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2. Hydrogen-deuterium (H/D) exchange reaction of acebutolol hydrochloride in D₂O and CD₃OD solution

Author

H, Guesmi, J Ben, Kraim, A, Alatrache, and U, Holzgrabe

Subjects
Methanol, Solvents, Deuterium Oxide, Deuterium, Acebutolol, Hydrogen
Abstract

H/D exchange reactions can be observed by NMR spectroscopy of acebutolol (ACE). The results obtained showed deuterium incorporation at α-posi t ion of the carbonyl group of acebutolol, when using deuterium oxide or deuterated methanol as deuterium source and solvent. The spontaneous deuteration is proceeded by the following pathway CH₃→CH₂D→CHD→CD₃, through a keto-enol tautomerization reaction. Furthermore, LC-MS / QTOF analyses have confirmed the proposed H/D exchange. In order to reduce the time of total deuteration observed at the acetyl group alkaline catalysts were employed.

Published
2022

3. [Pharmacokinetics and pharmacodynamics of antibiotics in intensive care]

Author

F, Sörgel, R, Höhl, R, Glaser, C, Stelzer, M, Munz, M, Vormittag, M, Kinzig, J, Bulitta, C, Landersdorfer, A, Junger, M, Christ, M, Wilhelm, and U, Holzgrabe

Subjects
Male, Critical Care, Metabolic Clearance Rate, Microbial Sensitivity Tests, Penicillins, Mass Spectrometry, Anti-Bacterial Agents, Intensive Care Units, Reference Values, Vancomycin, Humans, Female, Drug Monitoring, Half-Life, Protein Binding
Abstract

Optimized dosage regimens of antibiotics have remained obscure since their introduction. During the last two decades pharmacokinetic(PK)-pharmacodynamic(PD) relationships, originally established in animal experiments, have been increasingly used in patients. The action of betalactams is believed to be governed by the time the plasma concentration is above the minimum inhibitory concentration (MIC). Aminoglycosides act as planned when the peak concentration is a multiple of the MIC and vancomycin seems to work best when the area under the plasma vs. time curve (AUC) to MIC has a certain ratio. Clinicians should be aware that these relationships can only be an indication in which direction dosing should go. Larger studies with sufficiently high numbers of patients and particularly severely sick patients are needed to prove the concepts. In times where all antibiotics can be measured with new technologies, the introduction of therapeutic drug monitoring (TDM) is suggested for ICUs (Intensive Care Unit). The idea of a central lab for TDM of antibiotics such as PEAK (Paul Ehrlich Antibiotika Konzentrationsmessung) is supported.

Published
2016

4. Validation and application of an HPLC-CAD-TOF/MS method for identification and quantification of pharmaceutical counterions

Author

D, Ilko, C J, Nap, U, Holzgrabe, and S, Almeling

Subjects
Aerosols, Ions, Pharmaceutical Preparations, Limit of Detection, Reference Standards, Drug Contamination, Sensitivity and Specificity, Chromatography, High Pressure Liquid, Mass Spectrometry
Abstract

A generic approach for the analysis of counterions of pharmaceutical reference substances, which are established by the laboratory department of the European Pharmacopoeia (Ph. Eur.), was developed. A mixed-mode chromatography method using charged aerosol detection (CAD) published by Zhang et al. separating 25 commonly used pharmaceutical counterions was selected for this purpose. The method was validated in terms of specificity, repeatability, limits of quantification (LOQs), linearity and range according to ICH guideline Q2(R1) and the Technical Guide for the Elaboration of Monographs of the Ph. Eur. Moreover, the applicability of the method for the purpose of counterion identification and quantification in drug substances as well as for the control of inorganic ions as impurities was demonstrated using selected examples of Ph. Eur. reference standards and other samples of substances for pharmaceutical use (e.g. cloxacillin sodium, somatostatin). It was shown that for identification purposes of the parent substance as well as organic ions the chromatographic system can easily be coupled to a mass selective detector without any modification.

Published
2015

5. Assisting drug dosing in pediatrics

Author

J Scheiber, A Pospiech, U Holzgrabe, P Högger, and M Zilker

Subjects
Psychiatry and Mental health, medicine.medical_specialty, business.industry, medicine, Drug dosing, Pharmacology (medical), General Medicine, Intensive care medicine, Psychiatry, business
Published
2014
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6. Possibilities and limitations of capillary electropherosis in pharmaceutical analysis

Author

C, Borst, F, Belal, and U, Holzgrabe

Subjects
Dibenzothiazepines, Electrophoresis, Capillary, Reproducibility of Results, Stereoisomerism, Mass Spectrometry, Quetiapine Fumarate, Pharmaceutical Preparations, Indicators and Reagents, Drug Contamination, Acids, Oxidation-Reduction, Chromatography, High Pressure Liquid, Antipsychotic Agents, Tablets
Abstract

Capillary electropherosis (CE) has been proved to be an important alternative to high-performance liquid chromatography (HPLC) in pharmaceutical analysis. However, when it comes to the analysis of compounds, e.g. impurities or metabolites, of very different polarity and water solubility CE and the related techniques come to its limits. This is demonstrated for the antipsychotic drug quetiapine and its impurities. A nonaqueous capillary electrophoresis (NACE) method was developed using a background electrolyte (BGE) composed of ammonium acetate dissolved in a mixture of acetonitrile and methanol including acetic acid to protonate the substances. The NACE method gave an excellent separation of all components. Since the conductivity of the BGE used in the NACE method is quite low and problems with current occurred, an additional aqueous capillary zone electrophoresis (CZE) method was developed for quetiapine and the two water soluble derivatives, using phosphate buffer as BGE. The method was validated with regard to repeatability and limit of detection.

Published
2013

7. How to evaluate the separation efficiency of CZE methods?

Author

C, Büttner-Merz and U, Holzgrabe

Subjects
Pharmacopoeias as Topic, Quality Control, Models, Chemical, Tetracyclines, Electrophoresis, Capillary, Reproducibility of Results, Drug Contamination, Anti-Bacterial Agents
Abstract

In trying to estimate the separation efficiency of Capillary Electrophoresis (CE) methods, the resolution (RS), the number of theoretical plates (N) and the peak-to-valley ratio (p/v) are often used assessment criteria. This study demonstrates that these criteria are not as suitable to describe the separation efficiency in case of Capillary Zone Electrophoresis (CZE) methods as they are for Liquid Chromatography (LC) methods. The investigations were performed by means of a validated CZE method for the evaluation of tetracyclines and their related substances. Four impurities of tetracycline hydrochloride are described in the European Pharmacopoeia. Three were found in the sample used for our investigations, i.e. epi-tetracycline formed by keto-enol-tautomerism, anhydrotetracyclin and epi-anhydrotetracyline. It could be shown that higher values of these assessment criteria like RS do not necessarily represent better separation. Thus, a discussion on the usefulness of separation selectivity and efficiency as assessment criteria for capillary electrophoresis as well as on the introduction of additional parameters is needed.

Published
2011

10. Prediction of the oversulphated chondroitin sulphate contamination of unfractionated heparin by ATR-IR spectrophotometry

Author

J, Norwig, T, Beyer, D, Brinz, U, Holzgrabe, M, Diller, and D, Manns

Subjects
Analysis of Variance, Principal Component Analysis, Magnetic Resonance Spectroscopy, Models, Statistical, Spectrophotometry, Infrared, Heparin, Sulfates, Calibration, Chondroitin Sulfates, Dermatan Sulfate, Least-Squares Analysis, Drug Contamination
Abstract

The detection of a contamination of heparin with oversulphated chondroitin sulphate (OSCS) was first analysed in an unfractionated heparin batch supplied to the US API-market in April 2006. OSCS is a semi-synthetic derivative of the natural occuring glycosaminoglycan chondroitin sulphate. Moreover some spectroscopic characteristics of the substance overlap with those of heparin, so that the infrared (IR) spectra are visually difficult to distinguish whereas (1)H-NMR (Nuclear Magnetic Resonance) spectroscopy or capillary electrophoresis (CE) provides identification by a simple visual inspection of either the spectrum or the electropherogram respectively. However, applying special tools of Multivariate Data Analysis (MVA) to the IR spectra an identification of the contaminated samples is possible. In detail a rapid Attenuation Total Reflectance-Infrared (ATR-IR) measurement was selected, which does not require any sample preparation. The result (contaminated or not contaminated) is predicted within a few minutes. A method transfer to mobile ATR-IR spectrometers seems to be possible. The analysis is based on the fact that the fingerprint of the OSCS IR spectrum (1st derivative) complies with a theoretically calculated principal component in the MVA.

Published
2009

11. Determination of Oversulphated Chondroitin Sulphate and Dermatan Sulphate in unfractionated heparin by (1)H-NMR - Collaborative study for quantification and analytical determination of LoD

Author

I, McEwen, B, Mulloy, E, Hellwig, L, Kozerski, T, Beyer, U, Holzgrabe, R, Wanko, J-M, Spieser, and A, Rodomonte

Subjects
Pharmacopoeias as Topic, Magnetic Resonance Spectroscopy, Molecular Structure, Heparin, Chondroitin Sulfates, Sodium, Dermatan Sulfate, Water, Deuterium, Europe, Solutions, Polysaccharides, Calcium, Drug Contamination
Abstract

Oversulphated Chondroitin Sulphate (OSCS) and Dermatan Sulphate (DS) in unfractionated heparins can be identified by nuclear magnetic resonance spectrometry (NMR). The limit of detection (LoD) of OSCS is 0.1% relative to the heparin content. This LoD is obtained at a signal-to-noise ratio (S/N) of 2000:1 of the heparin methyl signal. Quantification is best obtained by comparing peak heights of the OSCS and heparin methyl signals. Reproducibility of less than 10% relative standard deviation (RSD) has been obtained. The accuracy of quantification was good.

Published
2009

12. Analysis of Drugs

Author

B. W. K. Diehl and U. Holzgrabe

Subjects
Chemistry, Computational chemistry, Stereochemistry, Orphenadrine, medicine, Nuclear magnetic resonance spectroscopy, medicine.drug
Published
2007
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13. NMR of Body Fluids

Author

U. Holzgrabe

Subjects
Chromatography, Chemistry, Blood plasma, Nuclear magnetic resonance spectroscopy, Urine
Abstract

Summary This chapter contains sections titled: NMR of Urine — Studies of Metabolism NMR of Bile, Blood Plasma, Cerebrospinal and Seminal Fluids LC NMR Hyphenation

Published
2007
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15. pH-Dependent NMR Measurements

Author

G. Hägele and U. Holzgrabe

Subjects
Ciprofloxacin, Stereochemistry, Chemistry, medicine, Ph dependent, Norfloxacin, medicine.drug, Nuclear chemistry
Published
2007
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17. Determination of the impurity profile of adenosine by means of ion-pair reversed-phase chromatography

Author

S, Kopec, S, Almeling, and U, Holzgrabe

Subjects
Pharmacopoeias as Topic, Quality Control, Adenosine, Guanosine, Adenine, Temperature, Reproducibility of Results, Inosine, Europe, Quaternary Ammonium Compounds, Pharmaceutical Preparations, Technology, Pharmaceutical, Chromatography, Thin Layer, Drug Contamination, Uridine, Chromatography, High Pressure Liquid
Abstract

Production processes of adenosine include condensation of ribose and adenine by means of chemical or biochemical processes, as well as fermentation. Nowadays, adenosine is commonly produced by alkaline hydrolysis of yeast ribonucleic acid, often in the presence of calcium or lead ions, followed by chromatographic separation of the obtained nucleosides adenosine, cytidine, guanosine and uridine. The current Ph. Eur. monograph for adenosine describes a TLC method for determination of related substances that limits the impurities to 1 per cent. To ensure the quality of adenosine, it is proposed to replace the TLC method by a more sensitive and selective HPLC method, in accordance with the current policy for control of impurities as defined by the Ph. Eur. Commission. An HPLC separation system, originally proposed by the USP, using ion-pair reversed-phase chromatography in combination with tetrabutylammonium hydrogen sulphate as an ion-pair reagent, has been examined for its suitability to limit guanosine, inosine, uridine and adenine. This article describes the experiments as regards the choice of the most suitable commercial column to obtain an appropriate separation, the column temperature, the establishment of a relevant system suitability criterion, and the determination of correction factors for the individual impurities.

Published
2007

18. Batch variability of bacitracin: HPLC versus MEKC

Author

C, Weber, S, Matingen, and U, Holzgrabe

Subjects
Europe, Pharmacopoeias as Topic, Quality Control, Bacitracin, Drug Industry, Molecular Structure, Reproducibility of Results, Technology, Pharmaceutical, Drug Contamination, Chromatography, High Pressure Liquid, Chromatography, Micellar Electrokinetic Capillary
Abstract

10 lots of bacitracin collected from the European market were studied applying the European Pharmacopoeia HPLC method, and the results were compared to the findings of an orthogonal micellar electrokinetic chromatographic method. The latter method exhibited a far higher selectivity, resulting in a baseline separation of all bacitracin components, which could not be achieved with HPLC. Considering the contents of bacitracin A, B1, and B3, the lots could be organised into 2 groups. Due to high amounts of bacitracin B1 and B3, one lot did not fit into either group. All lots met the requirements of the European Pharmacopoeia.

Published
2007

21. [New hope for the cancer patient?]

Author

U, Holzgrabe and E, Bennack

Subjects
Nitrophenols, Sulfonamides, Proto-Oncogene Proteins c-bcl-2, Neoplasms, Biphenyl Compounds, Humans, Antineoplastic Agents, Piperazines, Genes, bcl-2
Published
2006

22. [Scientific pharmacy and homeopathy]

Author

U, Holzgrabe, M, Schubert-Zsilavecz, K, Mohr, and T, Dingermann

Subjects
Drug Therapy, Germany, Homeopathy, Pharmacy
Published
2006

27. Structure/activity relationships of M2 muscarinic allosteric modulators

Author

K, Mohr, C, Tränkle, and U, Holzgrabe

Subjects
Receptor, Muscarinic M2, Structure-Activity Relationship, Alcuronium, Allosteric Regulation, Alkanes, Animals, Humans, Signal Transduction
Abstract

Allosteric modulation of G protein-coupled receptors has been intensively studied at muscarinic acetylcholine receptors. Findings made with archetypal allosteric agents such as gallamine, alcuronium, and bis(ammonio)alkane-type agents revealed that binding of orthosteric ligands that attach to the acetylcholine site can be allosterically decreased or increased or left unaltered in a subtype-selective fashion. Analyses of structure/activity relationships (SARs) help to elucidate the molecular events underlying the allosteric action and they may pilot the development of new allosteric agents with improved properties and therapeutic perspectives. With a focus on SARs, this review illustrates the principles of muscarinic allosteric interactions, gives an overview of SARs in congeners of archetypal allosteric agents, and considers the topology of M(2) muscarinic allosteric interactions that are characterized by divergent binding modes.

