Determination of photostability and photodegradation products of indomethacin in aqueous media

Journal of Pharmaceutical and Biomedical Analysis

Volumn 56, Issue 4, 2011, Pages 678-683

  Temussi, Fabio ^a   Cermola, Flavio ^a   Dellagreca, Marina ^a   Iesce, M Rosaria ^a   Passananti, Monica ^a   Previtera, Lucio ^a   Zarrelli, Armando ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Arylalkanoic acids; Indomethacin; Mesolytic cleavage; Photo oxidation; Photodecarboxylation

Indexed keywords

ALCOHOL; ALDEHYDE; INDOMETACIN; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; DECARBOXYLATION; DRUG STABILITY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; OXYGENATION; PHOTOCHEMISTRY; PHOTODEGRADATION; PRIORITY JOURNAL;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DRUG STABILITY; HUMANS; HYDROLYSIS; INDOMETHACIN; OXIDATION-REDUCTION; PHARMACOKINETICS; PHOTOLYSIS; PHOTOSENSITIVITY DISORDERS; SOLVENTS; SUNLIGHT; ULTRAVIOLET RAYS; WATER POLLUTANTS, CHEMICAL;

EID: 84860413487     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.07.005     Document Type: Article

References (22)

1. Ekiz-Gücer N., Reisch J. Photochemical studies, 58. Photostability of indomethacin in the crystalline state. Pharm. Acta Helv. 1991, 66:66-67.
2. Weedon A.C., Wong D.F. The photochemistry of indomethacin. J. Photochem. Photobiol. A 1991, 61:27-33.
3. Dabestani R., Sik R.H., Davis D.G., Dubay G., Chignell C.F. Spectroscopic studies of cutaneous photosensitizing agents. XVIII. Indomethacin. Photochem. Photobiol. 1993, 58:367-373.
4. Wu A.-B., Cheng H.-W., Hu C.-M., Chen F.-A., Chou T.-C., Chen C.-Y. Photolysis of Indomethacin in Methanol. Tetrahedron Lett. 1997, 38:621-622.
5. Moore D.E., Chappuis P.P. A comparative study of the photochemistry of the non-steroidal anti-inflammatory drugs, naproxen, benoxaprofen and indomethacin. Photochem. Photobiol. 1988, 47:173-180.
6. Pawelczyk E., Knitter B., Knitter K. Kinetics of drug decomposition. Part 50: Graphic method for calculation of zero-order rate constants of sequential reaction of indomethacine photodegradation. Pharmazie 1977, 32:483-485.
7. Musa K.A.K., Eriksson L.A. Theoretical investigation of NSAID photodegradation mechanisms. Quantum Biochem. 2010, 2:805-834.
8. Nayak P. Commonly used photosensitizing medications: their adverse effects and precautions to be considered. Int. J. Pharm. Sci. 2010, 4:135-140.
9. De Guidi G., Ragusa S., Cambria M.T., Belvedere A., Catalfo A., Cambria A. Photosensitizing effect of some nonsteroidal antiinflammatory drugs on natural and artificial membranes: dependence on phospholipid composition. Chem. Res. Toxicol. 2005, 18:204-212.
10. Bosca F., Marin M.L., Miranda M.A. Photodecarboxylation of acids and lactones: antiinflammatory drugs. CRC Handbook of Photochemistry and Photobiology 2004, For a review, CRC Press, Boca Raton, pp. 64-1-64-10. 2nd ed. W. Horspool, F. Lenci (Eds.).
11. Stern R.S., Bigby M. An expanded profile of cutaneous reactions to nonsteroidal anti-inflammatory drugs. Reports to a specialty-based system for spontaneous reporting of adverse reactions to drugs. J. Am. Med. Assoc. (JAMA) 1984, 252:1433-1437.
12. Onoue S., Tsuda Y. Analytical studies on the prediction of photosensitive/phototoxic potential of pharmaceutical substances. Pharm. Res. 2006, 23:156-164.
13. Comeau F., Surette C., Brun G.L., Losier R. The occurrence of acidic drugs and caffeine in sewage effluents and receiving waters from three coastal watersheds in Atlantic Canada. Sci. Total Environ. 2008, 396:132-146.
14. Quintero B., Miranda M.A. Mechanisms of photosensitization induced by drugs: a general survey. Ars Pharmaceutica 2000, 41:27-46.
15. Torisu K., Kobayashi K., Iwahashi M., Egashira H., Nakai Y., Okada Y., Nanbu F., Ohuchida S., Nakai H., Toda M. Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead. Eur. J. Med. Chem. 2005, 40:505-519.
16. Dulin D., Mill T. Development and evaluation of sunlight actinometers. Environ. Sci. Technol. 1982, 16:815-820.
17. Pitchumani K., Madhavan D. Induced diastereoselectivity in photodecarboxylation reactions. CRC Handbook of Photochemistry and Photobiology 2004, CRC Press, Boca Raton, pp. 65-1-65-14. 2nd ed. W. Horspool, F. Lenci (Eds.).
18. Bosca F., Miranda M.A., Vano L., Vargas F. New photodegradation pathways for Naproxen, a phototoxic non-steroidal anti-inflammatory drug. J. Photochem. Photobiol. A 1990, 54:131-134.
19. Sobolewski A.L., Domcke W. Photoinduced charge separation in indole-water clusters. Chem. Phys. Lett. 2000, 329:130-137.
20. McGimpsey W.G., Goerner H. Photoionization of indole, N-methylindole and tryptophan in aqueous solution upon excitation at 193nm. Photochem. Photobiol. 1996, 64:501-509.
21. Mudry C.A., Frasca A.R. Photo-oxidation of indole derivatives. Tetrahedron 1973, 29:603-613.
22. Oldroyd D.L., Weedon A.C. Solvent- and wavelength-dependent photochemistry of N-benzoylindole and N-ethoxycarbonylindole. J. Photochem. Photobiol. A. 1991, 57:207-216.