Nitrile - Occurrence and Applications

Occurrence and Applications

Nitriles occur naturally in a diverse set of plant and animal sources. Over 120 naturally occurring nitriles have been isolated from terrestrial and marine sources. Nitriles are commonly encountered in fruit pits, especially almonds, and during cooking of Brassica crops (such as cabbage, brussel sprouts, and cauliflower), which release nitriles being released through hydrolysis. Mandelonitrile, a cyanohydrin produced by ingesting almonds or some fruit pits, releases hydrogen cyanide and is responsible for the toxicity of cyanogenic glycosides.

Over 30 nitrile-containing pharmaceuticals are currently marketed for a diverse variety of medicinal indications with more than 20 additional nitrile-containing leads in clinical development. The nitrile group is quite robust and, in most cases, is not readily metabolized but passes through the body unchanged. The types of pharmaceuticals containing nitriles is diverse, from Vildagliptin an antidiabetic drug to Anastrazole which is the gold standard in treating breast cancer. In many instances the nitrile mimics functionality present in substrates for enzymes, whereas in other cases the nitrile increases water solubility or decreases susceptibility to oxidative metabolism in the liver.The nitrile functional group is found in several drugs.

• Structure of periciazine, an antipsychotic studied in the treatment of opiate dependence.

• Structure of citalopram, an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class.

• Structure of cyamemazine, an antipsychotic drug.

• Structure of fadrozole, an aromatase inhibitor for the treatment of breast cancer.

• Structure of letrozole, an oral non-steroidal aromatase inhibitor for the treatment of certain breast cancers.