was observed.

Codeine↗
PubMed1980

Radioimmunoassay of hydromorphone and hydrocodone in human plasma.

A radioimmunoassay for hydromorphone in human plasma was developed using a commercially available morphine-6-antiserum and tritiated dihydromorphine. In the assay, free and bound drug are separated using dextran-coated charcoal. The method quantitates hydromorphone in the 2.5-20-ng/ml range with minimum sensitivity at 1.0 ng/ml. Within-run precision for hydromorphone as shown by the standard error of the estimate of the linear regression equation is +/- 1.01 ng/ml. Between-run precision data for hydromorphone at the 2,5-, 10-, and 20-ng/ml levels gave percent relative standard deviations of 22.35, 10.96, and 8.55%, respectively. A plasma concentration-time curve from a subject administered a single oral dose of hydromorphone demonstrates the usefulness of the assay in monitoring drug levels in a bioavailability study. The method also is applicable to the analysis of hydrocodone in human plasma in the 10-80-ng/ml range with minimum sensitivity at 3.0 ng/ml. Within-run precision for hydrocodone as shown by the standard error of the estimate of the linear regression equation is +/- 1.06 ng/ml. Between-run precision data at the 15-, 30, and 60-ng/ml levels gave percent relative standard deviations of 12.48, 7.67, and 6.03%, respectively.

Codeine↗
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↗
PubMed2002

Combination hydrocodone and ibuprofen versus combination oxycodone and acetaminophen in the treatment of moderate or severe acute low back pain.

BACKGROUND: Introduced in 1997, the combination of hydrocodone and ibuprofen is the only fixed-dose combination analgesic containing an opioid and ibuprofen that has been approved by the US Food and Drug Administration. OBJECTIVE: This study compared the efficacy and tolerability of combination hydrocodone 7.5 mg and ibuprofen 200 mg (HC/IB) with those of combination oxycodone 5 mg and acetaminophen 325 mg (OX/AC) in the treatment of moderate or severe acute low back pain. METHODS: This was a multicenter, randomized, double-blind, parallel-group, repeat-dose study lasting up to 8 days. The recommended dosing of the study medications was 1 tablet every 4 to 6 hours, not to exceed 5 tablets per day. If adequate pain relief was not obtained, patients were permitted to take up to 4 doses per day of supplemental analgesic medication-the nonopioid component of the assigned study medication (ibuprofen 200 mg or acetaminophen 325 mg). Measures of efficacy included mean daily pain relief scores (0 = no relief, 1 = slight relief, 2 = moderate relief, 3 = good relief, and 4 = complete relief), mean daily number of tablets and doses of study medication, mean daily number of tablets and doses of supplemental analgesic medication, global evaluation (poor, fair, good, very good, or excellent), and results on the modified 36-item Short-Form Health Survey (SF-36). All efficacy measures were analyzed on an intent-to-treat basis. Tolerability was evaluated based on adverse events reported spontaneously or elicited by the in vestigators using nonsuggestive questioning, as well as on the number of patients discontinuing treatment because of adverse events. RESULTS: The study enrolled 147 patients (75 HC/IB, 72 OX/AC). The most common cause of low back pain was muscular/ligamentous injury (97/147; 66.0%), followed by degenerative disk disease (27/147; 18.4%). At baseline, 80 patients (54.4%) reported experiencing moderate pain, and 67 patients (45.6%) reported experiencing severe pain. There were no significant differences between HC/IB and OX/AC with regard to mean ( +/- SD) daily pain relief scores (2.40 +/- 1.06 vs 2.50 +/- 1.01, respectively), mean daily number of tablets of study medication (1.80 +/- 1.70 vs 2.20 +/- 1.60), mean daily number of doses of study medication (1.80 +/- 1.65 vs 2.10 +/- 1.58), mean daily number of tablets of supplemental analgesic medication (0.60 +/- 1.13 vs 0.50 +/- 0.99), mean daily number of doses of supplemental analgesic medication (0.60 +/- 1.07 vs 0.50 +/- 0.90), global evaluations, or mean scores on the modified SF-36. In addition, there were no significant differences in the proportion of patients experiencing adverse events with HC/IB (47; 62.7%) and OX/AC (45; 62.5%). Adverse events were consistent with those generally associated with the component analgesics and predominantly involved the central nervous system and gastrointestinal system. CONCLUSIONS: The results of this study suggest that HC/IB and OX/AC are similarly effective and tolerable in relieving moderate or severe acute low back pain. Additional controlled longitudinal trials are necessary to evaluate the clinical utility of HC/IB in treating acute low back pain.

