Skip to main content

Phototoxic effects of N-oxidized drugs and related compounds

  • Chapter
N-Oxidation of Drugs

Abstract

N-Oxidized compounds find extensive application as constituents of drugs, cosmetics, food and agricultural chemicals. Although very useful and almost indispensible, they can also produce adverse biological effects. These toxic (side-) effects include genotoxicity (carcinogenicity), but also immune diseases, such as allergy. Enzymatic activation of N-oxidized compounds as inducers of such processes has received much attention. It is assumed that reactive intermediates or instable products formed during (minor) metabolic processes damage biomacromolecules in the genetic or immune system.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Bakri, A., Beijersbergen van Henegouwen, G.M.J, and Chanal, J.L. (1983) Photopharmacology of the tranquilizer chlordiazepoxide in relation to its phototoxicity. Photochem .Photobiol., 38, 177–83.

    Article  PubMed  CAS  Google Scholar 

  • Bakri, A., Beijersbergen van Henegouwen, G.M.J, and Chanal, J.L. (1985) Involvement of the N4-oxide group in the phototoxicity of chlordiazepoxide in the rat. Photodermatology, 2, 205–12.

    PubMed  CAS  Google Scholar 

  • Bakri, A., Beijersbergen van Henegouwen, G.M.J, and De Vries, H. (1988) Photobinding of some 7-chloro-l,4-benzodiazepines to human plasma protein in vitro and photopharmacology of diazepam in the rat. Pharm. Weekbl. (Sci), 10, 122–9.

    Article  CAS  Google Scholar 

  • Barrett, M.D. and Brown, K.R. (1985) Photochemical binding of photoallergens to human serum albumin: a simple in vitro method for screening potential photoallergens. Toxicol. Lett., 24, 1–6.

    Article  Google Scholar 

  • Beijersbergen van Henegouwen, G.M.J. (1988) In vitro and in vivo research on phototoxic xenobiotics: structure-reactivity relationships. Arch. Toxicol. Suppl., 12, 3–9.

    Article  CAS  Google Scholar 

  • Beijersbergen van Henegouwen, G.M.J., Wijn, E.T. and Schoonderwoerd, S.A. (1989) A method for the determination of PUVA-induced in vivo irreversible binding of 8-methoxypsoralen (8-MOP) to epidermal lipids, proteins and DNA/RNA. J. Photochem. Photobiol., B: Biol., 4, 631–5.

    Article  Google Scholar 

  • Black, H.S. (1987) Potential involvement of free radical reactions in ultraviolet light-mediated cutaneous damage. Photochem. Photobiol., 46, 213–21.

    Article  PubMed  CAS  Google Scholar 

  • Busker, R.W. (1989) The formation of antibodies against photoadducts between nitrofurantoin and plasma proteins in rabbits, in Photoreactivity of Nitrofurantoin as a Possible Cause of Some of its Side-effects, Ph.D.-thesis, Leiden University, Ch. 7, pp. 78–86.

    Google Scholar 

  • Busker, R.W. and Beijersbergen van Henegouwen, G.M.J. (1987) The photolysis of nitrofurantoin and of 5-nitrofurfural in aqueous solutions: nucleophilic substitution of the nitro group. Photochem. Photobiol., 45, 331–5.

    Article  CAS  Google Scholar 

  • Busker, R.W., Beijersbergen van Henegouwen, G.M.J., Menke, R.F. and Vasbinder, G. (1988a) Formation of methemoglobin by photoactivation of nitrofurantoin and of 5-nitrofurfural in rats exposed to UVA light. Toxicology, 51, 255–6.

    Article  PubMed  CAS  Google Scholar 

  • Busker, R.W., Beijersbergen van Henegouwen, G.M.J., Van Ballegooie, E.P. and Vasbinder, G. (1988b) Irreversible binding of nitrofurantoin to skin and to plasma proteins of UVA exposed rats. Photochem. Photobiol., 48, 683–8.

    Article  PubMed  CAS  Google Scholar 

  • Busker, R.W., Beijersbergen van Henegouwen, G.M.J., Vaasen, A.J.H. and Menke, R.F. (1989) Irreversible photobinding of nitrofurantoin and of nitrofurfural to plasma protein in vitro. J. Photochem. Photobiol. B: Biol., 4, 207–19.