Published
2003

28. Antitrypanosomal naphthylisoquinoline alkaloids and related compounds

Author

G, Bringmann, V, Hoerr, U, Holzgrabe, and A, Stich

Subjects
Molecular Weight, Structure-Activity Relationship, Alkaloids, Plants, Medicinal, Drug Design, Trypanosoma brucei brucei, Solvents, Animals, Indicators and Reagents, Isoquinolines, Trypanocidal Agents
Abstract

In view of the need to develop new drugs against human African trypanosomiasis, a series of naturally occurring naphthylisoquinoline alkaloids, axially chiral acetogenic products derived from tropical plants, have been investigated for their activity against Trypanosoma brucei brucei TC 221. Likewise compounds corresponding to the two molecular portions, the naphthalene and the isoquinoline parts were tested, as well as molecules related to the central biaryl core of the alkaloids. Among all compounds tested, the natural, genuine alkaloids themselves, in particular dioncophylline B with its biaryl system and a moderate number of free hydroxy functions, showed the highest activities. Our results demonstrate that naphthylisoquinoline alkaloids constitute an interesting novel class of antitrypanosomal compounds worth further optimization.

Published
2003

29. N1-phenyl substituted 4-quinolones of tuberculostatic activity

Author

U, Holzgrabe and M, Steinert

Subjects
Structure-Activity Relationship, 4-Quinolones, Anti-Infective Agents, Chlorocebus aethiops, Antitubercular Agents, Animals, Humans, Microbial Sensitivity Tests, Mycobacterium tuberculosis, Mycobacterium avium Complex, Vero Cells
Abstract

Various different substituted N1-phenyl-6-fluoro-7-piperazinyl-4-quinolone 3-carboxylates and the diazoniumtetrafluoroborate of sparfloxacin were tested for their ability to inhibit the growth of various Mycobacterium strains of different origin. The N1-p-hydroxylphenyl substituted compound 22 and the methoxyphenyl substituted compound missing the piperazine ring 12 were identified as promising candidates for the further development of an improved treatment of tuberculosis. In addition, compound 22 and the N1-p-fluorophenyl substituted analogue 4 were found to be active against Mycobacterium avium, which is often isolated from patients suffering from AIDS.

Published
2002

34. Enantioseparation of dihydropyridine derivatives by means of neutral and negatively charged beta-cyclodextrin derivatives using capillary electrophoresis

Author

T, Christians and U, Holzgrabe

Subjects
Cyclodextrins, Dihydropyridines, alpha-Cyclodextrins, Molecular Structure, beta-Cyclodextrins, Electrophoresis, Capillary, gamma-Cyclodextrins
Abstract

Employing capillary electrophoresis, the racemates of 29 acidic, neutral and basic dihydropyridines (DHPs) were separated by means of neutral and negatively charged cyclodextrins (CDs). Whereas the enantiomers of the acidic DHPs could be resolved with neutral CDs, mostly alpha- and beta-CD, the enantiomers of the neutral DHPs were only baseline-separated using the sulfobutyl ether-substituted beta-CD. Working in reversed polarity mode (detector at the anode) improved the peak shape and the resolution of the enantiomers. The racemates of the DHP bearing a secondary or tertiary amine function in the side chain at position 3 could be separated by using either the neutral gamma-CD or negatively charged CDs. The poor peak shape found with anionic CDs could be improved by the addition of methanol. The combination of gamma-CD and sulfated beta-CD allowed the detection of the minor enantiomer of lercanidipine (24) at less than 1% w/w.

Published
2001

38. D

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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39. A

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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40. H

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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41. I

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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42. C

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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43. G

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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44. F

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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45. B

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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46. K

