Photodegradation products of propranolol: The structures and pharmacological studies

Life Sciences

Volumn 78, Issue 4, 2005, Pages 357-365

  Uwai, Koji ^a   Tani, Marie ^a   Ohtake, Yosuke ^a   Abe, Shinya ^a   Maruko, Akiko ^a   Chiba, Takashi ^b   Hamaya, Yoshiro ^b   Ohkubo, Yasuhito ^a   Takeshita, Mitsuhiro ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b Japan Community Healthcare Organization Sendai Hospital   (Japan)

Author keywords

adrenergic receptor; Photodegradation; Propranolol; Receptor binding

Indexed keywords

1 NAPHTHOL; BETA ADRENERGIC RECEPTOR; N ACETYLPROPRANOLOL; N FORMYLPROPRANOLOL; PROPRANOLOL; PROPRANOLOL DERIVATIVE; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ANIMAL EXPERIMENT; ARTICLE; CEREBELLUM CORTEX; CONTROLLED STUDY; DRUG BINDING; DRUG PACKAGING; DRUG STABILITY; DRUG STRUCTURE; MALE; MOUSE; NEUROTOXICITY; NONHUMAN; PHOTODEGRADATION; SPECTROSCOPY; SYNTHESIS;

ADRENERGIC BETA-ANTAGONISTS; ANIMALS; CEREBRAL CORTEX; DRUG STABILITY; LETHAL DOSE 50; MALE; MICE; MICE, INBRED STRAINS; NAPHTHOLS; PHOTOCHEMISTRY; PHOTOLYSIS; PROPRANOLOL; RATS; RATS, WISTAR; RECEPTORS, ADRENERGIC, BETA; ULTRAVIOLET RAYS;

ANIMALIA;

EID: 27744553157     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2005.04.033     Document Type: Article

References (28)