Acetaminophen↗
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↗
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

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

A method is described for the simultaneous analysis of seven opiates, codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone, in blood samples by gas chromatography-mass spectrometry (GC-MS). One milliliter of blood is combined with an internal standard mixture containing 200 ng of each of the seven deuterated opiates. Two milliliters of acetonitrile is added to precipitate the proteins and cellular material. After centrifugation, the clear supernatant is removed, and the acetonitrile is evaporated. The remaining aqueous portion is adjusted to pH 9 with sodium bicarbonate buffer, and the drugs are extracted into chloroform/ trifluoroethanol (10:1). The organic extractant is transferred and dried under nitrogen. The residue is reconstituted in dilute hydrochloric acid and washed consecutively with hexane and chloroform. The purified aqueous portion is adjusted to pH 9 with bicarbonate buffer, and the drugs are again extracted into chloroform/trifluoroethanol (10:1). The organic portion is removed from the aqueous fraction and dried under nitrogen. The residue is consecutively derivatized with methoxyamine and propionic anhydride using pyridine as a catalyst. The ketone groups on hydrocodone, hydromorphone, oxycodone, and oxymorphone are converted to methoximes. Hydroxyl groups present at the O(3) and O(6) positions of codeine, morphine, 6-acetylmorphine, hydromorphone, and oxymorphone are converted to their respective propionyl esters. After a post-derivatization purification step, the extracts are analyzed by full scan GC-MS using electron impact ionization. The method is linear to at least 2000 ng/mL. Day-to-day precision (N = 15) at 500 ng/mL and 75 ng/mL were less than 10% for all seven targeted opiates. Extraction efficiencies at these two concentrations ranged from 50% to 68%. For each opiate, the limit of quantitation was 10 ng/mL, and the limit of detection was 2 ng/mL.

Analgesics, Opioid↗
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↗
PubMed2004

Efficacy of ibuprofen-hydrocodone for the treatment of postoperative pain after periodontal surgery.

BACKGROUND: Previous studies have shown that non-steroidal anti-inflammatory drugs (NSAIDs) have significant benefits in the control of postoperative pain after periodontal or oral surgical procedures. The combination of a peripherally acting NSAID with a centrally acting opioid drug is found to be more effective. The purpose of this study was to compare an alternative combination of ibuprofen 400 mg with 5 mg of hydroxycodone to ibuprofen 400 mg used alone in the management of pain following periodontal surgery. METHODS: This study used a double-masked cross-over design with the patients acting as their own controls. Twelve patients underwent two periodontal surgeries in different quadrants of the same dental arch at least 2 weeks apart. A standardized amount of local anesthetic and similar extent and duration of surgery for each side was required. The patients received four doses of medication at predetermined intervals and filled out a visual analog pain scale every 2 hours for the first 12 hours after surgery. RESULTS: The overall pain reported by the patients on visual analog scale was 1.55 (SE +/- 0.16), out of a possible 10. More pain was reported with ibuprofen alone, 1.81 (SE +/- 0.12), compared to the ibuprofen with hydrocodone combination, 1.30 (SE +/- 0.16). The difference was statistically significant (P<0.05). CONCLUSION: The findings suggest that a combination analgesic preparation of ibuprofen (400 mg) with hydrocodone (5 mg) results in better pain control compared to ibuprofen used alone.

Adult↗
PubMed1997

A pilot study comparing ketoprofen and acetaminophen with hydrocodone for the relief of postoperative periodontal discomfort.

The aim of this study was to compare ketoprofen to acetaminophen with hydrocodone (A/H) in a postoperative periodontal pain model. A double-blind protocol was used. Thirty minutes prior to each procedure, subjects were given orally either 100 mg ketoprofen or a placebo tablet. Four hours later, the subjects took either 50 mg ketoprofen (ketoprofen group) or 1000 mg acetaminophen with 10 mg hydrocodone (placebo group). Subjects reported levels of overall discomfort and pain using visual analog scales at eight hourly intervals following the first dose of ketoprofen or placebo. Information about adverse side effects was requested from the patients in the form of a checklist. The results revealed only small differences between the two drug regimens with respect to levels of pain or overall discomfort. A/H provided significantly better pain relief at Hours 5 and 6, while overall discomfort levels were significantly higher with ketoprofen than with placebo at Hours 3 and 4. Pain levels were low for both groups. It is recommended that additional analgesics for mild to moderate pain should be tested.

