Pirfenidone

Modify Date: 2024-01-02 14:05:46

Pirfenidone structure	Common Name	Pirfenidone
	CAS Number	53179-13-8	Molecular Weight	185.222
	Density	1.1±0.1 g/cm3	Boiling Point	329.1±15.0 °C at 760 mmHg
	Molecular Formula	C₁₂H₁₁NO	Melting Point	96-97ºC
	MSDS	Chinese USA	Flash Point	152.7±11.6 °C
	Symbol	GHS07	Signal Word	Warning

Use of Pirfenidone

Pirfenidone is a drug used for the treatment of idiopathic pulmonary fibrosis. It inhibits FGFR, EGFR, PDGFR, TGF-β, thereby slowing tumor cell proliferation.

Name	pirfenidone
Synonym	More Synonyms

Description	Pirfenidone is a drug used for the treatment of idiopathic pulmonary fibrosis. It inhibits FGFR, EGFR, PDGFR, TGF-β, thereby slowing tumor cell proliferation.
Related Catalog	Signaling Pathways >> Stem Cell/Wnt >> TGF-beta/Smad Signaling Pathways >> TGF-beta/Smad >> TGF-beta/Smad Research Areas >> Inflammation/Immunology
Target	TGF-β2[1]
In Vitro	Pirfenidone (PFD) reduces the protein levels of the matrix metalloproteinase (MMP)-11, a TGF-β target gene and furin substrate involved in carcinogenesis. These data define PFD or PFD-related agents as promising agents for human cancers associated with enhanced TGF-β activity[1]. In RAW264.7 cells, a murine macrophage-like cell line, Pirfenidone suppresses the proinflammatory cytokine TNF-α by a translational mechanism, which is independent of activation of the MAPK2, p38 MAPK, and JNK. In the murine endotoxin shock model, Pirfenidone potently inhibits the production of the proinflammatory cytokines, TNF-α, interferon-γ, and interleukin-6, but enhances the production of the anti-inflammatory cytokine, interleukin-10[2]. Pirfenidone (PFD) shows its inhibitory effects on the proliferation of HLECs. Cell proliferation is attenuated in the 0.3 mg/mL group after 24 hours compare with the control group (P=0.044). The effect is more apparent in the 0.5 mg/mL group at 24, 48, and 72 hours (P<0.05). The proliferation is almost completely inhibited with 1 mg/mL PFD at all the time-points (P<0.01)[3].
In Vivo	Administration of Pirfenidone (300 mg/kg/day) for 4 wk. Pirfenidone significantly attenuates the score when administered in Bleomycin (BLM)-treated mice (P<0.0001). Moreover, collagen content is quantified in the lungs to evaluate the anti-fibrotic effects of Pirfenidone. The collagen content in the lungs of BLM-treated mice is significantly increased compared with that in saline- or Pirfenidone-treated mice, and this increase is significantly attenuated by Pirfenidone administration on day 28 after BLM treatment (P=0.0012)[4].
Cell Assay	HLECs are seeded in 96-well plates (1×104 cells/well) for 24 hours in α-MEM/10% FBS/1%NEAA, and are cultured in stationary tubes in serum-free medium for 24 hours. And then the culture medium is removed and cells are bathed in α-MEM with 10% FBS and 1% NEAA supplemented with 0, 0.01, 0.1, 0.2, 0.3, 0.5, or 1 mg/mL Pirfenidone for 0, 4, 12, 24, 48, or 72 hours. After incubation with 180 µL α-MEM and 20 µL of 5 mg/mL MTT for 4 hours at 37°C, the MTT solution is discarded. The Formosan precipitates are dissolved in 180 µL DMSO by agitating the dishes for 10 minutes at 200 rpm on an orbital shaker. The absorbance at 490 nm in each well is read with a micro plate reader. We further examined the effects of PFD by refining the concentrations at 0.2, 0.25, 0.3, 0.4, 0.5 and 0.6 mg/mL using the MTT assay[3].
Animal Admin	Mice[4] Nine-week-old female C57BL/6 mice are used. Pirfenidone is administered orally for 14 days after osmotic pump implantation. The volume of administration is determined according to body weight. Animals are allocated into 4 groups (n=6/group): normal control, BLM, Pirfenidone (300 mg/kg/day), and BLM + Pirfenidone. The Pirfenidone dose is selected according to a report published elsewhere. Pirfenidone is also administered in a therapeutic setting beginning at day 10 to assess the effect of the drug on the fibrotic phase of BLM model mice.
References	[1]. Burghardt I, et al. Pirfenidone inhibits TGF-beta expression in malignant glioma cells. Biochem Biophys Res Commun. 2007 Mar 9;354(2):542-7. [2]. Nakazato H, et al. A novel anti-fibrotic agent pirfenidone suppresses tumor necrosis factor-alpha at the translational level. Eur J Pharmacol. 2002 Jun 20;446(1-3):177-85. [3]. Yang Y, et al. Inhibition of Pirfenidone on TGF-beta2 induced proliferation, migration and epithlial-mesenchymal transitionof human lens epithelial cells line SRA01/04. PLoS One. 2013;8(2):e56837. [4]. Inomata M, et al. Pirfenidone inhibits fibrocyte accumulation in the lungs in bleomycin-induced murine pulmonary fibrosis. Respir Res. 2014 Feb 8;15:16. [5]. Brooks D, et al. Limited fibrosis accompanies triple-negative breast cancer metastasis in multiple model systems and is not a preventive target. Oncotarget. 2018 May 4;9(34):23462-23481.

