title: The chlorination behaviour and environmental fate of the antiretroviral drug nevirapine in South African surface water.
abstract: The wastewater treatment process, besides discharging pharmaceuticals into the environment, has been found to result in the formation of a variety of undescribed compounds. Here we investigate the laboratory scale chlorination of the commonly used anti-HIV drug Nevirapine, characterise its disinfection transformation products (DTPs), and using liquid chromatography with high resolution mass spectrometry, screen environmental surface water for these DTPs. Chlorination of Nevirapine was scaled up, fractioned by preparative chromatography and the fractions were tested in vitro for toxicity and anti-HIV activity. Nevirapine was found to be resistant to degradation at relevant chlorination levels, which may partially explain its ubiquitous presence in South African surface water. During simulated chlorination, a variety of DTPs with varying properties were formed, some of which were detected in the environment, close to wastewater treatment plants. Interestingly, some of these compounds, although not as toxic as Nevirapine, retained antiviral activity. Further purification and synthesis is required to fully characterise these novel molecules.
authors: Protechnik Laboratories, A Division of ARMSCOR SOC Ltd, 103 Combretum Crescent, Centurion, Pretoria, 0001, South Africa; Department of Chemistry, University of Pretoria, Lynwood Road, Pretoria, 0001, South Africa. Electronic address: timw@protechnik.co.za.
authors: Timothy Paul
authors: TP
authors: Wood
authors: Centre for HIV and STI: HIV Virology Section (Morris Laboratory), National Institute for Communicable Diseases (NICD), A Division of the National Health Laboratory Service (NHLS), 1 Modderfontein Road, Sandringham, 2131, South Africa. Electronic address: adriaanb@nicd.ac.za.
authors: Adriaan Erasmus
authors: AE
authors: Basson
authors: Department of Internal Medicine, 1 Military Hospital, South African Military Health Services, Voortrekker Street, Pretoria, 0001, South Africa. Electronic address: corneliaduv@mtnloaded.co.za.
authors: Cornelia
authors: C
authors: Duvenage
authors: Department of Chemistry, University of Pretoria, Lynwood Road, Pretoria, 0001, South Africa. Electronic address: egmont.rohwer@up.ac.za.
authors: Egmont Richard
authors: ER
authors: Rohwer
mesh_terms: D054879:Halogenation; D019829:Nevirapine; D053719:Tandem Mass Spectrometry; D014867:Water / Q000737:chemistry*; D014874:Water Pollutants, Chemical / Q000737:chemistry; D018508:Water Purification
chemical_list: D014874:Water Pollutants, Chemical; D014867:Water; D019829:Nevirapine
keywords: Chlorination; LC-MS; LC-QTOF; Nevirapine; Surface water; Wastewater