    Article  CAS  Google Scholar 

  • Campbell, K.P., Lipshutz, G.M. and Denney, G.H. (1984) Direct photoaffinity labeling of the high affinity nitrendipine-binding site in subcellular membrane fractions isolated from canine myocardium. J. Biol. Chem., 259, 5384–7.

    PubMed  CAS  Google Scholar 

  • Cornelissen, P.J.G., Beijersbergen van Henegouwen, G.M.J, and Mohn, G.R. (1980) Structure and photobiological activity of 7-chloro-l,4-benzodiazepines. Studies on the phototoxic effects of chlordiazepoxide, desmethylchlordiazepoxide and demoxepam using a bacterial indicator system. Photochem. Photobiol., 32, 653–61.

    Article  PubMed  CAS  Google Scholar 

  • Dall’Acqua, F. and Rodighiero, G. (1984) Biological and medicinal aspects of furocoumarins (psoralens and angelicins), in Primary Photo-processes in Biology and Medicine (eds R.V. Bensasson, G. Jori, E.J. Land and T.G. Truscott), NATO ASI Series Life Sciences, Plenum, New York, vol. 85, pp. 277–94.

    Google Scholar 

  • De Mol, N.J. and Beijersbergen van Henegouwen, G.M.J. (1981) Relation between some photobiological properties of furocoumarins and their extent of singlet oxygen production. Photochem. Photobiol., 33, 815–19.

    Article  PubMed  Google Scholar 

  • De Vries, H., Beijersbergen van Henegouwen, G.M.J, and Wouters, R. (1983) Correlation between phototoxicity of some 7-chloro-l,4-benzodiazepines and their (photo)chemical properties. Pharm. Weekbl. (Sci), 5, 302–8.

    Article  Google Scholar 

  • De Vries, H., Beijersbergen van Henegouwen, G.M.J, and Huf, F.A. (1984) Photochemical decomposition of chloramphenicol in a 0.25% eye drop and in a therapeutic intraocular concentration. Int. J. Pharm., 20, 265–71.

    Article  Google Scholar 

  • De Vries, H., Beijersbergen van Henegouwen, G.M.J., Kalloe, F. and Berkhuysen, M.H.J. (1990) Phototoxicity of olaquindox in the rat. Res. Vet. Sci., 48, 240–4.

    PubMed  Google Scholar 

  • De Vries, H., Bojarski, J., Donker, A.A., Bakri, A. and Beijersbergen van Henegouwen, G.M.J. (1990a) Photochemical reactions of quindoxin, olaquindox, carbadox and cyadox with oritein, indicating photoallergic properties. Toxicology, 63, 85–95.

    Article  PubMed  Google Scholar 

  • Eyer, P., Lierheimer, E. and Schneller, M. (1984) Reactions of nitroschlor-amphenicol in blood. Biochem. Pharmacol., 33, 2299–308.

    Article  PubMed  CAS  Google Scholar 

  • Ford, R.A. (1984) Photoallergenicity testing of fragrance material. A review on photoallergy by musk ambrette in male human patients. Nippon Koshohin Kagakkaishi, 8, 301–4.

    CAS  Google Scholar 

  • Francalanci, S., Gola, M., Giorgini, S. et al (1986) Occupational photocontact dermatitis from Olaquindox. Contact Dermatitis, 15, 112–14.

    Article  PubMed  CAS  Google Scholar 

  • Gross, B.J., Blanchflower, R.V., Burke, T.R. et al. (1982) Bone marrow toxicity in vitro of chloramphenicol and its metabolites. Toxicol. Appl. Pharmacol., 64, 557–65.

    Article  PubMed  CAS  Google Scholar 

  • Holick, M.F. (1985) The photobiology of vitamin D and its consequences for humans, in The Medical and Biological Effects of Light (eds R.J. Wurtman, M.J. Baum and J.T. Potts Jr.), Ann. N. Y. Acad. Sci .453, 1–13.

    Google Scholar 

  • Ichida, S., Fujisue, T. and Masada, A. (1989a) Characteristics of specific binding of nitrendipine and PN 200–110 to various crude membranes: induction of irreversible binding by UV irradiation. J. Biochem. (Tokyo), 105, 760–6.

