Drug repositioning aims to reuse “old” drugs to treat diseases outside their approved indication(s). Composition-of-matter patents and FDA exclusivities can hinder the immediate availability of some drugs to be repositioned (repurposed). Here, we analyze data from the FDA Orange Book and use current on-market patent validity and exclusivities to classify drugs into on-patent (ONP), off-patent (OFP), and off-market (OFM) sets. In the absence of an unanimously accepted definition for small molecules, these sets include organic molecules and peptides with molecular weight between 100 and 1250, which resulted in 237 ONP drugs, 320 OFM, and 996 OFP drugs, respectively. We discuss the differences between the three categories in terms of primary molecular properties, chemical diversity, mechanism-of-action target classes, and therapeutic areas and comment on the enrichment of OFP drugs in the near future. Given the intellectual property landscape, and in the absence of specific property rights, we suggest that drugs should be prioritized as follows, to improve the repositioning strategy: (i) OFP, (ii) OFM, and (iii) ONP, respectively.