U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H11NO
Molecular Weight 185.2218
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pirfenidone

SMILES

CC1=CN(C(=O)C=C1)C2=CC=CC=C2

InChI

InChIKey=ISWRGOKTTBVCFA-UHFFFAOYSA-N
InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3

HIDE SMILES / InChI
Molecular Formula C12H11NO
Molecular Weight 185.2218
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=12010989; http://www.ncbi.nlm.nih.gov/pubmed/?term=9435445; https://en.wikipedia.org/wiki/Pirfenidone

Pirfenidone is a synthetic antifibrotic agent indicated for the treatment of idiopathic pulmonary fibrosis as Esbriet. Pirfenidone inhibits fibroblast, epidermal, platelet-derived, and transforming beta-1 growth factors. It also inhibits DNA synthesis and the production of mRNA for collagen types I and III, resulting in a reduction in radiation-induced fibrosis. Pirfenidone has demonstrated activity in multiple fibrotic conditions however the exact mechanism of action of pirfenidone in the treatment of IPF has not been established.

CNS Activity

Originator

Approval Year

2014
503
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ESBRIET

Approved Use

Indicated for the treatment of idiopathic pulmonary fibrosis

Launch Date

2015
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7640 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/28808905
801 mg single, oral
dose: 801 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: HIGH-FAT
12600 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/28808905
801 mg single, oral
dose: 801 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
40900 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/28808905
801 mg single, oral
dose: 801 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: HIGH-FAT
49400 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/28808905
801 mg single, oral
dose: 801 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.74 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/28808905
801 mg single, oral
dose: 801 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: HIGH-FAT
2.77 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/28808905
801 mg single, oral
dose: 801 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
42%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
PIRFENIDONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Disc. AE: Rash, Nausea...
AEs leading to
discontinuation/dose reduction:
Rash (1.3%)
Nausea (1.1%)
Rash (3%)
Nausea (3%)
Diarrhea (3%)
Photosensitivity reaction (3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Disc. AE: Weight decreased, Photosensitivity reaction...
AEs leading to
discontinuation/dose reduction:
Weight decreased (0.8%)
Photosensitivity reaction (0.6%)
Respiratory failure (0.5%)
Hepatic enzyme increased (0.5%)
Bladder cancer (0.5%)
Vomiting (0.3%)
GERD (0.3%)
Malaise (0.3%)
Dysgeusia (0.3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
AEs

AEs

AESignificanceDosePopulation
Nausea 1.1%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Rash 1.3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Diarrhea 3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Nausea 3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Photosensitivity reaction 3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Rash 3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022535s000lbl.pdf
Dysgeusia 0.3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
GERD 0.3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Malaise 0.3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Vomiting 0.3%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Bladder cancer 0.5%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Hepatic enzyme increased 0.5%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Respiratory failure 0.5%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Photosensitivity reaction 0.6%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Weight decreased 0.8%
Disc. AE
2403 mg 1 times / day steady, oral
Recommended
Dose: 2403 mg, 1 times / day
Route: oral
Route: steady
Dose: 2403 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
unhealthy, 67 years (range: 40 - 80 years)
Health Status: unhealthy
Age Group: 67 years (range: 40 - 80 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/022535Orig1s000CrossR.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

