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P2116

Sigma-Aldrich

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
MDL number:
MFCD00866047
UNSPSC Code:
12352200
PubChem Substance ID:
24278625
NACRES:
NA.77

product name

Pirfenidone, ≥97% (HPLC)

Assay

≥97% (HPLC)

form

powder

solubility

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

originator

Shionogi

SMILES string

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

InChI

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

InChI key

ISWRGOKTTBVCFA-UHFFFAOYSA-N

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General description

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

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pirfenidone safety and adverse event management in idiopathic pulmonary fibrosis
Lancaster L H, et al.
European Respiratory Review, 26(146), 170057-170057 (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)
Arata Azuma
Therapeutic advances in respiratory disease, 6(2), 107-114 (2012-02-16)
Pirfenidone is the first antifibrotic agent to be approved for the treatment of pulmonary fibrosis. Idiopathic pulmonary fibrosis (IPF) is one of the idiopathic interstitial pneumonias with the worst prognoses; approximately half of patients die within 3-5 years, and the
Huzaifa I Adamali et al.
Drug design, development and therapy, 6, 261-272 (2012-10-12)
Over the past decade, there has been a cohesive effort from patients, physicians, clinical and basic scientists, and the pharmaceutical industry to find definitive treatments for idiopathic pulmonary fibrosis (IPF). As understanding of disease behavior and pathogenesis has improved, the
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)
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