Navegar

Colección

Datos Estadísticas

Artículo

Garcia, C.V.; Nudelman, N.S.; Steppe, M.; Schapoval, E.E.S. "Structural elucidation of rabeprazole sodium photodegradation products" (2008) Journal of Pharmaceutical and Biomedical Analysis. 46(1):88-93
La versión final de este artículo es de uso interno de la institución.
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Rabeprazole sodium is a proton pump inhibitor, used in acid-related disorders, like peptic ulcers and gastroesophageal reflux. It is known to be an acid-labile drug, however, few data about its stability under other factors are available. The aim of this work was to study the photodegradation of rabeprazole, to determine its kinetics and to elucidate the structures of the main degradation products. UVC-254 nm and metal-halide lamps were used. The analysis of the samples was carried out by HPLC. When the drug was in methanol solution, one main degradation product was formed; the degradation rate followed zero-order kinetics. The 1H and 13C NMR spectroscopic determinations revealed the product was the benzimidazolone. Another isolated product was identified as benzimidazole. The latter was confirmed against an authentic sample. A third photodegradation product was identified as the [4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl]methanol, by 1H and 13C NMR of the reaction mixture in chloroform-d. When powdered commercial tablets were exposed to UVC irradiation, they showed the same degradation products along with other unidentified, which appeared as traces; the degradation rate was slower than in solution. The intact tablets were stable after 50 days of exposition to the same light source. © 2007 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Structural elucidation of rabeprazole sodium photodegradation products
Autor:Garcia, C.V.; Nudelman, N.S.; Steppe, M.; Schapoval, E.E.S.
Filiación:Universidade Federal do Rio Grande do Sul, Programa de Pós-Graduação em Ciências Farmacêuticas, Faculdade de Farmácia., Av. Ipiranga, 2752, Porto Alegre, RS CEP 90610-000, Brazil
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, piso 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Benzimidazole; Kinetics; Photodegradation products; Photostability; Proton pump inhibitor; Rabeprazole; benzimidazole; chloroform; halide; methanol; rabeprazole; article; chemical reaction; drug isolation; drug stability; drug structure; enzyme kinetics; high performance liquid chromatography; nuclear magnetic resonance; photodegradation; priority journal; tablet; ultraviolet C radiation; 2-Pyridinylmethylsulfinylbenzimidazoles; Benzimidazoles; Carbon Isotopes; Chromatography, High Pressure Liquid; Color; Drug Contamination; Drug Stability; Hydrochloric Acid; Hydrogen Peroxide; Kinetics; Magnetic Resonance Spectroscopy; Methanol; Molecular Conformation; Powders; Pyridines; Solutions; Stereoisomerism; Tablets; Temperature; Time Factors; Tritium; Ultraviolet Rays
Año:2008
Volumen:46
Número:1
Página de inicio:88
Página de fin:93
DOI: http://dx.doi.org/10.1016/j.jpba.2007.09.002
Título revista:Journal of Pharmaceutical and Biomedical Analysis
Título revista abreviado:J. Pharm. Biomed. Anal.
ISSN:07317085
CODEN:JPBAD
CAS:benzimidazole, 51-17-2; chloroform, 67-66-3; methanol, 67-56-1; rabeprazole, 117976-89-3, 117976-90-6; 2-Pyridinylmethylsulfinylbenzimidazoles; benzimidazole, 51-17-2; Benzimidazoles; benzimidazolone, 20662-53-7; Carbon Isotopes; Hydrochloric Acid, 7647-01-0; Hydrogen Peroxide, 7722-84-1; Methanol, 67-56-1; Powders; Pyridines; rabeprazole, 117976-90-6; Solutions; Tablets; Tritium, 10028-17-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07317085_v46_n1_p88_Garcia

Referencias:

