Isolation and structural elucidation of degradation products of alprazolam: Photostability studies of alprazolam tablets

Accelerated thermal, hydrolytic, and photochemical degradations of alprazolam were performed under several reaction conditions. The stress studies revealed the photolability of the drug as the most adverse stability factor; the main photodegradation products were isolated and properly characterized...

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Autor principal: Nudelman, N.S
Otros Autores: Cabrera, C.G
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: John Wiley and Sons Inc. 2002
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024 7 |2 cas  |a alprazolam, 28981-97-7 
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100 1 |a Nudelman, N.S. 
245 1 0 |a Isolation and structural elucidation of degradation products of alprazolam: Photostability studies of alprazolam tablets 
260 |b John Wiley and Sons Inc.  |c 2002 
270 1 0 |m Nudelman, N.S.; Depto. Quimica Organica, Fac. de Ciencias Exact. y Naturales, Universidad de Buenos Aires, Pab. II, P.3 Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Laihanen, N., Muttonen, E., Laaksonen, M., Solubility and intrinsic dissolution rate of alprazolam crystal modifications (1996) Pharm Dev Technol, 14, pp. 373-380 
504 |a Dresser, G.K., Spence, J.D., Bailey, D.G., Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition (2000) Clin Pharmacokinet, 38 (1), pp. 41-57 
504 |a Gommans, J., Hijzen, T.H., Maes, R.A., Olivier, B., Discriminative stimulus properties of alprazolam (2000) Psychopharmacology, 148 (2), pp. 146-152 
504 |a Yuan, R., Flockhart, D.A., Balian, J.D., Pharmacokinetic and pharmacodynamic consequences of metabolism-based drug interactions with alprazolam, midazolam, and triazolam (1999) J Clin Pharmacol, 39 (11), pp. 1109-1125 
504 |a Santagostino, G., Cucchi, M.L., Frattini, P., Zerbi, F., Di Paolo, E., Preda, S., Corona, G.L., The influence of alprazolam on the monoaminergic neurotransmitter systems in dysthymic patients: Relationship to clinical response (1998) Pharmacopsychiatry, 31 (4), pp. 131-136 
504 |a Greenblatt, D.J., Javaid, J.I., Locniskar, A., Harmatz, J.S., Shader, R.I., Gas chromatographic analysis of alprazolam in plasma: Replicability, stability and specificity (1990) J Chromatogr, 534, pp. 202-207 
504 |a Greenblatt, D.J., Divoll, M., Moschitto, L.J., Shader, R.I., Electron-capture gas chromatographic analysis of the triazolobenzodiazepines alprazolam and triazolam (1981) J Chromatogr, 225, pp. 202-207 
504 |a Hall, M.A., Robinson, A., Brissie, R.M., High-performance liquid chromatography of alprazolam in postmortem blood using solid phase extraction (1995) J Anal Toxicol, 19, pp. 511-513 
504 |a Schmith, V.D., Cox, S.R., Zemaitis, M.A., Kroboth, P.D., New high-performance liquid chromatographic method for the determination of alprazolam and its metabolites in serum: Instability of 4-hydroxyalprazolam (1991) J Chromatogr, 568, pp. 253-260 
504 |a Hold, K.M., Crouch, D.J., Rollins, D.E., Wilkins, D.G., Maes, R.A., Detection of alprazolam in hair by negative ion chemical ionization mass spectrometry (1997) Forensic Sci Int, 84, pp. 201-209 
504 |a Crouch, D.J., Rollins, D.E., Canfield, D.E., Andrenyak, D.M., Schulties, J.E., Quantitation of alprazolam and α-hydroxyalprazolam in human plasma using liquid chromatography electrospray ionization MS-MS (1999) J Anal Toxicol, 23, pp. 479-485 
504 |a Hold, K.M., Rollins, D.E., Crouch, D.J., Wilkins, D.G., Canfield, D.V., Maes, R.A., Determination of alprazolam and α-hydroxyalprazolam in human plasma by gas chromatography/negative-ion chemical ionization mass spectrometry (1996) J Mass Spectrom, 31, pp. 1033-1038 
504 |a Konishi, M., Hirai, K., Mori, Y., Kinetics and mechanism of the equilibrium reaction of triazolam in aqueous solution (1982) J Pharm Sci, 71, pp. 1328-1334 
504 |a Andersin, R., Mesilaakso, M., Photochemical decomposition of midazolam. IV. Study of pH-dependent stability by high-performance liquid chromatography (1995) J Pharm Biomed Anal, 13, pp. 667-670 
504 |a Cho, M.J., Scahill, T.A., Hester, J.B., Kinetics and equilibrium of the reversible alprazolam ring-opening reaction (1983) J Pharm Sci, 72, pp. 356-362 
504 |a Nudelman, N.S., Waisbaum, R.G., Kinetic study of the reaction of 2-amino-5-chlorobenzophenone with HC1 in MeOH-H2O (1997) J Phys Org Chem, 10, pp. 97-106 
504 |a Nudelman, N.S., Waisbaum, R.G., Isolation and structure elucidation of novel products of the acidic degradation of diazepam (1995) J Pharm Sci, 84, pp. 208-211 
504 |a Nudelman, N.S., Waisbaum, R.G., Acid hydrolysis of diazepam: Kinetic study of the reactions of 2-(N-methylamino)-5-chlorobenzophenone, with HCl in MeOH-H2O (1995) J Pharm Sci, 84, pp. 998-1004. , and refs. therein 
504 |a Nudelman, N.S., Gallardo, C., Factores que afectan estabilidad de alprazolam: Elucidación estructural de los principales productos de degradación (1999) Vitae, 6, pp. 29-40 
504 |a Nudelman, N.S., Waisbaum, R.G., Gallardo, C., Stability studies of benzodiazepines: Solvolysis and photodegradation (1998) Atualidades Fisico Quim Org, pp. 478-497 
504 |a Allen, L.E., Erickson, M.A., Stability of alprazolam, chloroquine phosphate, cisapride, enalapril maleate and hydralazine hydrochloride in extemporaneously compounded oral liquids (1998) Am J Health Syst Pharm, 55, pp. 1915-1920 
504 |a Caira, M.R., Easter, B., Honiball, S., Horne, A., Nassimbeni, L.R., Structure and thermal stability of alprazolam and selected solvates (1995) J Pharm Sci, 84, pp. 1379-1384 
504 |a Stemm, N.L., Skoug, J.W., Robins, R.H., Gradient high performance liquid chromatography assay for degradation products of adinazolam mesylate in a sustained release tablet formulation (1995) Pharm Res, 12, pp. 738-745 
504 |a Kanwar, A.J., Gupta, R., Das Metha, S., Photosensitivity due to alprazolam (1990) Dermatologica, 181, p. 75 
504 |a Harth, Y., Rapoport, M., Photosensitivity associated with antipsychotics, antidepressant and anxiolytics (1996) Drug Saf, 14, pp. 252-259 
504 |a Reid, C.G., Photosensitivity: Not a picture of health (1995) Can Pharm J, 128, pp. 31-56 
504 |a Tonnesen, H.H., Introduction: Photostability testing of drug formulations - Why and how? (1996) Photostability of drugs and drug formulations, pp. 1-7. , Tonnesen HH, editors. London: Taylor & Francis 
504 |a Piechocki, J.T., Selecting the right source for pharmaceutical photostability testing (1998) Drugs: Photochemistry and photostability, pp. 247-271. , Albini A, Fasani E, editors. Cambridge: Royal Society of Chemistry 
504 |a (1996) Photostability testing of new drug sustances and products, , November 
504 |a (1997) Fed Regist, 62, p. 27115 
504 |a (1998) Guidance for industry: Stability testing of drug substances and drug product, draft guidance, , June 
504 |a Valvini, S.C., Industrial stability testing in the United States and computerization of stability data (2000) Drug stability, principles and practices, 3rd ed., pp. 515-552. , Carstensen JT, Rhodes CT, editors. New York: Marcel Dekker 
504 |a Moore, D.E., Standardization of photodegradation studies and kinetic treatment of photochemical reaction (1996) Photostability of drugs and drug formulations, pp. 65-66. , Tonnesen HH, editor. London: Taylor & Francis 
504 |a Hong, D.D., Shah, M., Development and validation of HPLC stability-indicating assays (2000) Drug stability, principles and practices, 3rd ed., pp. 329-384. , Carstensen JT, Rhodes CT, editors. New York: Marcel Dekker 
