Esbriet

Pirfenidone

Clinical data
Trade names	Esbriet, Pirespa, Etuary
AHFS/Drugs.com	International Drug Names
License data	EU EMA: by INN
Routes of administration	Oral
ATC code	L04AX05 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Protein binding	50–58%
Metabolism	Hepatic (70–80% CYP1A2-mediated; minor contributions from CYP2C9, CYP2C19, CYP2D6 and CYP2E1)
Biological half-life	2.4 hours
Excretion	Urine (80%)
Identifiers
IUPAC name 5-Methyl-1-phenylpyridin-2-one
CAS Number	53179-13-8
PubChem CID	40632
ChemSpider	37115
UNII	D7NLD2JX7U
KEGG	D01583 Y
ChEBI	CHEBI:32016 Y
ChEMBL	CHEMBL1256391 N
ECHA InfoCard	100.150.129
Chemical and physical data
Formula	C12H11NO
Molar mass	185.22 g/mol
3D model (JSmol)	Interactive image
Solubility in water	10 mg/mL at 60 °C mg/mL (20 °C)
SMILES CC1=CN(C(=O)C=C1)C2=CC=CC=C2
InChI InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3 Key:ISWRGOKTTBVCFA-UHFFFAOYSA-N
NY (what is this?)

Pirfenidone is a medication used for the treatment of idiopathic pulmonary fibrosis (IPF). It works by reducing lung fibrosis through downregulation of the production of growth factors and procollagens I and II.

It was developed by several companies worldwide, including the original patent holder, Marnac, InterMune Inc. (now part of Roche), Shionogi Ltd., and GNI Group Ltd. In 2008, it was first approved in Japan for the treatment of IPF after clinical trials, under the trade name of Pirespa by Shionogi. In October 2010, the Indian Company Cipla launched it as Pirfenex. In 2011, it was approved for use in Europe for IPF under the trade name Esbriet; it was approved in Canada in 2012 under the trade name Esbriet; and was approved in the United States in October 2014 under the same name. In September 2011, the Chinese State Food and Drug Administration provided GNI Group Ltd with new drug approval of pirfenidone in China, and later manufacture approval in 2013 under the trade name of Etuary.

In 2014 it was approved in Mexico under the name KitosCell LP, indicated for pulmonary fibrosis and liver fibrosis. There is also a topical form created for the treatment of abnormal wound healing processes.

In Europe, pirfenidone is indicated for the treatment of mild-to-moderate idiopathic pulmonary fibrosis. It was approved by the European Medicines Agency (EMA) in 2011. In October 2008, it was approved for use in Japan, in India in 2010, and in China in 2011 (commercial launch in 2014). In October 2014, it was approved for sale in the United States.

In Mexico it has been approved on a gel form for the treatment of scars and fibrotic tissue and has proven to be effective in the treatment of skin ulcers

Pirfenidone is frequently associated with gastrointestinal side effects such as dyspepsia, nausea, gastritis, gastroesophageal reflux disease (GERD) and vomiting.To reduce the severity of these reactions, pirfenidone is to be taken after meals.

Pirfenidone is known to cause photosensitivity reactions, rash, pruritus and dry skin. Patients are usually advised to avoid direct exposure to sunlight, including sun lamps, and to use protective clothing and sunscreening agents. Continuing photosensitivity reactions are usually managed by dose adjustment and temporary discontinuation of treatment if required, along with local symptomatic treatment.