Phototransformation of Amlodipine in Aqueous Solution: Toxicity of the Drug and Its Photoproduct on Aquatic Organisms

DellaGreca, Marina; Iesce, Maria Rosaria; Isidori, Marina; Montanaro, Sara; Previtera, Lucio; Rubino, Maria

doi:https://doi.org/10.1155/2007/63459

International Journal of Photoenergy

On this page

Abstract References Copyright Related Articles

Research Article | Open Access

Volume 2007 | Article ID 063459 | https://doi.org/10.1155/2007/63459

Phototransformation of Amlodipine in Aqueous Solution: Toxicity of the Drug and Its Photoproduct on Aquatic Organisms

Marina DellaGreca,¹Maria Rosaria Iesce,¹Marina Isidori,²Sara Montanaro,¹Lucio Previtera,¹and Maria Rubino¹

Academic Editor: M. Bolte

Received11 May 2007

Revised26 Jul 2007

Accepted20 Sept 2007

Published19 Nov 2007

Abstract

The phototransformation of amlodipine in water was investigated under various conditions. A quantum yield ΦS2.2×10−4 and a half-life time t1/2 0.419 days were calculated when the drug in water (10−4 M) was exposed to sunlight. The only photoproduct found was its pyridine derivative. Formation of this product was explained on the basis of a radical cation intermediate. The acute and chronic toxicity of the drug and its photoproduct were evaluated on different organisms of the freshwater chain (Brachionus calyciflorus, Thamnocephalus platyurus, Daphnia magna, Ceriodaphnia dubia). The photoproduct exhibited a stronger toxic potential than the parent drug on the long time for C. dubia.

References

K. Kümmerer, “Pharmaceuticals in the environment-scope of the book and introduction,” in Pharmaceuticals in the Environment: Sources, Fate, Effects and Risks, K. Kümmerer, Ed., pp. 3–11, Springer, Berlin, Germany, 2004.
View at: Google Scholar
B. Halling-Sørensen, S. Nors Nielsen, P. F. Lanzky, F. Ingerslev, H. C. Holten-Lützhøft, and S. E. Jørgensen, “Occurrence, fate and effects of pharmaceutical substances in the environment-a review,” Chemosphere, vol. 36, no. 2, pp. 357–393, 1998.
View at: Publisher Site | Google Scholar
P. Spengler, W. Körner, and J. W. Metzger, “Substances with estrogenic activity in effluents of sewage treatment plants in southwestern Germany. 1. Chemical analysis,” Environmental Toxicology and Chemistry, vol. 20, no. 10, pp. 2133–2141, 2001.
View at: Publisher Site | Google Scholar
T. Heberer, “Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data,” Toxicology Letters, vol. 131, no. 1-2, pp. 5–17, 2002.
View at: Publisher Site | Google Scholar
FDA, March 1995, Streamlining food and drug administration-environmental assessments. FDA Backgrounder ${BG}_{95 - 9}$ .
CSTEE (Scientific Committee on Toxicity, Ecotoxicity the Environment), 2001, CPMPpaperRAssessHumPharm12062001.
M. DellaGreca, M. Brigante, and M. Isidori et al., “Phototransformation and ecotoxicity of the drug Naproxen-Na,” Environmental Chemistry Letters, vol. 1, no. 4, pp. 237–241, 2003.
View at: Publisher Site | Google Scholar
J. E. Arrowsmith, S. F. Campbell, and P. E. Cross et al., “Long-acting dihydropyridine calcium antagonists. 1. 2-alkoxymethyl derivatives incorporating basic substituents,” Journal of Medicinal Chemistry, vol. 29, no. 9, pp. 1696–1702, 1986.
View at: Publisher Site | Google Scholar
G. Ragno, A. Garofalo, and C. Vetuschi, “Photodegradation monitoring of amlodipine by derivative spectrophotometry,” Journal of Pharmaceutical and Biomedical Analysis, vol. 27, no. 1-2, pp. 19–24, 2002.
View at: Publisher Site | Google Scholar
D. Dulin and T. Mill, “Development and evaluation of sunlight actinometers,” Environmental Science and Technology, vol. 16, no. 11, pp. 815–820, 1982.
View at: Publisher Site | Google Scholar
OECD (Organization for Economic Cooperation Development), 2000, Environmental Health and Safety Publication.
R. G. Zepp and D. M. Cline, “Rates of direct photolysis in aquatic environment,” Environmental Science and Technology, vol. 11, no. 4, pp. 359–366, 1977.
View at: Publisher Site | Google Scholar
EPA (United States Environmental Protection Agency), “Fate, transport and transformation test guidelines. Direct photolysis rate in water by sunlight,” 1996, OPPTS 835.2210, Washington, DC, USA.
View at: Google Scholar
ASTM (American Society for Testing Materials), “Standard guide for acute toxicity with the rotifer Brachionus,” 1991, E 1440-91, Philadelphia, Pa, USA.
View at: Google Scholar
ISO (International Organization for Standardization), “Water Quality-Determination of the inhibition of the mobility of Daphnia magna Straus (Cladocera, Crustacea)-Acute toxicity test,” 1996, ISO/6341. Geneva, Switzerland.
View at: Google Scholar
ISO (International Organization for Standardization), “Water quality-Determination of chronic toxicity to Ceriodaphnia dubia in 7 days—Population growth inhibition test,” 2001, ISO/CD 20665. Geneva, Switzerland.
View at: Google Scholar
J. Shibuya, M. Nabeshima, H. Nagano, and K. Maeda, “Photochemical reaction of 2,4,4,6-tetrasubstituted 1,4-dihydropyridines in deaerated media: photocolouration and photorearrangement accompanying dehydrogenation,” Journal of the Chemical Society-Perkin Transactions II, no. 8, pp. 1607–1612, 1988.
View at: Publisher Site | Google Scholar
E. Fasani, M. Fagnoni, D. Dondi, and A. Albini, “Intramolecular electron transfer in the photochemistry of some nitrophenyldihydropyridines,” Journal of Organic Chemistry, vol. 71, no. 5, pp. 2037–2045, 2006.
View at: Publisher Site | Google Scholar
R. G. Zepp, J. Holgné, and H. Bader, “Nitrate-induced photooxidation of trace organic chemicals in water,” Environmental Science and Technology, vol. 21, no. 5, pp. 443–450, 1987.
View at: Publisher Site | Google Scholar
R. G. Zepp, P. F. Schlotzhauer, and R. M. Sink, “Photosensitized transformations involving electronic energy transfer in natural waters: role of humic substances,” Environmental Science and Technology, vol. 19, no. 1, pp. 74–81, 1985.
View at: Publisher Site | Google Scholar
C. G. Daughton and T. A. Ternes, “Pharmaceuticals and personal care products in the environment: agents of subtle change?,” Environmental Health Perspectives, vol. 107, supplement 6, pp. 907–938, 1999.
View at: Publisher Site | Google Scholar

Copyright

Copyright © 2007 Marina DellaGreca et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

PDF Download Citation Order printed copies

Views

493

Downloads

1211

Citations