ArticleThe British journal of dermatology2015
Voriconazole N-oxide and its ultraviolet B photoproduct sensitize keratinocytes to ultraviolet A.
Article in The British journal of dermatology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 61 citations in OpenAlex.
- Microdialysis of Voriconazole and its N-Oxide Metabolite: Amalgamating Knowledge of Distribution and Metabolism Processes in Humans.Pharmaceutical research · 2022Trial
- Photochemistry of Aromatic N-Oxides in Water Probed by Time-Resolved X-ray Absorption Spectroscopy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Epidemiology and Treatment Outcomes of Voriconazole-Induced Invasive Cutaneous Squamous Cell Carcinoma in Japanese Patients with Pulmonary Aspergillosis.Journal of plastic and reconstructive surgery · 2026Article
- Skin Cancer in Solid Organ Transplant Recipients: A Review.American journal of clinical dermatology · 2026Review
- Pharmacogenetics of steady-state metabolism, pharmacokinetics, and adverse effects of voriconazole in healthy participants.Drug metabolism and disposition: the biological fate of chemicals · 2025Article
- Voriconazole metabolism is associated with the number of skin cancers per patient.Archives of dermatological research · 2024Article
- Voriconazole Metabolism is Associated with the Number of Skin Cancers Per Patient.Research square · 2024Article
- The phenomenon of phototoxicity and long-term risks of commonly prescribed and structurally diverse drugs.Journal of photochemistry and photobiology · 2024Article
- Electrochemical Simulation of Phase I Hepatic Metabolism of Voriconazole Using a Screen-Printed Iron(II) Phthalocyanine Electrode.Pharmaceutics · 2023Article
- Dermatologic complications in transplantation and cellular therapy for acute leukemia.Best practice & research. Clinical haematology · 2023Review
- Microdialysis of Drug and Drug Metabolite: a Comprehensive In Vitro Analysis for Voriconazole and Voriconazole N-oxide.Pharmaceutical research · 2022Article
- Aggressive Cutaneous Squamous Cell Carcinomas Following Treatment for Graft-versus-Host Disease: A Case Report and Review of Risk Factors.Dermatopathology (Basel, Switzerland) · 2022Article
- Towards the Elucidation of the Pharmacokinetics of Voriconazole: A Quantitative Characterization of Its Metabolism.Pharmaceutics · 2022Article
- A review on association of fungi with the development and progression of carcinogenesis in the human body.Current research in microbial sciences · 2022Review
- Drug-Induced Photosensitivity-From Light and Chemistry to Biological Reactions and Clinical Symptoms.Pharmaceuticals (Basel, Switzerland) · 2021Review
- Review
- Review of Pharmacologic Considerations in the Use of Azole Antifungals in Lung Transplant Recipients.Journal of fungi (Basel, Switzerland) · 2021Review
- The incidence of cutaneous squamous cell carcinoma in patients receiving voriconazole therapy for chronic pulmonary aspergillosis.Naunyn-Schmiedeberg's archives of pharmacology · 2020Article
- Voriconazole-Induced Squamous Cell Carcinoma after Hematopoietic Stem Cell Transplantation Showing Early-Stage Vascular Invasion.Dermatopathology (Basel, Switzerland) · 2020Article
- Cutaneous squamous cell carcinoma in the organ transplant recipient.Oral oncology · 2020Review
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
backgroundThe antifungal agent, voriconazole, is associated with phototoxicity and photocarcinogenicity. Prior work has indicated that voriconazole and its hepatic N-oxide metabolite do not sensitize keratinocytes to ultraviolet B (UVB). Clinical observations have suggested that ultraviolet A (UVA) may be involved.
objectivesTo determine the photochemistry and photobiology of voriconazole and its major hepatic metabolite, voriconazole N-oxide. MATERIALS AND
methodsVoriconazole and voriconazole N-oxide were spectrophotometrically monitored following various doses of UVB. Cultured human keratinocytes were treated with parental drugs or with their UVB photoproducts, and survival following UVA irradiation was measured by thiazolyl blue metabolism. Reactive oxygen species (ROS) and 8-oxoguanine were monitored by fluorescence microscopy.
resultsVoriconazole and voriconazole N-oxide have varying UVB absorption but do not acutely sensitize cultured human keratinocytes following UVB exposure. However, sustained UVB exposures produced notable dose- and solvent-dependent changes in the absorption spectra of voriconazole N-oxide, which in aqueous solution acquires a prominent UVA absorption band, suggesting formation of a discrete photoproduct. Neither the parental drugs nor their photoproducts sensitized cells to UVB although all but voriconazole N-oxide were moderately toxic to cells in the dark. Notably, both voriconazole N-oxide and its UVB photoproduct, but not voriconazole or its photoproduct, additionally sensitized cells to UVA by greater than three-fold relative to controls in association with UVA-induced ROS and 8-oxoguanine levels.
conclusionsVoriconazole N-oxide and its UVB-photoproduct act as UVA-sensitizers that generate ROS and that produce oxidative DNA damage. These results suggest a mechanism for the phototoxicity and photocarcinogenicity observed with voriconazole treatment.
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