1. V. Andrisano, R. Gotti, A. Leoni, and V. Cavrini Photodegradation studies on atenolol by liquid chromatography Journal of Pharmaceutical and Biomedical Analysis 21 4 1999 851 857
2. J.M. Aubry, B. Mandard-Cazin, M. Rougee, and R.V. Bensasson Kinetic studies of singlet oxygen [4 + 2]-cycloadditions with cyclic 1,3-dienes in 28 solvents Journal of the American Chemical Society 117 36 1995 9159 9164
3. J.A. Berson, and E. Brown Dihydropyridines: II. The photochemical disproportionation of 4-(2′-nitrophenyl)-1,4-dihydropyridines Journal of the American Chemical Society 77 1995 447 450
4. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Analytical Biochemistry 72 1976 248 254
5. Chen C.S., 1994. Enzymic preparation of optically active propanolol and β-adrenergic blockers using esterase. United States Patent No. 5334534.
6. C.S. Chen, D.M. Gou, W.R. Shieh, and Y.C. Liu Biocatalytic resolution of dl-propranolol. A successful example of computeraided substrate design Tetrahedron 49 16 1993 3281 3290
7. T.-W. Chiou, C.-C. Chang, C.-T. Lai, and D.-F. Tai Kinetic resolution of propranolol by a lipase-catalyzed N-acetylation Bioorganic and Medicinal Chemistry Letters 7 4 1997 433 436
8. M. Comtet, and H.D. Mettee Photoisomerization of azulene Molecular Photochemistry 2 1 1970 63 66
9. M. Cordoba-Borrego, M. Cordoba-Diaz, and D. Cordoba-Diaz Validation of a high-performance liquid chromatographic method for the determination of norfloxacin and its application to stability studies (photo-stability study of norfloxacin) Journal of Pharmaceutical and Biomedical Analysis 18 6 1999 919 926
10. G.H. Dewar, J.K. Kwakye, R.T. Parfitt, and R. Sibson Optical purity determination by NMR: use of chiral lanthanide shift reagents and a base line technique Journal of Pharmaceutical Sciences 71 7 1982 802 806
11. J.S. Grundy, R. Kherani, and R.T. Foster Photostability determination of commercially available nifedipine oral dosage formulations Journal of Pharmaceutical and Biomedical Analysis 12 12 1994 1529 1535
12. H. Hart, and A. Oku Octamethylnaphthalene 1,4-endoperoxide Journal of the Chemical Society, Chemical Communications 5 1972 254 255
13. B.B. Hoffman, and R.J. Lefkowitz Catecholamines, sympathomimetic drugs, and adrenergic receptor antagonists L.S. Goodman A. Gilman J.G. Hardman L.E. Limbird Goodman and Gilman's the Pharmacological Basis of Therapeutics 9th ed. 1996 McGraw-Hill New York 199 248
14. J.T. Litchfield Jr., and F. Wilcoxon A simplified method of evaluating dose-effect experiments Journal of Pharmacology and Experimental Therapeutics 96 1949 99 113
15. B. Malinowska, K. Kiec-Kononowicz, K. Flau, G. Godlewski, H. Kozlowska, M. Kathmann, and E. Schlicker Atypical cardiostimulant beta-adrenoceptor in the rat heart: stereoselective antagonism by bupranolol but lack of effect by some bupranolol analogues British Journal of Pharmacology 139 8 2003 1548 1554
16. B. Marciniec, and M. Ogrodowczyk Photo- and radiostability of some 1,4-dihydropyridine derivatives in the solid state Acta Poloniae Pharmaceutica 60 2 2003 151 155
17. V.D. Marinkovic, D. Agbaba, K. Karljikovic-Rajic, S. Vladimirov, and J.M. Nedeljkovic Photochemical degradation of solid-state nisoldipine monitored by HPLC Journal of Pharmaceutical and Biomedical Analysis 32 4-5 2003 929 935
18. M. Matsumoto, K. Kojima, H. Nagano, S. Matsubara, and T. Yokota Photostability and biological activity of fluoroquinolones substituted at the 8 position after UV irradiation Antimicrobial Agents and Chemotherapy 36 8 1992 1715 1719
19. W.L. Nelson, and R.B. Walker The structure of propranolol hemisuccinate Research Communications in Chemical Pathology and Pharmacology 22 3 1978 435 445
20. J. Olmsted III Photoisomerization of azulene Molecular Photochemistry 1 3 1969 331 336
21. g) carriers for biological media Journal of Photochemistry and Photobiology. B, Biology 36 1 1996 31 39
22. P. Pietta, A. Rava, and P. Biondi High-performance liquid chromatography of nifedipine, its metabolites and photochemical degradation products Journal of Chromatography 210 3 1981 516 521
23. G. Pohlers, H. Dreeskamp, and S. Grimme The mechanism of photochemical C-O or C-S bond cleavage in aryl(thio)ethers Journal of Photochemistry and Photobiology. A, Chemistry 95 1 1996 41 49
24. H. Salomies Oxidation of β-bloking agents V. Light-influenced oxidation of propranolol and its glycol with N-bromosuccinimide Acta Pharmaceutica Suecica 24 4 1987 193 198
25. M. Shamsipur, B. Hemmateenejad, M. Akhond, K. Javidnia, and R. Miri A study of the photo-degradation kinetics of nifedipine by multivariate curve resolution analysis Journal of Pharmaceutical and Biomedical Analysis 31 5 2003 1013 1019
26. S. Sortino, S. Petralia, F. Boscà, and M. Miranda Irreversible photo-oxidation of propranolol triggered by self-photogenerated singlet molecular oxygen Photochemical and Photobiological Sciences 1 2 2002 136 140
27. H. Suzuki, S. Fujiwara, S. Kondo, and I. Sugimoto Determination of nifedipine in human plasma by high-performance liquid chromatography with electrochemical detection Journal of Chromatography 341 2 1985 341 347
28. Y. Yoshida, E. Sato, and R. Moroi Photodegradation products of levofloxacin in aqueous solution Arzneimittel-Forschung 43 5 1993 601 606