the most minor. Chemistry Reboxetine has two chiral centers. Thus, four stereoisomers may exist, the (R,R)-, (S,S)-, (R,S)-, and (S,R)-isomers. The active ingredient of reboxetine is a racemic mixture of two enantiomers, the (R,R)-(–)- and (S,S)-(+)-isomer. History Reboxetine was discovered at Farmitalia-Carlo Erba and was first published in 1984; Farmitalia did the first clinical studies. Farmitalia was acquired by Pharmacia in 1993, and Pharmacia in turn was acquired by Pfizer in 2003. It was first approved in Europe in 1997 and was provisionally approved by the FDA in 1999. In 2001 the FDA issued Pfizer a "not approvable" letter based on clinical trials the FDA had required when it issued the preliminary approval letter. In 2010, the German Institute for Quality and Efficiency in Health Care (IQEHC) published results of a meta-analysis of clinical trial data for reboxetine in acute depression, which included data on about 3,000 subjects that Pfizer had never published but had mentioned; IQEHC had combed through Pfizer's publications and reboxetine approvals and had determined this data was missing from the publication record. The analysis of the complete data set yielded a result that reboxetine was not more effective than placebo but had more side effects than placebo and more than fluoxetine; the paper led to widespread and sharp criticism of Pfizer, and stronger calls for publication of all clinical trial data. Society and culture Brand names Edronax is the brand name of reboxetine in every English-speaking country that has approved it for clinical use. Brand names include (where † denotes a product that is no longer marketed): Davedax (IT) Edronax (AU, AT, BE, CZ, DK, FI, DE, IE, IL, IT, MX, NZ, NO, PH, PL, PT, ZA, SE, CH, TH, TR, UK) Irenor (ES) Norebox (ES) Prolift (AR,† BR, CL, VE†) Solvex (DE) Yeluoshu (CN) Zuolexin (CN) References External links Reboxetine: A Novel Antidepressant Antidepressants Morpholines Nicotinic antagonists Pfizer brands Norepinephrine reuptake inhibitors Phenol ethers Potassium channel blockers Italian inventions