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Merck
CN

P2116

Pirfenidone

≥97% (HPLC), powder, antifibrotic agent

Synonym(s):

5-Methyl-1-phenyl-2-(1H)-pyridone

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About This Item

Empirical Formula (Hill Notation):
C12H11NO
CAS Number:
53179-13-8
Molecular Weight:
185.22
UNSPSC Code:
12352200
PubChem Substance ID:
24278625
NACRES:
NA.77
MDL number:
MFCD00866047
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

Pirfenidone, ≥97% (HPLC)

SMILES string

O=C(C=CC(C)=C1)N1C2=CC=CC=C2

InChI key

ISWRGOKTTBVCFA-UHFFFAOYSA-N

InChI

1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3

assay

≥97% (HPLC)

form

powder

solubility

H2O: >10 mg/mL at 60 °C (warming for 30 minutes)
DMSO: >20 mg/mL

originator

Shionogi

Quality Level

100

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Application

Pirfenidone has been used:
  • as a post-operative eye drop in rabbits to analyse its antifibrotic effect to improve glaucoma filtration surgery
  • as an anti-scarring agent to examine whether it affects the foreign body reaction after glaucoma drainage device (GDD) implantation in a rabbit
  • to test its antifibrotic potential in primary cultures of human orbital fibroblasts (hOFs)
  • as tumor necrosis factor (TNFα) inhibitor to study its effect in hypoxia

Biochem/physiol Actions

Inhibits collagen production and fibroblast proliferation.
Pirfenidone inhibits collagen production and fibroblast proliferation. It has shown antifibrotic and anti-inflammatory properties in variety of animal models of pulmonary fibrosis, and in clinical trials.
Pirfenidone is used to treat idiopathic pulmonary fibrosis (IPF). It helps to decrease the weakening of lung function decline and ameliorate progression-free survival. Pirfenidone can repress the multiplication and contraction of collagen of human tenon′s fibroblasts.

Features and Benefits

This compound was developed by Shionogi. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

Pirfenidone (5-methyl-1-phenyl-2-[1H]-pyridone) is a synthetic derivative of pyridine.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000422866
0000422866
0000392029
0000392028
0000392029

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Pathobiology of Novel Approaches to Treatment
AIDS Patient Care and STDs, 26(146), 170057-170057 (2018)
Ole Hilberg et al.
The clinical respiratory journal, 6(3), 131-143 (2012-06-16)
Pirfenidone has been shown in three recently published trials to slow down the progression of the devastating interstitial lung disease, idiopathic pulmonary fibrosis (IPF). The precise mechanisms that initiate and perpetuate the histopathological process leading to lung fibrosis in IPF
Hua Zhong et al.
Investigative ophthalmology & visual science, 52(6), 3136-3142 (2011-02-19)
To investigate whether topical administration of pirfenidone eye drops could be used to prevent postoperative scarring in a rabbit model of experimental glaucoma filtration surgery. In a randomized, controlled, masked-observer study, 40 rabbits underwent trabeculectomy in the right eyes and
Suppression of TGF-beta pathway by pirfenidone decreases extracellular matrix deposition in ocular fibroblasts in vitro
Stahnke T, et al.
Testing, 12(2), e0172592-e0172592 (2017)
CX3CL1 (fractalkine) and TNF alpha production by perfused human placental lobules under normoxic and hypoxic conditions in vitro: the importance of CX3CR1 signaling
Szukiewicz D, et al.
Inflammation Research, 63(3), 179-189 (2014)
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