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Herein we report the application of a rational target\u2010based drug\u2010repurposing approach to find diverse applications for our in\u2010house collection of compounds. The carbonic anhydrase (CA, EC\u20054.2.1.1) metalloenzyme superfamily was identified as a potential target of our compounds. The combination of a thoroughly validated docking screening protocol, together with in\u2005vitro assays against various CA families and isoforms, allowed us to identify two unprecedented chemotypes as CA inhibitors. 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