Über die Umwandlung von Thebain in Oxycodeinon und dessen Derivate

Freund, Martin; Speyer, Edmund

doi:10.1002/prac.19160940112

Cited by 36 publications

(11 citation statements)

References 9 publications

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“…Opioids are the primary analgesics for the treatment of severe medical, traumatic, and surgical pain. Oxycodone hydrochloride, a semisynthetic opioid analgesic, has been in clinical use since 1917 13 . In adults, oxycodone has demonstrated less pharmacokinetic variability than has morphine 14 .…”

mentioning

confidence: 99%

Population Pharmacokinetics of Oxycodone in Children 6 Months to 7 Years Old

El‐Tahtawy

Kokki

Reidenberg

2006

The Journal of Clinical Pharma

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Young children are often undertreated for pain. One barrier to effective pain treatment is understanding the pharmacokinetic behavior of analgesics in this age group. Oxycodone is a commonly prescribed opioid for severe pain, yet little is known about its pharmacokinetics in young children. This article used population pharmacokinetic modeling to synthesize pharmacokinetic data from several studies into a model. A single population model that described the observed pharmacokinetics was developed. The combined data were best described with a 2-compartment linear model with different first-order absorption rates depending on route of administration. Weight was found to significantly influence both clearance (CL) and volume of distribution (Vd). The following model adequately describes the population pharmacokinetic profile of oxycodone where absolute bioavailability (F) is estimated for each administration route: CL/F=55x(body weight/70)0.87; V/F=86x(body weight/70)1.16. The interindividual coefficients of variation in CL and Vd were 20.2 and 19.7%, respectively. This finding confirms that the allometric scaling using the above model explained most of the variability in exposure observed among children. This model confirms using a weight-based dose for oxycodone without adjustment for age between 6 months and 7 years and is valuable for evaluating dosing schedules and dosing routes.

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confidence: 99%

Population Pharmacokinetics of Oxycodone in Children 6 Months to 7 Years Old

El‐Tahtawy

Kokki

Reidenberg

2006

The Journal of Clinical Pharma

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“…Figure 4 shows the mass spectrum of the TMS derivative which gave a molecular ion of 459 mle (315 mle, underivatized, data not shown), a base peak at 229 mle, and a fragmentation pattern indistinguishable from that of authentic mnaterial. Similar purification of putative biological norcodeine by HPLC (elution time 17.8 min) afforded about 700 ,ug of the pure 4. Gas chromatography and electron impact mass spectrum of purified 140HCOD obtained from pooled cultures of S. griseus ATCC 10137 incubated with codeine.…”

Section: Resultsmentioning

confidence: 99%

Identification of transformation products arising from bacterial oxidation of codeine by Streptomyces griseus

Kunz¹,

Reddy²,

Vatvars³

1985

Appl Environ Microbiol

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14-Hydroxycodeine and norcodeine were rigorously identified as products arising from codeine oxidation by Streptomyces griseus ATCC 10137. Both products were routinely detected in extracted culture filtrates after growth of cells in the presence of codeine for 1 week. Under these conditions, about 4 mol% of the codeine starting material was consumed, with norcodeine and 14-hydroxycodeine representing the only identifiable transformation products (molar ratio, 4:1, respectively). Extraction of a series of culture filtrates and purification of the pooled metabolites by thin-layer and high-pressure liquid chromatography led to the isolation of both biological products, the structures of which were verified by high-resolution mass spectrometry and proton nuclear magnetic resonance spectroscopy. The identities of both biological products were further confirmed by comparison of their spectral properties with those of authentic standards. This is the first report providing structural evidence for the biological formation of 14-hydroxycodeine from codeine and of codeine oxidation by S. griseus.

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“…The unusual behavior of similarly constituted tertiary N-methylethanolamines (3)(4)(5) is borne out, if only in a negative sense, by the work of others (6, 7) who described the demethylation of 14-acetoxycodeinone (VII) and 14-acetoxydihydrocodeinone (VIII) but not of the 14hydroxy analogs (IX and X) from which they were prepared. The nature of the impediment by the hydroxyl group i s suggested by studies of other investigators (8-10) on alkyl cyanates, by previous studies in these laboratories on epoxy ether (IV) formation from I(13-15) and on the chemistry of the hydroxyl group in V, IX, and X (3)(4)(5)(6)(7)(8)(9), and by the character of the reaction mixture and products obtained by treatment of V with CNBr.…”

Section: Sirmentioning

confidence: 85%