pirfenidone   Click here for help

GtoPdb Ligand ID: 7532

Synonyms: AMR-69 | Esbriet®
Approved drug Immunopharmacology Ligand
pirfenidone is an approved drug (EMA (2011), FDA (2014))
Compound class: Synthetic organic
Comment: Pirfenidone is an anti-fibrotic drug. In addition to its proven anti-fibrotic effects in lung tissue, pirfenidone-induced in vitro and in vivo anti-fibrotic activity has been reported in experimental liver and renal fibrosis [3,5].

SARS-CoV-2: COVID-19 is accompanied by inflammation and fibrotic lung damage that appears to persist beyond immediate recovery. The clinical potential for applying the antifibrotic activity of pirfenidone to help treat COVID-19-related pulmonary fibrosis is reviewed by Ferrara et al. (2020) [2].

pirfenidone is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 21.48
Molecular weight 185.08
XLogP 3.08
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Cc1ccc(=O)n(c1)c1ccccc1
Isomeric SMILES Cc1ccc(=O)n(c1)c1ccccc1
InChI 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
References
1. Conte E, Gili E, Fagone E, Fruciano M, Iemmolo M, Vancheri C. (2014)
Effect of pirfenidone on proliferation, TGF-β-induced myofibroblast differentiation and fibrogenic activity of primary human lung fibroblasts.
Eur J Pharm Sci, 58: 13-9. [PMID:24613900]
2. Ferrara F, Granata G, Pelliccia C, La Porta R, Vitiello E. (2020)
The added value of pirfenidone to fight inflammation and fibrotic state induced by SARS-CoV-2.
European Journal of Clinical Pharmacology,. DOI: 10.1007/s00228-020-02947-4
3. García L, Hernández I, Sandoval A, Salazar A, Garcia J, Vera J, Grijalva G, Muriel P, Margolin S, Armendariz-Borunda J. (2002)
Pirfenidone effectively reverses experimental liver fibrosis.
J Hepatol, 37 (6): 797-805. [PMID:12445421]
4. King Jr TE, Bradford WZ, Castro-Bernardini S, Fagan EA, Glaspole I, Glassberg MK, Gorina E, Hopkins PM, Kardatzke D, Lancaster L et al.. (2014)
A phase 3 trial of pirfenidone in patients with idiopathic pulmonary fibrosis.
N Engl J Med, 370 (22): 2083-92. [PMID:24836312]
5. Macías-Barragán J, Sandoval-Rodríguez A, Navarro-Partida J, Armendáriz-Borunda J. (2010)
The multifaceted role of pirfenidone and its novel targets.
Fibrogenesis Tissue Repair, 3: 16. [PMID:20809935]