Isolation and structure elucidation of novel products of the acidic degradation of diazepam

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The acidic degradation of diazepam in methanolic aqueous solution has been investigated. Apart from the known degradation products, 2‐(N‐methylamino)‐5‐chlorobenzophenone and glycine, produced by the hydrolytic cleavage of the benzodiazepinone ring, five novel products were isolated and fully charac...

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Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: de Waisbaum, R.G
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1995
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-0028809094 
024 7 |2 cas  |a Diazepam, 439-14-5 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
100 1 |a Nudelman, N.S. 
245 1 0 |a Isolation and structure elucidation of novel products of the acidic degradation of diazepam 
260 |c 1995 
270 1 0 |m Nudelman, N.S.; Depto. Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, P. 3, Buenos Aires, 1428, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Sternbach, L.H., (1978) Progress in Drug Research, 22, p. 229. , Jucker, E., Birkhauser, Basel 
504 |a Fryer, R.I., (1983) The Benzodiazepines: from Molecular Biology to Clinical Practice, , Costa, E., Raven, New York 
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504 |a Gilman, N.W., Rosen, P., Earley, J.V., Cook, C., Todaro, L.J., (1990) J. Am. Chem. Soc., 112, p. 3969 
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504 |a Nudelman, N.S., Waisbaum, R.G., (1975), p. 478. , Il Farmaco; , p. 488. , (b) Il Farmaco p; Inotsume, N., Nakano, M., (1980) J. Pharm. Sci., 69, p. 1331 
504 |a Maulding, H.V., Nazareno, J.P., Pearson, J.E., Michaelis, A.F., (1975) J. Pharm. Sci., 64, p. 277 
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504 |a Han, W.W., Yakatan, G.J., Maness, D.D., (1976) J. Pharm. Sci., 65, p. 1198 
504 |a Nudelman, N.S., (1975) Stability of Drugs, , El Ateneo, Buenos Aires, Argentina 
504 |a Connors, K.A., Amidon, G.L., Stella, V.J., (1979) Chemical Stability of Pharmaceuticals: A Handbook for Pharmacists, p. 1986. , Wiley & Sons, NY, 2nd ed 
504 |a Bronxton, T.J., Ryan, T., Morrison, S.R., (1984) Aust. J. Chem., 37, p. 1896 
504 |a Bronxton, T.J., Morrison, S.R., (1986) Aust. J. Chem., 38, p. 1037 
504 |a Bronxton, J.T., Wright, S., Micellar catalysis of organic reactions. 18. Basic hydrolysis of diazepam and some N-alkyl derivatives of nitrazepam (1986) The Journal of Organic Chemistry, 51, p. 2965 
504 |a Gaete, G., Muñoz, M.T., Castro, D., Pezoa, R., Arancibia, A., (1986) An. Real Acad. Farm., 52, p. 481 
504 |a Nudelman, N.S., Marder, M., Gurevich, A., (1993), p. 229. , J. Chem. Soc., Perkin Trans. 2; Nudelman, N.S., Doctorovich, F., (1990) Mag. Res. Chem., 28, p. 576 
504 |a Nudelman, N., Lewkowicz, E., Furlong, J.J.P., (1993) J. Org. Chem., 58, p. 1847 
504 |a Sternbach, L.H., Fryer, I., Metlesics, W., Sach, G., Stempel, J., (1962) J. Org. Chem., 27, p. 3781 
504 |a Nudelman, N.S., Socolovsky, S.S., Waisbaum, R.G., (1982) An. Quim., 78, p. 145 
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504 |a Gros, E., Gruñeiro, E.M., (1971) J. Org. Chem., 36, p. 1166 
504 |a Adams, J.H., Gupta, P., Khan, L.S., Watt, R.A., Intramolecular cyclisation of 2-aminobenzophenones; a new 9-acridone synthesis (1976) Journal of the Chemical Society, Perkin Transactions 1, 1, p. 2089 
504 |a Nudelman, N.S., Waisbaum, R.G., Mass spectra ofo-aminobenzophenones (1978) Organic Mass Spectrometry, 13, p. 61 
504 |a March, J., (1992) Advanced Organic Chemistry. Reactions, Mechanisms and Structures, , 4th ed., Wiley‐Interscience, NY 
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520 3 |a The acidic degradation of diazepam in methanolic aqueous solution has been investigated. Apart from the known degradation products, 2‐(N‐methylamino)‐5‐chlorobenzophenone and glycine, produced by the hydrolytic cleavage of the benzodiazepinone ring, five novel products were isolated and fully characterized by their spectroscopic features and independent synthesis. Substituted 2‐amino‐3,5‐dichlorobenzophenones and 2,4‐dichloroacridinones were found, the formation of which in the reaction media is mechanistically intriguing. The role of these unexpected products in accelerated studies of diazepam stability is discussed. Copyright © 1995 Wiley‐Liss, Inc., A Wiley Company  |l eng 
536 |a Detalles de la financiación: National Research Council 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: The authors thank to Roche Labs for providing samples of diazepam. Financial support from the National Research Council (CONICET), and the Universidad de Buenos Aires is acknowledged. 
593 |a Depto. Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, P. 3, Buenos Aires, 1428, Argentina 
690 1 0 |a 5 CHLORO 2 (METHYLAMINO)BENZOPHENONE 
690 1 0 |a BENZOPHENONE DERIVATIVE 
690 1 0 |a DIAZEPAM 
690 1 0 |a GLYCINE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ANXIETY NEUROSIS 
690 1 0 |a ARTICLE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DRUG DEGRADATION 
690 1 0 |a DRUG DETERMINATION 
690 1 0 |a DRUG HYDROLYSIS 
690 1 0 |a DRUG ISOLATION 
690 1 0 |a DRUG STABILITY 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a SEIZURE 
690 1 0 |a SLEEP DISORDER 
690 1 0 |a WITHDRAWAL SYNDROME 
690 1 0 |a CHROMATOGRAPHY, THIN LAYER 
690 1 0 |a DIAZEPAM 
690 1 0 |a DRUG STABILITY 
690 1 0 |a HYDROLYSIS 
690 1 0 |a MAGNETIC RESONANCE SPECTROSCOPY 
690 1 0 |a SPECTROPHOTOMETRY, INFRARED 
690 1 0 |a SPECTROPHOTOMETRY, ULTRAVIOLET 
690 1 0 |a SPECTRUM ANALYSIS, MASS 
690 1 0 |a SUPPORT, NON-U.S. GOV'T 
700 1 |a de Waisbaum, R.G. 
773 0 |d 1995  |g v. 84  |h pp. 208-211  |k n. 2  |p J. Pharm. Sci.  |x 00223549  |w (AR-BaUEN)CENRE-807  |t Journal of Pharmaceutical Sciences 
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856 4 0 |u https://doi.org/10.1002/jps.2600840217  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00223549_v84_n2_p208_Nudelman  |y Handle 
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999 |c 73435 

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