  • Carswel, C.I., Goa, K.L., (2001) Drugs, 61, pp. 2327-2356
  • Bart, J., Hahne, W., (2002) Aliment. Pharmacol. Ther., 16, pp. 31-33
  • Nakai, H., Shimamura, Y., Kanazama, T., Yasuda, S., Kayano, M., Chrom, J., (1994) B: Biomed. Appl., 660, pp. 211-220
  • Takakuwa, S., Chiku, S., Nakata, H., Yuzuiha, T., Mano, N., Asakawa, N., Chrom, J., (1995) B: Biomed. Appl., 673, pp. 113-122
  • Mano, N., Oda, Y., Takakuwa, S., Chiku, S., Nakata, H., Asakawa, N., (1996) J. Pharm. Sci., 85, pp. 903-907
  • Singh, S.S., Jain, M., Shah, H., Gupta, S., Thakker, P., Shah, R., Lohray, B., (2004) J. Chromatogr. B, 813, pp. 247-254
  • Uno, T., Yasui-Furukori, N., Shimizu, M., Sugawara, K., Tateishi, T., (2005) J. Chromatogr. B, 824, pp. 238-243
  • Ramakrishna, N.V., Vishwottam, K.N., Wishu, S., Koteshwara, M., Kumar, S., (2005) J. Chromatogr. B, 816, pp. 209-214
  • Zhang, Y., Chen, X., Gu, Q., Zhong, D., (2004) Anal. Chim. Acta, 523, pp. 171-175
  • Huang, J., Xu, Y., Gao, S., Rui, L., Guo, Q., (2005) Rapid Commun. Mass Spectrom., 19, pp. 2321-2324
  • Tivesten, A., Folestad, S., Schönbacher, V., Svensson, K., (1999) Chromatographia, 49, pp. S7-S11
  • El-Gindy, A., El-Yazby, F., Maher, M.M., (2003) J. Pharm. Biomed. Anal., 31, pp. 229-242
  • Radi, A., El-Ghany, N., Wahdan, T., (2004) II Farmaco, 59, pp. 515-518
  • Garcia, C.V., Paim, C.S., Steppe, M., (2004) J. AOAC Int., 87, pp. 842-846
  • Garcia, C.V., Sippel, J., Sfair, L., Garcia, S.S., Jablonski, A., Steppe, M., Schapoval, E.E.S., (2005) J. AOAC Int., 88, pp. 1081-1085
  • Garcia, C.V., Sippel, J., Steppe, M., Schapoval, E.E.S., (2006) Anal. Lett., 39, pp. 341-348
  • Nozal, M.J., Toríbio, L., Bernal, J., Alonso, C., Jimenez, J., (2004) J. Sep. Sci., 27, pp. 1023-1029
  • Toríbio, L., Nozal, M.J., Bernal, J.L., Jiménez, A., (2005) J. Chromatogr. A, 1091, pp. 118-123
  • Miura, M., Tada, H., Satoh, S., Habuchi, T., Suzuki, T., (2006) J. Pharm. Biomed. Anal., 41, pp. 565-570
  • Rao, R.N., Raju, A.N., Nagaraju, D., (2006) Talanta, 70, pp. 805-810
  • Garcia, C.V., Paim, C.S., Steppe, M., Schapoval, E.E.S., (2006) J. Pharm. Biomed. Anal., 41, pp. 833-837
  • Reddy, G.M., Bhaskar, B.V., Reddy, P.P., Sudhakar, P., Babu, J.M., Vyas, K., Reddy, P., Mukkanti, K., (2007) J. Pharm. Biomed. Anal., 43, pp. 1262-1269
  • Mathew, M., Das Gupta, V., Bailey, R., (1995) Drug Dev. Ind. Pharm., 21, pp. 965-971
  • Radi, A., (2002) Microchem. J., 73, pp. 349-354
  • Qaisi, A., Tutunji, M., Tutunji, L., (2006) J. Pharm. Sci., 95, pp. 384-391
  • Kommanaboyina, B., Rhodes, C.T., (1999) Drug Dev. Ind. Pharm., 25, pp. 857-868
  • Vadas, E.B., (2000) Remington: The Science and Practice of Pharmacy. 20th ed., pp. 980-985. , Genaro A.R. (Ed), Lippincott Williams & Wilkins, Philadelphia
  • Nudelman, N.S., Gallardo Cabrera, C., (2002) J. Pharm. Sci., 91, pp. 1274-1286
  • DellaGreca, M., Iesce, M.R., Previtera, L., Rubino, M., Temussi, F., Brigante, M., (2006) Chemosphere, 63, pp. 1087-1093
  • Tonnesen, H.H., (2001) Int. J. Pharm., 225, pp. 1-14

Citas:

---------- APA ----------
Garcia, C.V., Nudelman, N.S., Steppe, M. & Schapoval, E.E.S. (2008) . Structural elucidation of rabeprazole sodium photodegradation products. Journal of Pharmaceutical and Biomedical Analysis, 46(1), 88-93.
http://dx.doi.org/10.1016/j.jpba.2007.09.002
---------- CHICAGO ----------
Garcia, C.V., Nudelman, N.S., Steppe, M., Schapoval, E.E.S. "Structural elucidation of rabeprazole sodium photodegradation products" . Journal of Pharmaceutical and Biomedical Analysis 46, no. 1 (2008) : 88-93.
http://dx.doi.org/10.1016/j.jpba.2007.09.002
---------- MLA ----------
Garcia, C.V., Nudelman, N.S., Steppe, M., Schapoval, E.E.S. "Structural elucidation of rabeprazole sodium photodegradation products" . Journal of Pharmaceutical and Biomedical Analysis, vol. 46, no. 1, 2008, pp. 88-93.
http://dx.doi.org/10.1016/j.jpba.2007.09.002
---------- VANCOUVER ----------
Garcia, C.V., Nudelman, N.S., Steppe, M., Schapoval, E.E.S. Structural elucidation of rabeprazole sodium photodegradation products. J. Pharm. Biomed. Anal. 2008;46(1):88-93.
http://dx.doi.org/10.1016/j.jpba.2007.09.002