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PubMed2005

Structure investigation of codeine drug using mass spectrometry, thermal analyses and semi-emperical molecular orbital (MO) calculations.

Codeine is an analgesic with uses similar to morphine, but it has a mild sedative effect. It is preferable used as phosphate form and it is often administrated by mouth with aspirin or paracetamol. Therefore, it is important to investigate its structure to know the active groups and weak bonds responsible for its medical activity. Consequently in the present work, codeine was investigated by mass spectrometry and thermal analyses (TG, DTG and DTA) and confirming by semi-empirical MO-calculation (PM3 method) in the neutral and positively charged forms of the drug. Some results of studying the d-block element complexes of codeine were used to declare the relationship between drug structure and its chemical reactivity in vitro system. The mass spectra and thermal analyses fragmentation pathways were proposed and compared to each other to select the most suitable scheme representing the correct fragmentation of this drug. From EI mass spectra, the main primary cleavage site of the charged drug molecule is that due to beta-cleavage to nitrogen atom in its skeleton. It occurs in two parallel mechanisms with the same possibility, i.e. no difference in appearance activation energy between them. In the neutral drug form the primary site cleavage is that occurs in the ether ring. Thermal analyses of the neutral form of the drug revealed the high response of the drug to the temperature variation with very fast rate. It decomposed in several sequential steps in the temperature range 200-600 degrees C. The initial thermal fragments are very similar to that obtained by mass spectrometric fragmentation. Therefore, comparison between mass and thermal helps in selection of the proper pathway representing the fragmentation of this drug. This comparison successfully confirmed by MOC. These calculations give the bond order, charge distribution, heat of formation and possible hybridization of some atoms in different position of the drug skeleton. This helps the successful choice of the weakest bond at which both mass and thermal fragmentation occurs. Therefore, the best fragmentation pathway of this drug is correctly selected. The effect of such fragmentation on the drug behavior in the human body can be expected as a result of comparing these data with that obtained on studying codeine metal complexes using mass and thermal fragmentation techniques.

Carbon Radioisotopes↗

PubMed1997

Differential effect of codeine on coughs caused by mechanical stimulation of two different sites in the airway of guinea pigs.

We studied the difference in the effects of codeine on coughs caused by mechanical stimulation to the larynx and to the bifurcation of the trachea in lightly anaesthetized guinea pigs. Mechanical stimulation to the larynx or the bifurcation of trachea caused a stable cough response. The response was reproducible over 60 min, when stimulation was repeatedly applied at 20-min intervals. No significant difference was found between the amplitudes of the responses to mechanical stimulation of the larynx and of the tracheal bifurcation. Codeine, 10, 20 and 50 mg/kg, dose dependently depressed the coughs caused by larynx stimulation. The antitussive, however, failed to depress the cough caused by stimulation to the tracheal bifurcation, although a large dose, 50 mg/kg, significantly depressed the cough. In capsaicin-treated guinea pigs, codeine at 20 mg/kg significantly depressed the cough caused by stimulation to the tracheal bifurcation. The present results suggest that cough caused by mechanical stimulation to the larynx might be more sensitive to codeine treatment than cough caused by stimulation to the bifurcation of trachea. Furthermore, it is suggested that coughs caused by mechanical stimulation to both sites might consist of at least two components as regards their pharmacological nature.

Animals↗

PubMed2000

Combination hydrocodone and ibuprofen versus combination codeine and acetaminophen for the treatment of chronic pain.

OBJECTIVE: The objective of this study was to compare the effectiveness of combination hydrocodone 7.5 mg and ibuprofen 200 mg with that of combination codeine 30 mg and acetaminophen 300 mg for the treatment of chronic pain. BACKGROUND: Hydrocodone 7.5 mg with ibuprofen 200 mg is the only approved fixed-dose combination analgesic containing an opioid and ibuprofen. METHODS: In this randomized, parallel-group, double-blind, repeated-dose, active-comparator, 4-week, multicenter study, 469 patients were randomly assigned to receive a 1-tablet (n = 156) or 2-tablet (n = 153) dose of combination hydrocodone 7.5 mg and ibuprofen 200 mg (HI1 and HI2, respectively) or a 2-tablet dose of combination codeine 30 mg and acetaminophen 300 mg (CA, n = 160), the active comparator, every 6 to 8 hours as needed for pain. Efficacy was measured through pain relief scores, number of daily doses of study medication, number of daily doses of supplemental analgesics, number of patients who discontinued therapy due to an unsatisfactory analgesic response, and global assessment scores. RESULTS: Of the 469 patients, 255 (54.4%) were female and 214 (45.6%) were male. The mean age was 51.1 years. Types of chronic pain included back (214; 45.6%), arthritic (145; 30.9%), other musculoskeletal (65; 13.9%), cancer (6; 1.3%), diabetic neuropathic (3; 0.6%), postherpetic neuralgic (5; 1.1%), other neurologic (21; 4.5%), and other unclassified chronic pain (10; 2.1%). During the 48 hours prior to the study, 351 (74.8%) patients had been treated with opioid or opioid-nonopioid combination analgesics. The overall mean daily pain relief score was significantly greater in the HI2 group (2.25+/-0.89) than in the HI1 group (1.98+/-0.87) (P = 0.003) or the CA group (1.85+/-0.96) (P < 0.001). The overall mean number of daily doses of study medication was significantly less in the HI2 group (2.94+/-0.99) than in the HI1 group (3.23+/-0.76) (P = 0.036) or the CA group (3.26+/-0.75) (P = 0.014). The overall mean number of daily doses of supplemental analgesics was significantly less in the HI2 group (0.24+/-0.49) than in the HI1 group (0.34+/-0.58) (P = 0.021) or CA group (0.49+/-0.85) (P = 0.010). The number of patients who discontinued treatment due to an unsatisfactory analgesic response was significantly less in the HI2 group (2; 1.3%) than in the CA group (12; 7.5%) (P = 0.008). HI2 was more effective than HI1 and CA as measured by pain relief scores for week 1 (P < 0.001 vs HI1 and CA), week 2 (P < 0.001 vs HI1 and CA), and week 3 (P = 0.008 vs HI1 and P < 0.001 vs CA); daily doses of study medication for week 1 (P = 0.019 vs HI1 and P = 0.011 vs CA); daily doses of supplemental analgesics for week 1 (P = 0.010 vs HI1 and CA); and global assessment scores for week 1 (P = 0.018 vs HI1 and P < 0.001 vs CA), week 2 (P = 0.005 vs HI1 and P < 0.001 vs CA), and week 4 (P = 0.013 vs HI1 and P = 0.023 vs CA). There were no significant differences between HI1 and CA in any efficacy variable. There were no significant differences in the number of patients experiencing adverse events in the HI2 (127; 83%), HI1 (124; 79.5%), and CA (129; 80.6%) groups. However, the mean number of patients who discontinued treatment due to adverse events was significantly greater in the HI2 group (40; 26.1%) than in the HI1 group (23; 14.7%) (P = 0.013). CONCLUSIONS: The results of this study suggest that 2-tablet doses of combination hydrocodone 7.5 mg and ibuprofen 200 mg may be more effective than either 1-tablet doses of this combination or 2-tablet doses of combination codeine 30 mg and acetaminophen 300 mg. Moreover, 1-tablet doses of combination hydrocodone 7.5 mg and ibuprofen 200 mg may be as effective as 2-tablet doses of combination codeine 30 mg and acetaminophen 300 mg.

Acetaminophen↗

PubMed1988

Excessive grooming induced by the administration of codeine and morphine.

Previous studies have shown that peripheral injections of the codeinone RX 336-M can induce excessive grooming in rats in an age-dependent fashion. The present experiment demonstrates that codeine, itself, also induces excessive grooming but with apparent equal effectiveness at all ages tested. Because of the structural similarity between codeine and morphine, the effects of intraperitoneally administered morphine were examined as well. Morphine was found to produce a temporal course of excessive grooming quite different from that produced by codeine. Morphine did not affect grooming in the first half (30 min) of the observation period, but accentuated it, briefly, for the next 30-45 min. Intraventricular administration of codeine at doses of 0.3 or 1.0 microgram/3 microliter had no effect on grooming in animals previously shown to demonstrate excessive grooming in response to either dose.

Aging↗

PubMed1991

Hydrocodone versus codeine in acute musculoskeletal pain.

STUDY OBJECTIVES: To evaluate the efficacy and prevalence of side effects of hydrocodone versus codeine in acute pain syndromes. TYPE OF PARTICIPANTS/SETTING: Sixty-two consecutive adult emergency department patients 18 to 70 years old with acute musculoskeletal pain. Patients using other analgesics or having any contraindication to opioid therapy were excluded. In addition, 12 patients were excluded because of insufficient data or study dropout. DESIGN/INTERVENTIONS: In a randomized, double-blind prospective manner, patients received either 5 mg hydrocodone with 500 mg acetaminophen or 30 mg codeine with 500 mg acetaminophen to take on discharge from the ED and every four hours thereafter as needed for pain. MEASUREMENTS: Pain intensity was evaluated by a visual analog scale at zero, one, two, four, eight, 24, and 48 hours. Specific side effects were sought, along with the number of patients reporting inadequate analgesia. MAIN RESULTS: Data were obtained on 50 subjects (25 per group). Mean and median pain scores did not differ significantly at time zero (x vs y, 6.03 vs 5.99 and 6.8 vs 6.1, respectively) or subsequent intervals. Side effects were noted in eight hydrocodone/acetaminophen and 18 codeine/acetaminophen patients (P = .005). No significant differences in gastrointestinal side effects were reported; however, less nausea or vomiting was reported in the hydrocodone group (P = .23). Central nervous system side effects (sedation or lightheadedness) were reported in six hydrocodone/acetaminophen patients compared with 16 codeine/acetaminophen patients (P less than .005). In addition, no hydrocodone/acetaminophen patients reported inadequate analgesia compared with six codeine/acetaminophen patients (P less than .05). CONCLUSION: Although pain scores were not significantly different, hydrocodone may be a more effective analgesic than codeine in acute musculoskeletal pain, as demonstrated by significantly fewer treatment failures. Central nervous system side effects are less common with hydrocodone than with codeine.

Acetaminophen↗

PubMed1994

Analgesic efficacy of flurbiprofen in comparison with acetaminophen, acetaminophen plus codeine, and placebo after impacted third molar removal.

PURPOSE: The analgesic efficacy of 50 and 100 mg flurbiprofen was compared with acetaminophen 650 mg, acetaminophen 650 mg plus codeine 60 mg, and placebo. PATIENTS AND METHODS: Subjects undergoing the surgical removal of impacted third molars were randomly administered one of the five treatments after the onset of moderate to severe postoperative pain. Pain intensity, pain relief, and side effects were evaluated for 6 hours after drug administration. RESULTS: Both doses of flurbiprofen resulted in significant analgesia in comparison with placebo, acetaminophen, and acetaminophen plus codeine as measured by pain intensity difference, pain relief, and global evaluation. The greatest incidence of side effects occurred in the group receiving acetaminophen plus codeine, and the fewest side effects were reported by subjects administered flurbiprofen. CONCLUSION: The results of this study indicate that flurbiprofen is more effective and causes fewer effects than acetaminophen and codeine when used for post-operative dental pain, in ambulatory patients.

Acetaminophen↗

PubMed1998

Simultaneous determination of codeine and its seven metabolites in plasma and urine by high-performance liquid chromatography with ultraviolet and electrochemical detection.

A sensitive and selective high-performance liquid chromatography method has been developed for the measurement of codeine and its seven metabolites, norcodeine, morphine, normorphine, codeine-6-glucuronide, morphine-6-glucuronide, morphine-3-glucuronide and norcodeine glucuronide, in plasma and urine. The compounds were recovered from plasma and urine using solid-phase extraction with C18 cartridges and separated on a reversed-phase C8 column with a mobile phase consisting of 77% buffer (5 mM sodium phosphate monobasic and 0.70 mM sodium dodecyl sulfate, pH 2.35) and 23% acetonitrile. Codeine, norcodeine, codeine-6-glucuronide, norcodeine glucuronide and morphine-3-glucuronide were detected by ultraviolet detection at 214 nm, with a detection limit of 0.02 nmol/ml for each compound in plasma. Morphine-6-glucuronide, normorphine and morphine were monitored by electrochemical detection at 350 mV, with a detection limit of 0.003 nmol/ml for each compound in plasma. The assay showed good reproducibility and accuracy using external standardization. The recovery and inter-day variation for all compounds in plasma samples were 63.40-77.90% and 3.49-16.77% (R.S.D.) and while in urine were 64.98-90.13% and 2.93-9.96% (R.S.D.), respectively.

Chromatography, High Pressure Liquid↗

PubMed1999

Fully automated analytical method for codeine quantification in human plasma using on-line solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.

A simple, sensitive and fully automated analytical method for the analysis of codeine in human plasma is presented. Samples are added with oxycodone, used as internal standard (I.S.), and directly loaded in the autosampler tray. An on-line sample clean-up system based on solid-phase extraction (SPE) cartridges (Bond-Elut C2, 20 mg) and value switching (Prospekt) is used. Isocratic elution improved reproducibility and allowed the recirculation of the mobile phase. A Hypersil BDS C18, 3 microns, 10 x 0.46 cm column was used and detection was done by UV monitoring at 212 nm. Retention times of norcodeine (codeine metabolite), codeine and oxycodone (I.S.) were 5.5, 6.4 and 9.1 min, respectively. Morphine was left to elute in the chromatographic front. Detection limit for codeine was 0.5 microgram l-1 and inter-assay precision (expressed as relative standard deviation) and accuracy (expressed as relative error) measured at 2 micrograms l-1 were 5.03% and 1.82%. Calibration range was 2-140 micrograms l-1.

Automation↗

PubMed2001

LC method for the analysis of acetylsalicylic acid, caffeine and codeine phosphate in pharmaceutical preparations.

An accurate, simple, reproducible and sensitive method for the determination of acetylsalicylic acid, caffeine and codeine phosphate has been developed and validated. Acetylsalicylic acid, caffeine and codeine phosphate were separated using a microBondapack C(8) column by isocratic elution with flow rate 1.0 ml/min. The mobile phase composition was 125/125/250/0.5 (v/v) isopropyl alcohol, acetonitrile, water and o-phosphoric acid. The samples were detected at 215 nm using photo-diode array detector. The linear range of detection for acetylsalicylic acid, caffeine and codeine phosphate were between 0.40 and 1000, 0.25 and 250, and 0.48 and 96 microg/ml, respectively. The linearity, range, selectivity, system performance parameters, precision, accuracy, and ruggedness for acetylsalicylic acid, caffeine and codeine phosphate were also shown to have acceptable values.

Analgesics, Opioid↗

PubMed2002

Determination of codeine and its metabolite in human urine by CE with amperometric detection.

The amperometric detection of codeine and its metabolite, morphine following capillary zone electrophoretic separation is described. A carbon-disk electrode used as working electrode for two analytes exhibited a good response at 0.90 V (vs. Ag/AgCl). The optimal conditions of separation and detection were pH 8.4 phosphate buffer solution (0.06 mol x l(-1)), 12 kV for the separation voltage, sample injection at 12 kV for 10 s. The linear ranges were from 3.1 x 10(-7) to 2.5 x 10(-5) mol x l(-1) for codeine and 1.9 x 10(-7) to 1.5 x 10(-5) x mol l(-1) for morphine with a correlation coefficient of 0.9996 and 0.9999, respectively. The detection limits for codeine and morphine were 1.6 x 10(-7) and 6.8 x 10(-8) x mol l(-1). The method developed was successfully applied to the determination of codeine and its metabolite, morphine in the human urine without any other sample pretreatment except filtration, and the results were satisfactory.

Analgesics, Opioid↗

PubMedDate not supplied

Ketorolac versus acetaminophen-codeine in the emergency department treatment of acute low back pain.

Acute low back pain is a common problem in the emergency department (ED). Effective management of acute pain enhances early rehabilitation and recovery. Given the importance of inflammatory mediators in pain generation and the adverse effects associated with opioids, it is logical to expect that a non-opioid agent with antiinflammatory and analgesic properties would provide excellent analgesia with fewer adverse effects. This double-blind, randomized, multicenter clinical trial, performed in six university and community hospital EDs, compares the analgesic efficacy and adverse effects of ketorolac to those of acetaminophen-codeine in ED patients with acute musculoskeletal low back pain. Our hypothesis was that ketorolac would provide superior analgesia with fewer adverse effects. One hundred twenty-three patients with acute low back pain were randomized to receive ketorolac (KET, N = 63) or acetaminophen-codeine (ACOD, N = 60). Most (79%) were males, and the mean age was 34.5 years. After baseline clinical assessment, patients were treated with ketorolac (10 mg every 4 to 6 h as needed, up to four daily doses) or acetaminophen-codeine (600 mg-60 mg, respectively, every 4 to 6 h as needed, up to six daily doses) and followed for one week. Pain intensity was assessed on visual analogue and categorical scales. Functional capacity, overall pain relief, and overall medication rating were assessed on categorical scales. Adverse events were documented. Primary outcomes included: 1) Pain intensity differences, based on visual analogue scores, for the 0 to 6 h treatment phase. 2) Incidence of adverse events. Secondary outcomes included analgesic efficacy, functional capacity, and overall subjective drug evaluation at one week. Both drugs provided substantial pain relief, with maximal effect 2.2 h after oral dosing. There were no significant differences in analgesic efficacy, functional capacity, or overall pain relief between the two groups. Sixteen patients (10 KET vs. 6 ACOD, NS) withdrew prematurely because of drug inefficacy. Patients in the ACOD group reported significantly more adverse drug events and serious adverse drug events. Seven patients--all in the ACOD group--withdrew from the study because of adverse drug events. Based on comparable efficacy and a superior adverse event profile, ketorolac was preferable to acetaminophen with codeine for the treatment of acute low back pain in the ED.

Acetaminophen↗

PubMed1975

Synthesis of thebaine and oripavine from codeine and morphine.

A practical synthesis of thebaine and oripavine has been developed from codeine and morphine, respectively. Attempts to use a codeinone intermediate gave poor yields; however, methylation of the potassium salt of codeine to give codeine methyl ether followed by oxidation with gamma-MnO2 gave thebaine in 67% yield from codeine. Similarly, the potassium salt of the di-O-anion of morphine was selectively alkylated to give morphine 6-methyl ether (heterocodeine) in better than 90% yield. Hetercodeine was then acetylated and oxidized to oripavine 3-acetate which was hydrolyzed to give oripavine in 73% yield from morphine.

Codeine↗

PubMed1982

Analgesic effects of oral nalbuphine and codeine in patients with postoperative pain.

Efficacy and safety of oral nalbuphine in doses of 15 and 45 mg were compared with those of the standard oral analgesic codeine in single doses of 30 and 90 mg in 153 patients with acute postoperative pain; data on 20 more patients were excluded because they received potentially interfering medications. All patients had pain ranging from moderate to severe in intensity and most had severe pain related to orthopedic procedures or trauma. Estimates of relative potency showed that nalbuphine was three times as potent as codeine. The most common side effect was sedation, which was greatest in patients who received the higher doses of codeine and nalbuphine. The effects of oral nalbuphine are much like those of oral codeine in patients with acute postoperative pain.

Adolescent↗

PubMed1987

The additive analgesic efficacy of acetaminophen, 1000 mg, and codeine, 60 mg, in dental pain.

In a double-blind, randomized, single-dose trial the analgesic contribution of acetaminophen, 1000 mg, and codeine, 60 mg, was determined. The study was a 2 X 2 factorial experiment in which 120 patients suffering from pain as a result of oral surgery rated their pain intensity and pain relief for up to 5 hours after a single dose of one of: 1000 mg acetaminophen, 60 mg codeine, 1000 mg acetaminophen plus 60 mg codeine, or placebo. The factorial analysis showed that both 1000 mg acetaminophen and 60 mg codeine made a statistically significant (P less than 0.05) contribution to the analgesic effectiveness of the combination on all measures of efficacy (sum of pain intensity differences, largest pain intensity difference, total pain relief, largest pain relief, and time to remedication). The incidence of adverse effects did not appear to differ among the treatments, including placebo.

Acetaminophen↗

PubMed1988

Association of pain relief with drug side effects in postherpetic neuralgia: a single-dose study of clonidine, codeine, ibuprofen, and placebo.

