An evaluation of chemical photoreactivity and the relationship to phototoxicity

Regulatory Toxicology and Pharmacology

Volumn 58, Issue 2, 2010, Pages 224-232

  Kleinman, Mark H ^a   Smith, Mark D ^a   Kurali, Edit ^a   Kleinpeter, Sarah ^a   Jiang, Kaina ^a   Zhang, Yongxia ^b   Kennedy Gabb, Sonya A ^a   Lynch, Anthony M ^c   Geddes, Chris D ^d  

^a GLAXOSMITHKLINE   (United States)

^b UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

^c GLAXOSMITHKLINE   (United Kingdom)

^d UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

3T3 NRU; Photodegradation; Photoreactivity; Photosafety testing; Photostability; Phototoxicity; Singlet oxygen; Superoxide anion

Indexed keywords

6 [2 [5 CHLORO 2 (2,4 DIFLUOROBENZYLOXY)PHENYL] 1 CYCLOPENTENYL] 2 PYRIDINECARBOXYLIC ACID; ACRIDINE; AMIODARONE; BERGAPTEN; CARBAMAZEPINE; CETIRIZINE; CHLOROQUINE; CHLORPROMAZINE; CIPROFLOXACIN; CYANOCOBALAMIN; DAPSONE; FLUOROURACIL; FLUTAMIDE; FUROSEMIDE; GLIBENCLAMIDE; GRISEOFULVIN; HYDROCHLOROTHIAZIDE; INDOMETACIN; KETOPROFEN; LEVOFLOXACIN; LOMEFLOXACIN; METYRAPONE; NALIDIXIC ACID; NEUTRAL RED; PIROXICAM; RIBOFLAVIN; SINGLET OXYGEN; SUPEROXIDE; TETRACYCLINE; UNINDEXED DRUG;

ARTICLE; DISCRIMINANT ANALYSIS; DRUG SAFETY; FOOD AND DRUG ADMINISTRATION; IN VITRO STUDY; LIGHT ABSORPTION; PARTIAL LEAST SQUARES REGRESSION; PHOTOCHEMISTRY; PHOTOREACTIVITY; PHOTOSENSITIVITY; PHOTOTOXICITY; PREDICTION; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; QUANTUM YIELD; RISK ASSESSMENT; SCORING SYSTEM; ULTRAVIOLET A RADIATION; ULTRAVIOLET B RADIATION; VALIDATION STUDY;

3T3 CELLS; ALGORITHMS; ANIMALS; DERMATITIS, PHOTOTOXIC; LEAST-SQUARES ANALYSIS; MICE; NEUTRAL RED; PHARMACEUTICAL PREPARATIONS; PHOTOCHEMICAL PROCESSES; PHOTOCHEMISTRY; PRINCIPAL COMPONENT ANALYSIS; SINGLET OXYGEN; SUPEROXIDES; TOXICITY TESTS; ULTRAVIOLET RAYS;

EID: 77957344807     PISSN: 02732300     EISSN: 10960295     Source Type: Journal    
DOI: 10.1016/j.yrtph.2010.06.013     Document Type: Article

References (40)