inducer
1087
substrate
1193

inhibitor
2438

inducer
440
substrate
1388

inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2A6
879

CYP2C19
2057

CYP2E1
1060

CYP2C8
1057

CYP3A4/5
296

P-gp
1741
CYP1A2
1197

CYP1A1
389

CYP2A6
626

CYP2B6
776

CYP2C8
810

CYP2C18
149

CYP2C19
1119

CYP2E1
729

CYP2J2
71

P-gp
2052
CYP3A
142

CYP2C19
329

CYP3A4/5
133

CYP1A2
832
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no
5-carboxy-pirfenidone
1
CYP1A2
2333
 no
5-carboxy-pirfenidone
1
CYP2A6
911
 no
5-carboxy-pirfenidone
1
CYP2C19
2141
 no
5-carboxy-pirfenidone
1
CYP2C19
2141
 no
5-carboxy-pirfenidone
1
CYP2C8
1117
 no
5-carboxy-pirfenidone
1
CYP2C9
2497
 no
CYP2C9
2497
 no
5-carboxy-pirfenidone
1
CYP2C9
2497
 no
5-carboxy-pirfenidone
1
CYP2D6
2546
 no
5-carboxy-pirfenidone
1
CYP2E1
1146
 no
5-carboxy-pirfenidone
1
CYP3A4
2633
 no
5-carboxy-pirfenidone
1
CYP3A4/5
357
 no
CYP3A4/5
357
 no
5-carboxy-pirfenidone
1
P-gp
1932
 weak [IC50 >1000 uM]
CYP1A2
2333
 yes [Inhibition 1000 uM]
CYP2A6
911
 yes [Inhibition 1000 uM]
CYP2C19
2141
 yes [Inhibition 1000 uM]
CYP2C9
2497
 yes [Inhibition 1000 uM]
CYP2D6
2546
 yes [Inhibition 1000 uM]
CYP2E1
1146
 yes [Inhibition 1000 uM]
CYP3A4
2633
 yes [Inhibition 1000 uM]
CYP2C19
2141
 yes
CYP3A
317
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1197
 major
yes (co-administration study)
Comment: In a single-dose drug interaction study in 25 healthy nonsmokers and 25 smokers, ESBRIET was coadministered with fluvoxamine (50 mg at bedtime for 3 days; 50 mg twice a day for 3 days, and 50 mg in the morning and 100 mg at bedtime for 4 days). An approximately 4-fold increase in exposure to pirfenidone in nonsmokers and approximately 7-fold increase in exposure in smokers was observed.
Page: 6.0
CYP1A1
389
 yes
CYP2A6
626
 yes
CYP2B6
776
 yes
CYP2C18
149
 yes
CYP2C19
1119
 yes
CYP2C8
810
 yes
CYP2C9
1193
 yes
CYP2D6
1388
 yes
CYP2E1
729
 yes
CYP2J2
71
 yes
P-gp
2052
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:32016
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32016
ChemicalBook
CB5299210
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5299210
eMolecules
593320
https://www.emolecules.com/cgi-bin/more?vid=593320
MolPort
MolPort-003-666-737
https://www.molport.com/shop/molecule-link/MolPort-003-666-737
Selleck Chemicals
pirfenidone
http://www.selleckchem.com/products/pirfenidone.html
ZINC
ZINC000000001958
http://zinc15.docking.org/substances/ZINC000000001958
PubMed

