PIRFENIDONE

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Conditions

Conditions

Condition	Modality	Targets	Highest Phase	Product
Idiopathic pulmonary fibrosis 10	Primary		Approved 8,429	ESBRIET

C_max

Value	Dose	Co-administered	Analyte	Population
6560 ng/mL	801 mg single, oral		PIRFENIDONE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
98000 ng × h/mL	801 mg single, oral		PIRFENIDONE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.75 h	801 mg single, oral		PIRFENIDONE plasma	Homo sapiens
3 h			PIRFENIDONE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
42%			PIRFENIDONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623	Disc. AE: Rash, Nausea...
2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623	Disc. AE: Weight decreased, Photosensitivity reaction...

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AEs

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AE	Significance	Dose	Population
Nausea	1.1% Disc. AE	2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623
Rash	1.3% Disc. AE	2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623
Diarrhea	3% Disc. AE	2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623
Nausea	3% Disc. AE	2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623
Photosensitivity reaction	3% Disc. AE	2403 mg 1 times / day steady, oral Recommended	unhealthy, 67 years (range: 40 - 80 years) n = 623

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 inducer 781	substrate 1,037 inhibitor 1,767 inducer 389	substrate 1,217 inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C19 1,478 CYP2E1 882 CYP2C8 911 CYP3A4/5 278 P-gp 1,461	CYP1A2 1,054 CYP1A1 349 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C18 138 CYP2C19 991 CYP2E1 667 CYP2J2 56 P-gp 1,537	CYP3A 129 CYP2C19 293 CYP3A4/5 124 CYP1A2 701

Drug as perpetrator

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Target	Modality	Activity	Metabolite
CYP1A2 1,692	inducer 1,573	no	5-carboxy-pirfenidone 1
CYP1A2 1,692	inhibitor 3,277	no	5-carboxy-pirfenidone 1
CYP2A6 739	inhibitor 3,277	no	5-carboxy-pirfenidone 1
CYP2C19 1,553	inducer 1,573	no	5-carboxy-pirfenidone 1
CYP2C19 1,553	inhibitor 3,277	no	5-carboxy-pirfenidone 1

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP1A2 1,054	substrate 3,367	major	yes (co-administration study)
CYP1A1 349	substrate 3,367	yes
CYP2A6 543	substrate 3,367	yes
CYP2B6 664	substrate 3,367	yes
CYP2C18 138	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:32016	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32016
ChemicalBook	CB5299210	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5299210
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

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PubMed

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Title	Date	PubMed
Pirfenidone inhibits early neointimal proliferation following arterial injury.	2002 Aug	12176451
Effect of pirfenidone against vanadate-induced kidney fibrosis in rats.	2002 Aug 1	12147304
Pirfenidone effectively reverses experimental liver fibrosis.	2002 Dec	12445421
Pirfenidone treatment decreases transforming growth factor-beta1 and matrix proteins and ameliorates fibrosis in chronic cyclosporine nephrotoxicity.	2002 Feb	12099512
Effect of pirfenidone on the pulmonary fibrosis of Hermansky-Pudlak syndrome.	2002 Jul	12126938

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Patents

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
Record UNII	D7NLD2JX7U
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

PIRFENIDONE

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

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

727219

Positive

EU-Orphan Drug

EU/3/04/241

Designated

FDA ORPHAN DRUG

436914

PULMONARY FIBROSIS

EMA ASSESSMENT REPORTS

ESBRIET (AUTHORISED: IDIOPATHIC PULMONARY FIBROSIS)

Established Pharmacologic Class

NDF-RT

N0000191420

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Code System

Code

Type

Description

NCI_THESAURUS

C2635

PRIMARY

FDA UNII

D7NLD2JX7U

PRIMARY

DRUG CENTRAL

4224

PRIMARY

INN

3825

PRIMARY

ChEMBL

CHEMBL1256391

PRIMARY

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Related Record

Type

Details


					1QC36BHI6S

Deupirfenidone

LABELED -> NON-LABELED

Amount:


					VK4SQL11C0

CYTOCHROME P450 1A2

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR

Amount:

48 % (average)


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

58 % (average)

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Related Record

Type

Details


					260RWO9IY8

5-CARBOXY-PIRFENIDONE

METABOLITE INACTIVE -> PARENT

Comments:

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).

Interaction Type:

MAJOR

Qualification:

PLASMA; URINE

Amount:

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Related Record

Type

Details


					D7NLD2JX7U

PIRFENIDONE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	[59 to 71] LITERS (average)	MULTIPLE DOSE ADMINISTRATION

Tmax	PHARMACOKINETIC	0.5 hours [0.5 to 4] (average)	ORAL ADMINISTRATION SINGLE DOSE 801 mg (average)

Tmax	PHARMACOKINETIC	3.5 hours (average)	FED CONDITION HIGH-FAT MEAL

Biological Half-life	PHARMACOKINETIC	3 hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator