Pirfenidone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Pirfenidone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Pirfenidone?

The molecule Pirfenidone presents a molecular formula of C12H11NO and its IUPAC name is 5-methyl-1-phenylpyridin-2-one.

Pirfenidone (INN) is a medication used to treat idiopathic pulmonary fibrosis. It is a synthetic antifibrotic agent and works by inhibiting the production of transforming growth factor beta (TGF-β)..

Pirfenidone was originally developed by Mukaide Chemical Industries in Japan and is currently marketed under the brand name Esbriet by Roche. It is approved for use in Japan, South Korea, Europe, Canada, and India..

The most common side effects of pirfenidone are gastrointestinal in nature, such as nausea, vomiting, and diarrhea. Other side effects include skin rashes, photosensitivity, and headache..

Pirfenidone has been shown to be effective in slowing the progression of idiopathic pulmonary fibrosis in clinical trials. The medication is typically taken three times daily..

There is no cure for idiopathic pulmonary fibrosis, but pirfenidone can help improve symptoms and quality of life for patients with this debilitating disease..

3D structure

Cartesian coordinates

Geometry of Pirfenidone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Pirfenidone ISWRGOKTTBVCFA-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Pirfenidone

 

Molecule descriptors

 
IUPAC name5-methyl-1-phenylpyridin-2-one
InChI codeInChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
InChI KeyISWRGOKTTBVCFA-UHFFFAOYSA-N
SMILESCc1ccc(=O)n(-c2ccccc2)c1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1-phenyl-5-methyl-2-pyridinone
  • 179P138
  • 2(1H)-Pyridinone, 5-methyl-1-phenyl-
  • 2(1H)-Pyridone, 5-methyl-1-phenyl-
  • 5-Methyl-1-phenyl-1H-pyridin-2-one
  • 5-Methyl-1-phenyl-2(1H)-pyridone
  • 5-Methyl-1-phenyl-2-(1H)-pyridone
  • 5-Methyl-1-phenyl-2-pyridone
  • 5-methyl-1-phenyl-2(1H)-pyridinone
  • 5-methyl-1-phenyl-2-pyridinone
  • 5-methyl-1-phenyl-pyridin-2-one
  • 5-methyl-1-phenylpyridin-2(1H)-one
  • 5-methyl-1-phenylpyridin-2-one
  • 53179-13-8
  • A829431
  • AB07515
  • AC-6797
  • AM84939
  • AMR 69
  • AMR-69
  • AMR69
  • B2288
  • BCP04473
  • BDBM50005201
  • BM164275
  • BRN 1526549
  • Bio1_000397
  • Bio1_000886
  • Bio1_001375
  • CCG-204989
  • D01583
  • D7NLD2JX7U
  • DB04951
  • DSSTox_CID_25183
  • DSSTox_GSID_45183
  • DSSTox_RID_80731
  • Deskar
  • ESBRIET COMPONENT PIRFENIDONE
  • EU-0100907
  • Esbriet
  • F-647
  • FT-0602686
  • FT-0672092
  • GTPL7532
  • HMS2234G24
  • HMS3262F16
  • HMS3267I06
  • HMS3372A08
  • HMS3412G13
  • HMS3651P08
  • HMS3676G13
  • HSDB 8340
  • HY-B0673
  • J-523979
  • KS-5041
  • LP00907
  • Lopac-P-2116
  • Lopac0_000907
  • MFCD00866047
  • MLS000860042
  • NCGC00015806-01
  • NCGC00015806-02
  • NCGC00015806-03
  • NCGC00015806-04
  • NCGC00015806-05
  • NCGC00015806-06
  • NCGC00015806-17
  • NCGC00024992-01
  • NCGC00024992-02
  • NCGC00024992-03
  • NCGC00261592-01
  • NSC 748456
  • NSC-748456
  • NSC748456
  • P 2116
  • P1871
  • PIRFENIDONE
  • PIRFENIDONE COMPONENT OF ESBRIET
  • Pirespa
  • Pirfenidona
  • Pirfenidone
  • Pirfenidone (JAN/USAN/INN)
  • Pirfenidone(AMR69)
  • Pirfenidone- Bio-X
  • Pirfenidone-[d3]
  • Pirfenidonum
  • Prfendone
  • Q2060696
  • S-7701
  • S-7701,AMR-69
  • SDCCGSBI-0050882.P002
  • SMR000326900
  • SR-01000076061
  • SR-01000076061-1
  • SR-01000076061-3
  • SW220156-1
  • SY034783
  • Tocris-1093
  • Tox21 110225
  • s2907

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1958
  • CAS-53179-13-8
  • UNII-D7NLD2JX7U
  • AKOS006273697
  • BRD-K96862998-001-03-1
  • BRD-K96862998-001-09-8
  • DTXSID4045183
  • CHEMBL1256391
  • CHEBI:32016
  • Tox21_110225
  • Tox21_500907
  • Tox21_110225_1
  • SCHEMBL4708

Physico-Chemical properties

IUPAC name5-methyl-1-phenylpyridin-2-one
Molecular formulaC12H11NO
Molecular weight185.222
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity57.01
LogP2.1
Topological polar surface area22.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.