A pyridone derivative with antifibrotic activity
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Labeled Version(s)
26452Pirfenidone-d5
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Pirfenidone

Item No. 13986

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-methyl-1-phenyl-2(1H)-pyridinone
CAS Number
53179-13-8
Synonyms
  • AMR 69
Molecular Formula
C12H11NO
Formula Weight
185.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 17 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 3 mg/ml
λmax
203, 223, 319 nm
SMILES
CC(C=C1)=CN(C2=CC=CC=C2)C1=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $49

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    10 mg

    $93

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    50 mg

    $306

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    100 mg

    $423

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    Cayman Chemical
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    Product Description

    Pirfenidone is an orally bioavailable pyridone derivative with antifibrotic, anti-inflammatory, and antioxidant activities.1,2,3,4,5 It inhibits TGF-β1-stimulated increases in collagen type I, fibronectin, and Hsp47 expression in A549 lung cancer cells in a concentration-dependent manner.4 Pirfenidone (300 mg/kg per day) inhibits fibrosis and inhibits increases in collagen content, fibrocyte pool size, and the levels of chemokines CCL2 and CCL12 in lung in a mouse model of pulmonary fibrosis induced by bleomycin (Item No. 13877).2 In a mouse model of non-alcoholic steatohepatitis (NASH), pirfenidone inhibits fibrosis and increases in hepatocyte apoptosis, lobular inflammation, and hepatic expression of the fibrosis-related genes Col1a1, Timp1, Tgfb1, Pdgfb, and Fgf2 when administered at a dose of 280 mg/kg but has no effect on steatosis.1 Pirfenidone also inhibits NADPH-dependent lipid peroxidation in sheep liver microsomes and scavenges hydroxyl radicals (IC50s = ~6 and ~2.5 mM, respectively).3 Formulations containing pirfenidone have been used in the treatment of idiopathic pulmonary fibrosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Komiya, C., Tanaka, M., Tsuchiya, K., et al. Antifibrotic effect of pirfenidone in a mouse model of human nonalcoholic steatohepatitis. Sci. Rep. 7:44754, (2017).

    2. Inomata, M., Kamio, K., Azuma, A., et al. Pirfenidone inhibits fibrocyte accumulation in the lungs in bleomycin-induced murine pulmonary fibrosis. Respir. Res. 15:16, (2014).

    3. Misra, H.P., and Rabideau, C. Pirfenidone inhibits NADPH-dependent microsomal lipid peroxidation and scavenges hydroxyl radicals. Mol. Cell. Biochem. 204(1-2), 119-126 (2000).

    4. Hisatomi, K., Mukae, H., Sakamoto, N., et al. Pirfenidone inhibits TGF-β1-induced over-expression of collagen type I and heat shock protein 47 in A549 cells. BMC Pulm. Med. 12:24, (2012).

    5. Moeller, A., Ask, K., Warburton, D., et al. The bleomycin animal model: A useful tool to investigate treatment options for idiopathic pulmonary fibrosis? Int. J. Biochem. Cell Biol. 40(3), 362-382 (2008).