Density	1.1±0.1 g/cm3
Boiling Point	329.1±15.0 °C at 760 mmHg
Melting Point	96-97ºC
Molecular Formula	C₁₂H₁₁NO
Molecular Weight	185.222
Flash Point	152.7±11.6 °C
Exact Mass	185.084061
PSA	22.00000
LogP	1.82
Appearance of Characters	solid
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.592
Storage condition	Store at RT
Water Solubility	DMSO: ≥10 mg/mL, soluble

Pirfenidone MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV1148200

CHEMICAL NAME :: 2(1H)-Pyridone, 5-methyl-1-phenyl-

CAS REGISTRY NUMBER :: 53179-13-8

BEILSTEIN REFERENCE NO. :: 1526549

LAST UPDATED :: 199612

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C12-H11-N-O

MOLECULAR WEIGHT :: 185.24

WISWESSER LINE NOTATION :: T6NVJ AR& E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1295 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 430 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 580 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4042699

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 420 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3974281

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 285 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 810 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 460 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #383591

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn:Harmful;
Risk Phrases	R22
Safety Phrases	S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	UV1148200
HS Code	2933399090

2-Hydroxy-5-picoline

CAS#:1003-68-5

Iodobenzene

CAS#:591-50-4

~56%

Pirfenidone

CAS#:53179-13-8

Literature: AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; SOMMERS, Andreas Patent: WO2012/122165 A2, 2012 ; Location in patent: Page/Page column 62 ;

Bromobenzene

CAS#:108-86-1

2-Hydroxy-5-picoline

CAS#:1003-68-5

Pirfenidone

CAS#:53179-13-8

Literature: WO2010/141600 A2, ; Page/Page column 13-14 ;

4-Bromoanisole

CAS#:104-92-7

2-Hydroxy-4-picoline

CAS#:13466-41-6

Pirfenidone

CAS#:53179-13-8

Literature: US2008/161361 A1, ; Page/Page column 8-9 ;

2-Hydroxy-5-picoline

CAS#:1003-68-5

Triphenylbismuth

CAS#:603-33-8

~98%

Pirfenidone

CAS#:53179-13-8

Literature: Crifar, Cynthia; Petiot, Pauline; Ahmad, Tabinda; Gagnon, Alexandre Chemistry - A European Journal, 2014 , vol. 20, # 10 p. 2755 - 2760

2-Hydroxy-5-picoline

CAS#:1003-68-5

Iodobenzene

CAS#:591-50-4

N/A

CAS#:12775-96-1

Pirfenidone

CAS#:53179-13-8

Literature: US3974281 A1, ; US 3974281 A

2-Hydroxy-5-picoline

CAS#:1003-68-5

Phenylboronic acid

CAS#:98-80-6

~11%

Pirfenidone

CAS#:53179-13-8

Literature: Kader, Kamelia F. Abd El; Bialy, Serry A.A. El; El-Ashmawy, Mahmoud B.; Boykin, David W. Heterocyclic Communications, 2012 , vol. 18, # 4 p. 193 - 197

Precursor 7
CAS#:1003-68-5 2-Hydroxy-5-picoline CAS#:591-50-4 Iodobenzene CAS#:108-86-1 Bromobenzene CAS#:104-92-7 4-Bromoanisole
CAS#:13466-41-6 2-Hydroxy-4-picoline CAS#:603-33-8 Triphenylbismuth CAS#:98-80-6 Phenylboronic acid
DownStream 0

HS Code	2933399090
Summary	2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Lung fibrosis: drug screening and disease biomarker identification with a lung slice culture model and subtracted cDNA Library.

Altern. Lab. Anim. 42(4) , 235-43, (2014)

Pulmonary fibrosis is a progressive and irreversible disorder with no appropriate cure. A practical and effective experimental model that recapitulates the disease will greatly benefit the research co...

A novel genomic signature with translational significance for human idiopathic pulmonary fibrosis.

Am. J. Respir. Cell. Mol. Biol. 52(2) , 217-31, (2015)

The bleomycin-induced rodent lung fibrosis model is commonly used to study mechanisms of lung fibrosis and to test potential therapeutic interventions, despite the well recognized dissimilarities to h...

Local delivery of biodegradable pirfenidone nanoparticles ameliorates bleomycin-induced pulmonary fibrosis in mice.

Nanotechnology 23(50) , 505101, (2012)

Our purpose was to assess sustained delivery and enhanced efficacy of pirfenidone-loaded nanoparticles after intratracheal instillation.Poly(lactide-co-glycolide) nanoparticles containing pirfenidone ...

TORASEMIDETECHPIRFENIDONE

5-Methyl-1-phenyl-2-(1H)-pyridone

2(1H)-Pyridinone, 5-methyl-1-phenyl-

5-methyl-1-phenyl-2-pyridone

5-Methyl-N-phenyl-2-1H-pyridone

Pirespa

S-7701

amr-69

5-methyl-1-phenyl-1H-pyridin-2-one

5-Methyl-1-phenyl-2(1H)-pyridinone

5-methyl-1-phenyl-pyridin-2-one

Etuary

5-Methyl-1-phenylpyridin-2(1H)-one

MFCD00866047

Pirfenidone

5-21-07-00197 (Beilstein Handbook Reference)

Esbriet

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