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:
Molecular Weight:
185.22
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Product Name
Pirfenidone, ≥97% (HPLC)
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Natalie J Carter
Drugs, 71(13), 1721-1732 (2011-09-10)
Pirfenidone is an orally administered pyridine that has orphan designation for the treatment of mild to moderate idiopathic pulmonary fibrosis (IPF) in the EU. Pirfenidone 2403 mg/day for 72 weeks administered to patients with IPF was associated with a significantly lower
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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
Peyman Bizargity et al.
Transplantation, 94(2), 114-122 (2012-06-30)
Pirfenidone (PFD) is an antifibrotic agent with beneficial effects on proinflammatory disorders. In this study, we further investigated PFD and long-acting form, "deuterated PFD," immune-modulating properties by evaluating their effects on mouse dendritic cells (DCs). The effects of PFD on
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