Crystal structure of pirfenidone (5-methyl-1-phenyl-1H-pyridin-2-one): an active pharmaceutical ingredient (API)

• Main Authors: Mauro Barbero, Matteo Mossotti, Angelo Sironi, Giovanni Battista Giovenzana, Valentina Colombo
• Format: Article
• Language: English
• Published: International Union of Crystallography 2019-07-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; pirfenidone; active pharmaceutical ingredient (API); idiopathic pulmonary fibrosis (IPF); hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989019006418

The crystal structure of pirfenidone, C12H11NO [alternative name: 5-methyl-1-phenylpyridin-2(1H)-one], an active pharmaceutical ingredient (API) approved in Europe and Japan for the treatment of Idiopathic pulmonary fibrosis (IPF), is reported here for the first time. It was crystallized from toluene by the temperature gradient technique, and crystallizes in the chiral monoclinic space group P21. The phenyl and pyridone rings are inclined to each other by 50.30 (11)°. In the crystal, molecules are linked by C–H...O hydrogen bonds involving the same acceptor atom, forming undulating layers lying parallel to the ab plane.