504 |a Anderson, N.H., Photostability testing: Design and interpretation of tests on drug substances and dosage forms (1996) Photostability of drugs and drug formulations, pp. 305-321. , Tonnesen HH, editors. London: Taylor & Francis 
504 |a Photostability testing (2000) Pharmacopeial Forum, 26, pp. 384-387 
504 |a Cho, M.J., Sethy, V.H., Haynes, L.C., Sequentially labile water-soluble prodrugs of alprazolam (1986) J Med Chem, 29, pp. 1346-1350 
504 |a Jimenez, R.M., Dominguez, E., Bahia, D., Alonso, R.M., Vicent, F., On the mechanism of hydrolysis of the triazolobenzodiazepine, triazolam, spectroscopic study (1987) J Heterocycl Chem, 24, p. 421 
504 |a Greenhill, J.V., Is the photodecomposition of drugs predictable? (1996) Photostability of drugs and drug formulations, pp. 83-110. , Tonnesen HH, editor. London: Taylor & Francis 
504 |a Moore, D.E., Roberts-Thomson, S., Zhen, D., Duke, C.C., Photochemical studies on the anti-inflammatory drug diclofenac (1990) Photochem Photobiol, 52, pp. 685-690 
504 |a Schoonderwoerd, S.A., Beijerssbergen van Henegouwen, G.M., Van Belkum, S., In vivo photodegradation of chlorpromazine (1989) Photochem Photobiol, 50, p. 659 
504 |a Greenhill, J.V., McLelland, M.A., Photodecomposition of drugs (1990) Progress in medicinal chemistry, 27, pp. 51-121. , Ellis GP, West GB, editors. Amsterdam: Elsevier 
520 3 |a Accelerated thermal, hydrolytic, and photochemical degradations of alprazolam were performed under several reaction conditions. The stress studies revealed the photolability of the drug as the most adverse stability factor; the main photodegradation products were isolated and properly characterized as: triazolaminoquinoleine; 5-chloro-[5-methyl-4H-1,2,4-triazol-4-yl]benzophenone, and 1-methyl-6-phenyl-4h-s-triazo- [4,3-α][1,4]benzodiazepinone. Accelerated pH-dependent studies show that the photoinstability increases as the pH decreases; at pH 9.0, photodegradation does not occur, therefore, the photochemical degradation of alprazolam was performed in buffered solutions at pH 2.0 and 3.6. The higher rate of reaction was observed at pH = 2.0; consequently, acidic conditions should be avoided and appropriate light protection is recommended during the drug-development process, storage, and handling. The main degradation route for alprazolam tablets is also photochemical. © 2002 Wiley-Liss, Inc.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: National Research Council 
536 |a Detalles de la financiación: Cancer Genomics Centre 
536 |a Detalles de la financiación: Departamento Administrativo de Ciencia, Tecnología e Innovación, COLCIENCIAS 
536 |a Detalles de la financiación: Agency for Science, Technology and Research 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: CGC is a grateful recipient of a COLCIENCIAS fellowship. The authors are indebted to Gador Lab. for the provision of AL and other drugs. Financial support from the University of Buenos Aires, the CONICET (National Research Council), and the Agency for the Promotion of Science and Technology from Argentine is acknowledged. 
593 |a Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, P.3 Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a ALPRAZOLAM 
690 1 0 |a ALPRAZOLAM PHOTODEGRADATION PRODUCTS 
690 1 0 |a ALPRAZOLAM STABILITY 
690 1 0 |a PHOTOCHEMICAL DEGRADATION 
690 1 0 |a TRIAZOLOBENZODIAZEPINES 
690 1 0 |a ALPRAZOLAM 
690 1 0 |a AMINOQUINOLINE DERIVATIVE 
690 1 0 |a BENZODIAZEPINE DERIVATIVE 
690 1 0 |a BENZOPHENONE DERIVATIVE 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMICAL REACTION KINETICS 
690 1 0 |a DRUG DEGRADATION 
690 1 0 |a DRUG ISOLATION 
690 1 0 |a DRUG STABILITY 
690 1 0 |a DRUG STORAGE 
690 1 0 |a HYDROLYSIS 
690 1 0 |a PHOTOCHEMISTRY 
690 1 0 |a STRUCTURE ANALYSIS 
690 1 0 |a TABLET 
690 1 0 |a THERMOSTABILITY 
650 1 7 |2 spines  |a PH 
700 1 |a Cabrera, C.G. 
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