Acetaminophen↗
PubMed1999

Inhibitors of cytochrome P450 differentially modify discriminative-stimulus and antinociceptive effects of hydrocodone and hydromorphone in rhesus monkeys.

The present study was conducted to investigate the role of cytochrome P450 in the discriminative-stimulus and antinociceptive effects of hydrocodone (HC) and hydromorphone (HM) in rhesus monkeys. In morphine-deprived monkeys, morphine dose-dependently reversed naltrexone-lever responding, an effect also produced by HC and HM. HC and HM also produced antinociception in a warm-water tail withdrawal procedure. Budipine and naltrexone shifted the dose-effect curves for the discriminative-stimulus effects of HC and HM to the right. In contrast, naltrexone, but not budipine (10.0 mg/kg) or quinidine (10.0 mg/kg), dose-dependently antagonized the antinociceptive effects of HC. Budipine and quinidine decreased the concentration of HM in plasma without significantly affecting the levels of HC, suggesting that these CYP2D6 inhibitors decreased the conversion of HC HM. Thus, some behavioral effects of HC are not modified by a marked inhibition of CYP2D6, suggesting that these effects of HC are not due to its conversion to HM but, rather, that both HC and HM act directly on mu receptors.

Analgesics, Opioid↗
PubMed2002

Synthesis and biological activity of 8beta-substituted hydrocodone indole and hydromorphone indole derivatives.

The 8beta-unsubstituted and substituted analogues of hydrocodone indole and hydromorphone indole were synthesized and their binding affinities to opioid receptors were determined. Introduction of an 8beta-methyl group into the indolomorphinan nucleus increased affinity at all opioid receptors. 6,7-Dehydro-4,5alpha-epoxy-8beta-methyl-6,7,2',3'-indolomorphinan (9) was found to be a delta antagonist with subnanomolar affinity (0.7 nM) for the delta-opioid receptor, and to have good delta-selectivity (mu/delta=322).

Hydrocodone↗
PubMed2002

Simultaneous determination of hydrocodone and hydromorphone in human plasma by liquid chromatography with tandem mass spectrometric detection.

A rapid, sensitive and specific liquid chromatography-tandem mass spectrometry (LC-MS-MS) method has been developed and validated for the simultaneous analysis of hydrocodone (HYC) and its metabolite hydromorphone (HYM) in human plasma. A robotic liquid handler and a 96-channel liquid handling workstation were used to aliquot samples, to add internal standard (I.S.), and to extract analytes of interest. A 96-well mixed-mode solid-phase cartridge plate was used to extract the analytes and I.S. The chromatographic separation was on a silica column (50 x 3 mm, 5-microm) with a mobile phase consisting of acetonitrile, water and trifluoroacetic acid (TFA) (92:8:0.01, v/v). The run time for each injection was 2.5 min with the retention times of approximately 2.1 and 2.2 min for HYC and HYM, respectively. The tandem mass spectrometric detection was by monitoring singly charged precursor-->product ion transition 300-->199 (m/z) for HYC, and 28-->185 (m/z) for HYM. The validated calibration curve range was 0.100-100 ng/ml, based on a plasma volume of 0.3 ml. The correlation coefficients were greater than or equal to 0.9996 for both HYC and HYM. The low limit of quantitation (LLOQ) was 0.100 ng/ml for both HYC and HYM with signal-to-noise ratio (S/N) of 50 and 10. respectively. The deuterated analytes, used as internal standards, were monitored at mass transitions 303-->199 (m/z) for HYC-d3 and 289-->185 (m/z) for HYM-d3. The inter-day (n= 17) precision of the quality control (QC) samples were < or = 3.5% RSD (relative standard deviation) for HYC and < or = 4.7% RSD for HYM, respectively. The inter-day accuracy of the QC samples were < or = 2.1% RE (relative error) for HYC and < or = 1.8% RE for HYM. The intra-day (n=6) precision and accuracy of the QC samples were < or = 2.6% RSD and < or = 3.0% RE for HYC, and < or = 4.7% RSD and < or = 2.4% RE for HYM. There was no significant deviation from the nominal values after a 5-fold dilution of high concentration QC samples by blank matrix. The QC samples were stable when kept at room temperature for 24-h or experienced three freeze-thaw cycles. The extraction recoveries were 86% for HYC and 78% for HYM. No detectable carryover was observed when a blank sample was injected immediately after a 2500 ng/ml sample that was 25-fold more concentrated than the upper limit of quantitation (ULOQ).