    PubMed  CAS  Google Scholar 

  • Ichida, S., Fujisue, T. and Masada, A. (1989b) Photoaffinity labeling with dihydropyridine derivatives of crude membranes from rat skeletal, cardiac, ileal and uterine muscles and whole brain. J. Biochem. (Tokyo), 105, 767–75.

    PubMed  CAS  Google Scholar 

  • McDonagh, A.F. (1985) Light effects on transport and excretion of bilirubin in newborns, in The Medical and Biological Effects of Light (eds R.J. Wurtman, M.J. Baum and J.T. Potts Jr.), Ann. N. Y. Acad. Sci .453, 65–72.

    Google Scholar 

  • Morison, W.L., McAuliffe, D.J., Parrish, J.A. and Bloch, K.J. (1982) In vitro assay for phototoxic chemicals. J. Invest. Dermatol., 78, 460–3.

    Article  PubMed  CAS  Google Scholar 

  • Motten, A.G., Chignell, C.F. and Mason, R.P. (1983) Spectroscopic studies of cutaneous photosensitizing agents - VI. Identification of the free radicals generated during the photolysis of musk ambrette, musk xylene and musk ketone. Photochem. Photobiol., 38, 671–8.

    Article  CAS  Google Scholar 

  • Parker, R.D., Buehler, E.V. and Newmann, E.A. (1986) Phototoxicity, photoallergy and contact photosensitization of nitro musk perfume raw materials. Contact Dermatitis, 14, 103–9.

    Article  PubMed  CAS  Google Scholar 

  • Pöhlmann, H., Theil, F.-P., Franke, P. and Pfeifer, S. (1986) In vitro- und in vivo-Untersuchungen zur fotochemischen Reaktivitat von Methaqualon-1-oxid. Pharmazie, 41, 856–8.

    PubMed  Google Scholar 

  • Schoonderwoerd, S.A. and Beijersbergen van Henegouwen, G.M.J. (1987) Irreversible photobinding to skin constituents after systemic administration of chlorpromazine to Wistar rats. Photochem. Photobiol., 46, 501–5.

    Article  PubMed  CAS  Google Scholar 

  • Schoonderwoerd, S.A., Beijersbergen van Henegouwen, G.M.J, and Luijendijk, J.J. (1988) Photobinding of chlorpromazine and its sulfoxide in vitro and in vivo. Photochem. Photobiol., 48, 621–7.

    Article  PubMed  CAS  Google Scholar 

  • Schoonderwoerd, S.A., Beijersbergen van Henegouwen, G.M.J, and Van Belkum, S. (1989) In vivo photodegradation of chlorpromazine. Photochem. Photobiol., 50, 659–64.

    Article  PubMed  CAS  Google Scholar 

  • Thoma, K. and Klimek, R. (1985a) Untersuchungen zur Photostabilität von Nifedipin, 1. Mitt.: Zersetzungskinetik und Reaktionsmechanismus. Pharm. Ind., 47, 207–15.

    CAS  Google Scholar 

  • Thoma, K. and Klimek, R. (1985b) Untersuchungen zur Photostabilitat von Nifedipin, 2. Mitt.: Einflusz von Milieubedingungen. Pharm. Ind., 47, 319–27.

    CAS  Google Scholar 

  • Thomas, S.E. and Wood, M.L. (1986) Photosensitivity reactions associated with nifedipine. Br. Med. J., 292, 992.

    Article  Google Scholar 

  • Yunis, A.A., Miller, A.M., Salem, Z. et al. (1980) Nitrosochloramphenicol: possible mediator in chloramphenicol-induced aplastic anemia. J. Lab. Clin. Med.,96, 36–46.

    PubMed  CAS  Google Scholar 

  • Zaynoun, S., Johnson, B.E. and Frain-Bell, W. (1976) The investigation of Quindoxin photosensitivity. Contact Dermatitis, 2, 343–52.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Beijersbergen van Henegouwen, G.M.J. (1991). Phototoxic effects of N-oxidized drugs and related compounds. In: Hlavica, P., Damani, L.A. (eds) N-Oxidation of Drugs. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3112-4_26

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-3112-4_26

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5378-5

  • Online ISBN: 978-94-011-3112-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics