Aptiganel (Cerestat; CNS-1102) is an unsuccessful drug candidate which acts as a noncompetitive NMDA antagonist, and that was under development by Cambridge Neuroscience, Inc as a treatment for stroke due to its neuroprotective effects. However, despite positive results in animal studies, human trials showed limited efficacy and undesirable side effects such as sedation and hallucinations, leading to the discontinuation of clinical development.
Chemistry
Synthesis
1-Naphthylamine is reacted with cyanogen bromide to give 2. Treatment of this intermediate with 3-ethyl-N-methylaniline leads to addition to the cyano group and formation of the corresponding diaryl guanidine, aptiganel, 3.
History The drug's failure led to the collapse of Cambridge Neuroscience in 1998Staff, Boston Business Journal. May 7, 1998. CNSI appoints new president, CEO and its eventual sale to CeNeS Pharmaceuticals in 2000.Staff, ICIS. 23 May 2000 CeNeS to buy US neuroscience firm CNSI for $44m
See also Ditolylguanidine CNS-1237 (shares most of the same structural entities) CNS-5161
References