Author

Franz von Bruchhausen, Eberhard Hackenthal, Siegfried Ebel, Ulrike Holzgrabe, August Wilhelm Frahm, M. Albinus, G. Amschler, E. von Angerer, null Arras-Reiter, P. Barth, W. Barthel, K. Bauer, P. Bauer, I. Baumann, J. Beckmann, W. Beil, J. Reitz, K. Binder, F. Bossle, F. Bracher, H. Bräunlich, E. Bretschneider, R. Brigelius-Flohé, K. Brinkmann, F. von Bruchhausen, A. Rüge, W. Christ, M. Cimbollek, R. Daniels, G. Dannhardt, H. Duchstein, S. Ebel, K. Eger, P. Eichhorn, U. Eiben, T. Erker, P. Felfe, A. Frahm, M. Frahm, V. Franke, K. Freundt, D. Geffken, U. Geis, E. Glusa, B. Göber, P. Gobina, W. Golder, M. Goppelt­Strübe, K. Götte, E. Gottstein, G. Greif, A. Grisk, M. Grosam, H. Gustmann, M. Gütschow, E. Hackenthal, A. Häfner, B. Haluszczynski, A. Harder, H. Häusler, D. Heber, M. Heidenreich, G. Heinemeyer, E. Heller, D. von Herrath, J. Hilfenhaus, H. Hoffmann, U. Hoffmann-Schollmayer, B. Hofmann, C. Holpert, U. Holzgrabe, U. Hübner-Steiner, M. Hug, E. Inkmann, A. Jördens, J. Jürgens, B. Kaiser, D. Kalbhen, H. Kemmler, P. Kisser, D. Kleinsorge, C. Klett, S. Klett, M. Klingmüller, H. Klöcking, A. Kramer, B. Krammer, M. Kreher, M. Krüger, M. Kuhn, D. Landsiedel-Maier, P. Lauven, J. Lehmann, M. Lehner, D. Leopoldt, A. Maurer, W. Meindl, K. Menges, P. Mes­singer, F. Meyer, W. Meyerhof, R. Morgenstern, U. Mühlhans, A. Müller, C. Müller, K. Müller, A. Mülsch, C. Nachtsheim, M. Neugebauer, W. Neupert, P. Nickel, P. Nuhn, B. Nürnberg, H. Oelschläger, J. Oertel, M. Oettel, R. Ott, T. Ott, T. Otzen, P. Pachaly, H. Pelzer, K. Petersen, R. Pick, M. Pickert, A. Pies, H. Priewer, O. Queckenberg, G. Radau, E. Reimann, J. Remien, M. Reuß, W. Reuß, J. Richter, P. Richter, K. Riecke, H. Rommelspacher, U. Rose, G. Roth, D. Rothley, G. Rücker, J. Schäfer, J. Schantl, H. Schlager, H. Schleinitz, W. Schlichter, M. Schmauß, H. Schmidhammer, G. Schmidt, T. Schmidt, H. Schmitt, J. Sehräder, T. Schulz, H. Schwilden, M. Serke, G. Skopp, G. Skorka, K. Smolinka, U. Speck, M. Spohn, R. Stahlmann, J. Stasch, C. Steffen, H. Stein, J. Steinmeyer, K. Stiefvater, G. Strippel, K. Surborg, U. Stürig, H. Szelényi, I. Szelényi, A. Täufel, R. Thieroff-Ekerdt, R. Troschütz, H. Ungeheuer, B. Unterhalt, E. Verspohl, S. Vogel, F. Volk, T. Vorwerk, J. Wallmann, H. Weber, M. Wenzel, M. Weyandt-Spangenberg, S. Wich, R. Wintersteiger, B. Wüst, and D. Youssef

Published
1999
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47. Stability of mono- and bisbenzyloxime ethers of the acetylcholinesterase reactivator TMB-4

Author

E, Inkmann, U, Holzgrabe, and K F, Hesse

Subjects
Cholinesterase Reactivators, Magnetic Resonance Spectroscopy, Spectrophotometry, Ultraviolet, Hydrogen-Ion Concentration, Trimedoxime, Crystallization
Abstract

Mono- and bisbenzyloxime ethers of the bispyridinium derivative TMB-4 (UNO, DUO) are potent allosteric modulators of the muscarinic receptor attracting clinical interest in case of organophosphate poisoning. In order to work out the stability of these compounds oximes, different oxime ethers and potential degradation products were synthesized and UV- and NMR-spectroscopically characterized. The process of degradation of all compounds was observed under stress conditions at varying pH-values and different temperatures by means of time-dependent NMR- und UV-measurements. The pyridinium aldoxime turned out to be rather stable, whereas the oxime ether and cyano derivatives convert to the pyridone at high pH-values and high temperature. The mechanism of degradation is discussed.

Published
1997

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