10251. Pirfenidone

Nomenclature

CAS number: 53179-13-8
5-Methyl-1-phenyl-2(1H)-pyridinone; AMR-69; Deskar (Marnac).
C12H11NO; mol wt 185.22.
C 77.81%, H 5.99%, N 7.56%, O 8.64%.

Description and references

Anti-inflammatory and antifibrotic agent. Prepd by phenylation of 5-methyl-2-pyridinone: S. M. Gadekar, US 3839346 (1974 to Affiliated Med. Res.); by photochemical rearrangement of N-phenyl-6-methylpyridinium-3-olate: T. Laerum, K. Undheim, Acta Chem. Scand. B 32, 68 (1978) DOI. HPLC determn in plasma: Y. Wang et al., Biomed. Chromatogr. 20, 1375 (2006) DOI PubMed. Clinical pharmacokinetics: S. Shi et al., J. Clin. Pharmacol. 47, 1268 (2007) DOI PubMed. Clinical trial in idiopathic pulmonary fibrosis: A. Azuma et al., Am. J. Respir. Crit. Care Med. 171, 1040 (2005) DOI PubMed. Review: S. A. Antoniu, Expert Opin. Invest. Drugs 15, 823-828 (2006) DOI PubMed.

Chemical structure

Properties

White solid from hot water, mp 102-104° (Gadekar); also reported as mp 103-105° from benzene-light petroleum (Laerum, Undheim). Sol in methanol.

Therapeutic Category

Antifibrotic; in treatment of idiopathic pulmonary fibrosis.

Keywords

Antifibrotic