1. Albini A., Fasani E. Rationalizing the Photochemistry of Drugs 2004, 67-110. CRC Press, Boca Raton. H.H. Tonnesesen (Ed.).
2. Allen J.M., et al. Photochemical formation of singlet molecular oxygen in illuminated aqueous solutions of several commercially available sunscreen active ingredients. Chem. Res. Toxicol. 1996, 9:605-609.
3. Anderson N.H. Photostability testing: design and interpretation of tests on drug substances and dosage forms. Photostab. Drugs Drug Formulations [Int. Meet. Photostab. Drugs] 1996, 1:305-321.
4. Atlas Material Testing Solutions. 2006. Conforming to the ICH guideline for the photostability testing of new drug substances and drug products (ICH Q1B) using the Atlas SUNTEST CPS/CPS+ and XLS/XLS+. Atlas Material Testing Technology LLC, 1.01.06.
5. Balls M., et al. The three Rs: the way forward: the report and recommendations of ECVAM Workshop 11. Altern. Lab. Anim. 1995, 23:838-866.
6. Baughman B.M., et al. Structural and spectroscopic studies of the photophysical properties of benzophenone derivatives. J. Phys. Chem. A 2009, 113:8011-8019.
7. Deleo V.A. Photocontact dermatitis. Dermatol. Ther. 2004, 17:279-288.
8. Diffey B.L. Sources and measurement of ultraviolet radiation. Methods 2002, 28:4-13.
9. EMEA Committee for Proprietary Medicinal Products (CPMP), 2002. Note for guidance on photosafety testing (CPMP/SWP/398/01. http://www.ema.europa.eu/pdfs/human/swp/039801en.pdf.
10. Epstein J.H. Phototoxicity and photoallergy in man. J. Am. Acad. Dermatol. 1983, 8:141-147.
11. Eriksson L., et al. Multi and Megavariate Data Analysis: Principles and Applications 2001, Umetrics Academy, Umea Sweden.
12. FDA, 2003. FDA Guidance for industry - Guidance on photosafety testing. http://www.fda.gov/downloads/drugs/guidancecomplianceregulatoryinformation/guidances/ucm079252.pdf.
13. Ferguson J. Photosensitivity due to drugs. Photodermatol. Photoimmunol. Photomed. 2002, 18:262-269.
14. Gocke E., et al. Considerations on photochemical genotoxicity: report of the international workshop on genotoxicity test procedures working group. Environ. Mol. Mutagen. 2000, 35:173-184.
15. Hazardous Substances Data Bank [Internet] (2009). Bethesda (MD): National Library of Medicine (US). Available from: <> (accessed 2009). http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB.
16. Henry B., et al. Can light absorption and photostability data be used to assess the photosafety risks in patients for a new drug molecule? J. Photochem. Photobiol. B Biol. 2009, 96:57-62.
17. Holzhutter H.G. A general measure of in vitro phototoxicity derived from pairs of dose response curves and it's use for predicting the in vitro phototoxicity of chemicals. Altern. Lab. Anim. 1997, 25:445-462.
18. ICH, 1996. ICH stability testing: photostability testing of new drug substances and products Q1B. http://www.ich.org/cache/compo/363-272-1.html.
19. ISO, 1999. ISO/CIE 17166:1999 Erythema reference action spectrum and standard erythema dose pp 1-4. http://www.iso.org/iso/catalogue_detail.htm?csnumber=31245.
20. Johnson B.E., Ferguson J. Drug and chemical photosensitivity. Semin. Dermatol. 1990, 9:39-46.
21. Jones P.A., King A.V. High throughput screening (HTS) for phototoxicity hazard using the in vitro 3T3 neutral red uptake assay. Toxicol. Vitro 2003, 17:703-708.
22. Lowry T.H., Richardson K.S. Mechanism and Theory in Organic Chemistry 1987, Harper & Row, New York.
23. Lynch, A. M., Wilcox, P, (2010). Review of the performance of the 3T3 NRU in vitro phototoxicity assay in the pharmaceutical industry. Exp. Toxicol. Pathol. doi:10.1016/j.etp.2009.12.001.
24. Micromedex® Healthcare Series, 2009. [intranet database]. Version 5.1. Greenwood Village, Colo: Thomson Reuters (Healthcare) Inc.
25. Molecular Probes Inc. 2010. Singlet oxygen sensor green reagent. (accessed 27.04.10). http://probes.invitrogen.com/media/pis/mp36002.pdf?id=mp36002.
26. Moore D.E. Drug-induced cutaneous photosensitivity: incidence, mechanism, prevention and management. Drug Saf. 2002, 25:345-372.
27. Neumann N.J., et al. Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods. J. Photochem. Photobiol. B Biol. 2005, 79:25-34.
28. OECD, 2004. OECD/OCDE 432: OECD guideline for the testing of chemicals. In vitro 3T3 NRU phototoxicity test. http://www.oecdbookshop.org.
29. Onoue S., Tsuda Y. Analytical studies on the prediction of photosensitive/phototoxic potential of pharmaceutical substances. Pharm. Res. 2006, 23:156-164.
30. Parisi A.V., Wong J.C.F. Erythemal irradiances of filtered ultraviolet radiation. Phys. Med. Biol. 1997, 42:1263-1275.
31. 2 and O2-·) by psoralens and ultraviolet radiation (320-400nm). Biochim. Biophys. Acta 1984, 798:115-126.
32. Qunitero B., Miranda M.A. Mechanisms of photosensitization induced by drugs: A general survey. Ars Pharmaceutica 2000, 41(1):27-46.
33. 2 (1Δg) sensitization. J. Photochem. Photobiol., A 1994, 79:11-17.
34. Spielmann H., et al. EEC/COLIPA project on in vitro phototoxicity testing: first results obtained with a Balb/c 3T3 cell phototoxicity assay. Toxicol. Vitro 1994, 8:793-796.
35. Spielmann H., et al. In Vitro photoxicity testing: the report and recommendations of ECVAM Workshop 2. Altern. Lab. Anim. 1994, 22:314-348.
36. Spielmann H., et al. The international EU/COLIPA in vitro phototoxicity validation study: results of phase II (blind trial). Part 1: the 3T3 NRU phototoxicity test. Toxicol. Vitro 1998, 12:305-327.
37. Spielmann H., et al. The second ECVAM workshop on phototoxicity testing: the report and recommendations of ECVAM workshop 42. Altern. Lab. Anim. 2000, 28:777-814.
38. Tardivo J.P., et al. Methylene blue in photodynamic therapy: from basic mechanisms to clinical applications. Photodiagn. Photodyn. Ther. 2005, 2:175-191.
39. Veber D.F., et al. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45:2615-2623.
40. Williams A.T.R., et al. Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer. Analyst 1983, 108:1067-1071.