In a randomized, double-blind crossover study, 40 patients with postherpetic neuralgia were given single oral doses of clonidine, 0.2 mg, codeine, 120 mg, ibuprofen, 800 mg, or inert placebo. Pain relief and side effects were recorded for 6 hours. Patients reported significantly more relief after clonidine than after the other three treatments. Codeine and ibuprofen were ineffective. Sedation, dizziness, and other side effects were more frequent after clonidine (74%) or codeine (69%) than after placebo (36%) or ibuprofen (28%). Reported pain relief was greater during trials in which side effects were present. A single, mild side effect was associated with as much additional pain relief as multiple, severe side effects. Clonidine's superiority to codeine, which had a similar incidence of side effects, argues for a specific analgesic effect. In addition, side effects may have contributed to clonidine analgesia, perhaps by suggesting to patients that they had received a potent drug.

Aged↗

PubMed1988

Analgesic effect of picenadol, codeine, and placebo in patients with postoperative pain.

A double-blind, parallel study was conducted to evaluate the analgesic effect and safety of a single 25 mg oral dose of picenadol, a centrally acting analgesic, and to compare it with a 60 mg dose of codeine and a placebo in patients with postoperative pain. Two sites using similar protocols enrolled a total of 178 inpatients with postoperative pain. Pain intensity, relief, and adverse experiences were then measured for up to 6 hours after administration of the test medications. Both picenadol and codeine were significantly more effective than placebo in reducing pain intensity (mean sum of pain intensity difference scores: picenadol 5.21, codeine 5.19, and placebo 2.82) and increasing total relief (mean total pain relief: picenadol 10.21, codeine 11.07, and placebo 6.96). Adverse experience profiles were similar among the three treatment groups.

Adult↗

PubMed1998

Maintenance treatment of opiate addicts in Germany with medications containing codeine--results of a follow-up study.

AIMS: Outpatient maintenance treatment of opiate addicts with codeine/dihydrocodeine is a common approach in the treatment of drug addicts in Germany. This study was carried out to assess possible benefits of codeine maintenance in terms of patients' health stabilization, social rehabilitation and drug consumption. DESIGN: Three-year follow-up study. SETTING: Three practices of substituting physicians in large-city areas in Germany. PARTICIPANTS: Of a random sample of 297 people attending for opiate outpatient treatment in 1993, 199 were successfully followed up 3 years later. MEASUREMENTS: Measures of health, living conditions, employment, criminal activities and drug use were collected at baseline and follow-up. The data were based on standardized interviews and medical examinations by the attending doctors as well as on questionnaires from the patients. FINDINGS: Based on a 67%-follow-up rate, after 3 years of codeine maintenance there was improvement in general health and mental problems. The living and working situation remained more or less unchanged and stabilized at a satisfactory level. The same applies to the consumption of drugs. CONCLUSION: The patients' progress shown in this study was comparable to that achieved by methadone maintenance in similar geographical regions. Codeine has a weaker pharmacological effects and our results suggest that codeine maintenance treatment deserves more attention and controlled trials to assess the benefits compared with methadone (or other opioids).

Adult↗

PubMed1992

Opioid analgesics and the risk of hip fracture in the elderly: codeine and propoxyphene.

We studied the risk of hip fracture in elderly persons receiving prescriptions for two commonly prescribed opioid analgesics--codeine and propoxyphene. Using automated prescription and hospitalization data, we identified 4,500 residents of Saskatchewan, Canada, aged 65 or older, who sustained a hip fracture between 1977 and 1985, and 24,041 age- and sex-matched controls. Compared to nonusers, the relative risk (95% CI) of hip fracture in current users of codeine or propoxyphene was 1.6 (1.4-1.9). There was no difference between relative risks of fracture among current users of codeine [1.6 (1.3-1.9)] and propoxyphene [1.6 (1.2-2.2)]. In new users of these opioids, the relative risk of fracture was 2.2 (1.7-2.8), compared to 1.3 (1.0-1.6) in users who received at least one additional prescription for codeine or propoxyphene in the 90-day period prior to the index date. Concurrent users of these opioids and psychotropic drugs (sedatives, antidepressants, or antipsychotics) had a risk of fracture 2.6 (2.0-3.4) times that of nonusers of either drug class. Review of a sample of medical records for 701 cases suggested this finding was not due to confounding by body mass, ambulatory status, functional status, or dementia. Given the essential role of opioids in the management of pain in geriatric practice, further study is needed to determine the psychomotor effects of opioid analgesics in older adults.

Age Factors↗