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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EU EMA (2011)  |  US FDA (2014)
IUPAC Name Click here for help
5-methyl-1-phenylpyridin-2-one
International Nonproprietary Names Click here for help
INN number INN
3825 pirfenidone
Synonyms Click here for help
AMR-69 | Esbriet®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9683547
Reactome Reaction Reactome logo R-HSA-9683546
Other databases
CAS Registry No. 53179-13-8
ChEMBL Ligand CHEMBL1256391
DrugBank Ligand DB04951
DrugCentral Ligand 4224
GtoPdb PubChem SID 187051833
PubChem CID 40632
Search Google for chemical match using the InChIKey ISWRGOKTTBVCFA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ISWRGOKTTBVCFA
Search PubMed clinical trials pirfenidone
Search PubMed titles pirfenidone
Search PubMed titles/abstracts pirfenidone
UniChem Compound Search for chemical match using the InChIKey ISWRGOKTTBVCFA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ISWRGOKTTBVCFA-UHFFFAOYSA-N
Wikipedia Pirfenidone

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Pirfenidone (links to external site)
Cat. No. HY-B0673