Automation↗
PubMedDate not supplied

Hydromorphone and hydrocodone interference in GC/MS assays for morphine and codeine.

The specificity of a GC/MS assay of morphine and codeine was examined with particular regard to the potential interference due to hydromorphone and hydrocodone, compounds that cross-react extensively in opiate screening tests. A GC/MS method with solid-phase extraction and acetylation or trimethylsilylation was used. The equilibrium between keto and enol forms of the potential interferents was evaluated. Sodium borohydride was tried as a means for converting potential interferents into products that are more clearly separated from morphine and codeine. It was found that borohydride reduction proceeded easily and led to products that could be distinguished from morphine and codeine. Moreover, the quantitation of morphine in the presence of hydromorphone was improved if the borohydride step was included in the analysis.

Acetylation↗
PubMed2002

The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid.

Recently, the abuse of prescription opiates as alternatives to heroin has become a national concern. The determination of a six-drug opiate panel, codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, and oxycodone, in hair and oral fluid using solid-phase extraction and capillary gas chromatography-mass spectrometry (GC-MS) is described. Oral fluid was obtained from the donor by insertion of absorptive collectors into the mouth. Hair was collected from the patient and powdered using stainless steel ball bearings in a mini bead-beater apparatus. Opiates present in the samples were extracted from a buffered, aqueous matrix using a solid-phase cartridge. The extracts were concentrated and the methoxime/BSTFA derivatives prepared in order to eliminate interference from the keto-opiates. The extracts were separated by GC-MS in electron impact mode. By utilizing methoxyamine, we were able to produce the methoxime derivatives required for single derivative production and chromatographically separate all six opiates. The routine analysis of these opiates in hair and oral fluid using GC-MS is described for the first time.

Codeine↗
PubMed1987

Death associated with inadvertent hydrocodone overdose in a child with a respiratory tract infection.

A 3-year-old child died of the combined effects of a bacterial superinfection and a relative overdose of hydrocodone prescribed for a cough due to a presumed viral respiratory tract infection. This case illustrates the importance of evaluating the effects of prescribed medication in assessing the cause and mechanism of death in children dying suddenly of presumed natural disease.

Bronchitis↗
PubMedDate not supplied

Hiccup and apparent myoclonus after hydrocodone: review of the opiate-related hiccup and myoclonus literature.

The author recently encountered a patient with hiccups, intermittently accompanied by apparent focal rhythmic diaphragmatic myoclonus after hydrocodone administration. Review of the literature disclosed a paucity of previous reports of hiccup, but many reports of myoclonus after opiate administration. A wide variety of opiates and routes of administration have been implicated, but high doses and the presence of other agents (antipsychotics, antiemetics, nonsteroidal antiinflammatory agents, antidepressants) may pose special risks. Review of the literature suggests three types of opiate-related myoclonus. Opiate-induced myoclonus (OIM) is often generalized and is either periodic or associated with rigidity. Opiate-induced myoclonus frequently occurs in the context of underlying medical conditions, D2 antagonist coadministration, or other drugs (nonsteroidal anti-inflammatory agents, antidepressants), and usually responds to either naloxone or benzodiazepines. Intrathecal OIM has not been linked to D2 antagonist coadministration or benzodiazepine responsiveness but may be associated with non-steroidal antiinflammatory agents. Opiate withdrawal myoclonus may be stimulus-sensitive, associated with D2 antagonist coadministration, and responsive to benzodiazepines and unresponsive to naloxone. There are several problems in interpreting the literature, and more study is needed. Opiatergic, serotonergic, dopaminergic, and other mechanisms are considered.

Analgesics, Opioid↗
PubMed2000

[Evaluation of methods of trace analysis of various opiates including hydrocodone and hydromorphone in the blood and urine using gas chromatography-mass spectrometry].

A GC-MS method suitable to conduct practical trace toxicological analyses of various opiates including hydrocodone or hydromorphone is presented both in scan and selected ion monitoring modes. Silylation can be a convenient reaction to derivatize unknown analytes in toxicological samples. However, silylation of drugs with tautomeric keto/enol groups in molecular structure can cause analytical problems due to poor reproducibility of conversion degree. After using N-Methyl-N-trimethyl-silyltrifluoracetamide (MSTFA) acceptable results were achieved.

Gas Chromatography-Mass Spectrometry↗