PubMed

TitleDatePubMed
Pirfenidone in patients with idiopathic pulmonary fibrosis (CAPACITY): two randomised trials.
2011-05-21
A comparison of factors associated with collagen metabolism in different skeletal muscles from dystrophic (mdx) mice: impact of pirfenidone.
2007-02
Influence of pirfenidone on airway hyperresponsiveness and inflammation in a Brown-Norway rat model of asthma.
2007
Simple determination of pirfenidone in rat plasma via high-performance liquid chromatography.
2006-12
Phase II trial of pirfenidone in adults with neurofibromatosis type 1.
2006-11-28
A pilot study in patients with established advanced liver fibrosis using pirfenidone.
2006-11
Pirfenidone prevents the development of a vulnerable substrate for atrial fibrillation in a canine model of heart failure.
2006-10-17
Long-term administration of pirfenidone improves cardiac function in mdx mice.
2006-09
Pirfenidone modulates airway responsiveness, inflammation, and remodeling after repeated challenge.
2006-09
Novel pirfenidone analogues: synthesis of pyridin-2-ones for the treatment of pulmonary fibrosis.
2006-08
Pirfenidone for the treatment of idiopathic pulmonary fibrosis.
2006-07
[Newly developed therapeutic drugs for idiopathic interstitial pneumonias].
2006-06-10
Current perspectives on the treatment of idiopathic pulmonary fibrosis.
2006-06
Promising pharmacologic innovations in treating pulmonary fibrosis.
2006-06
Pirfenidone: anti-fibrotic agent with a potential therapeutic role in the management of transplantation patients.
2006-05-01
[Pulmonary fibrosis--a therapeutic dilemma?].
2006-04-15
Pirfenidone and chronic progressive obliterative airway disease.
2006-04
Therapeutic management of idiopathic pulmonary fibrosis: an evidence-based approach.
2006-03
EM703 improves bleomycin-induced pulmonary fibrosis in mice by the inhibition of TGF-beta signaling in lung fibroblasts.
2006-01-27
Pulmonary fibrosis in hermansky-pudlak syndrome. a case report and review.
2006
Sequential testing for efficacy in clinical trials with non-transient effects.
2005-11-15
The questionable efficacy of pirfenidone in IPF.
2005-11-01
Poor choice of primary outcome in a clinical trial of pirfenidone in patients with IPF.
2005-11-01
Pirfenidone for the treatment of idiopathic pulmonary fibrosis: therapeutic potential prompts further investigation.
2005-11
Gateways to clinical trials.
2005-10
Pirfenidone inhibits obliterative airway disease in mouse tracheal allografts.
2005-10
Pirfenidone inhibits inflammatory responses and ameliorates allograft injury in a rat lung transplant model.
2005-09
Expression of HSP47 in usual interstitial pneumonia and nonspecific interstitial pneumonia.
2005-06-14
[Drug treatments for idiopathic pulmonary fibrosis].
2005-06
Treatment of idiopathic pulmonary fibrosis: is there anything new?
2005-06
Pirfenidone inhibits lung allograft fibrosis through L-arginine-arginase pathway.
2005-06
The experimental agent pirfenidone reduces pro-fibrotic gene expression in a model of tacrolimus-induced nephrotoxicity.
2005-05-15
Is idiopathic pulmonary fibrosis now treatable?
2005-05-01
Double-blind, placebo-controlled trial of pirfenidone in patients with idiopathic pulmonary fibrosis.
2005-05-01
[Interstitial pneumonia].
2005-05
The novel antifibrotic agent pirfenidone attenuates the profibrotic environment generated by calcineurin inhibitors in the rat salt-depletion model.
2005-04-06
A double-blind, randomized, controlled study of oral pirfenidone for treatment of secondary progressive multiple sclerosis.
2005-04
Protection of pirfenidone against an early phase of oleic acid-induced acute lung injury in rats.
2005-04
Effect of pirfenidone on apoptosis-regulatory genes in chronic cyclosporine nephrotoxicity.
2005-02-27
[Expectation of new treatments for idiopathic interstitial pneumonias].
2005-01
Retardation of kidney failure -- applying principles to practice.
2005-01
Pirfenidone and candesartan ameliorate morphological damage in mild chronic anti-GBM nephritis in rats.
2005-01
Symptomatic and disease-modifying therapies for multiple sclerosis: recent developments: highlights of the 9th Annual Meeting of the Americas Committee for Treatment and Research in Multiple Sclerosis, October 3, 2004, Toronto, Ontario, Canada.
2005
Primary progressive multiple sclerosis : current and future treatment options.
2005
Transforming growth factor-beta: a clinical target for the treatment of diabetic nephropathy.
2004-12
The anti-fibrotic effect of pirfenidone in rat liver fibrosis is mediated by downregulation of procollagen alpha1(I), TIMP-1 and MMP-2.
2004-11
Pirfenidone inhibits the induction of iNOS stimulated by interleukin-1beta at a step of NF-kappaB DNA binding in hepatocytes.
2004-11
Effect of pirfenidone on induction of chemokines in rat hepatocytes.
2004-09
Effects of pirfenidone on endotoxin-induced liver injury after partial hepatectomy in rats.
2004-09
Modulation of articular chondrocyte activity by pirfenidone.
2003
Patents

Patents

JP2010120912A
1
US6211209
1
US6261537
11
US6264917
2
US6300349
1
US6323236
11
US6331289
5

Sample Use Guides

In Vivo Use Guide
The recommended daily maintenance dosage is 801 mg (three 267 mg capsules) three times a day with food for a total of 2403 mg/day. Doses should be taken at the same time each day. Upon initiation of treatment, titrate to the full dosage of nine capsules per day over a 14-day period as follows: 1 capsule three times days 1 through 7; 2 capsules three times a day days 8 through 14; 3 capsules three times a day days 15 onward.
Route of Administration: Oral
In Vitro Use Guide
0.01, 0.1, 0.3, and 1.0 mg/mL in in cultured myometrial and leiomyoma smooth muscle cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:41:04 GMT 2025
Edited
by admin
on Mon Mar 31 18:41:04 GMT 2025
Record UNII
D7NLD2JX7U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESBRIET
Preferred Name English
Pirfenidone
DASH   EMA EPAR   INN   JAN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
5-Methyl-1-phenyl-2(1H)-pyridone
Systematic Name English
Pirfenidone [USAN]
Common Name English
Pirfenidone [MART.]
Common Name English
2(1H)-Pyridinone, 5-methyl-1-phenyl-
Systematic Name English
Pirfenidone [EMA EPAR]
Common Name English
Pirfenidone [EP MONOGRAPH]
Common Name English
Pirfenidone [JAN]
Common Name English
Pirfenidone [WHO-DD]
Common Name English
Pirfenidone [ORANGE BOOK]
Common Name English
Pirfenidone [INN]
Common Name English
ESBRIET component pirfenidone
Brand Name English
Pirfenidone [VANDF]
Common Name English
Pirfenidone [MI]
Common Name English
AMR-69
Code English
PIRESPA
Brand Name English
NSC-748456
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 727219
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
EU-Orphan Drug EU/3/04/241
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
FDA ORPHAN DRUG 436914
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
EMA ASSESSMENT REPORTS ESBRIET (AUTHORISED: IDIOPATHIC PULMONARY FIBROSIS)
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
NDF-RT N0000191420
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
NCI_THESAURUS C797
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
WHO-ATC L04AX05
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
FDA ORPHAN DRUG 177903
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
WHO-VATC QL04AX05
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
FDA ORPHAN DRUG 411113
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C2635
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
FDA UNII
D7NLD2JX7U
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
DRUG CENTRAL
4224
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
INN
3825
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
ChEMBL
CHEMBL1256391
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
IUPHAR
7532
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
MERCK INDEX
m8876
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
PIRFENIDONE
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
PUBCHEM
40632
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
MESH
C093844
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID4045183
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
CAS
835632-50-3
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
SUPERSEDED
HSDB
8340
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
DAILYMED
D7NLD2JX7U
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
CHEBI
32016
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
RXCUI
1592254
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY RxNorm
EVMPD
SUB09907MIG
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
CAS
53179-13-8
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
NDF-RT
N0000007575
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY Pyridones [Chemical/Ingredient]
DRUG BANK
DB04951
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
SMS_ID
100000081645
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
JAPANESE REVIEW
PIRESPA
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY APPROVED OCTOBER 2008
NSC
748456
Created by admin on Mon Mar 31 18:41:04 GMT 2025 , Edited by admin on Mon Mar 31 18:41:04 GMT 2025
PRIMARY
Related Record Type Details
Structure of Deupirfenidone
LABELED -> NON-LABELED
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
MAJOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of 5-CARBOXY-PIRFENIDONE
METABOLITE INACTIVE -> PARENT
In vitro profiling studies in hepatocytes and liver microsomes have shown that ESBRIET is primarily metabolized in the liver by CYP1A2 and multiple other CYPs (CYP2C9, 2C19, 2D6, and 2E1).
MAJOR
PLASMA; URINE
Related Record Type Details
Structure of Pirfenidone
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC MULTIPLE DOSE ADMINISTRATION

Tmax PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC FED CONDITION

HIGH-FAT MEAL

Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966