Pirfenidone

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

Pirfenidone Structure
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
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.

 Names

Name pirfenidone
Synonym More Synonyms

 Pirfenidone Biological Activity

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
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.

 Chemical & Physical Properties

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

 Toxicological Information

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

 Safety Information

Symbol GHS07
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

 Synthetic Route

2-Hydroxy-5-picoline structure

2-Hydroxy-5-picoline

CAS#:1003-68-5

Iodobenzene structure

Iodobenzene

CAS#:591-50-4

~56%

Pirfenidone Structure

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 structure

Bromobenzene

CAS#:108-86-1

2-Hydroxy-5-picoline structure

2-Hydroxy-5-picoline

CAS#:1003-68-5

~%

Pirfenidone Structure

Pirfenidone

CAS#:53179-13-8

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

4-Bromoanisole

CAS#:104-92-7

2-Hydroxy-4-picoline structure

2-Hydroxy-4-picoline

CAS#:13466-41-6

~%

Pirfenidone Structure

Pirfenidone

CAS#:53179-13-8

Literature: US2008/161361 A1, ; Page/Page column 8-9 ;
2-Hydroxy-5-picoline structure

2-Hydroxy-5-picoline

CAS#:1003-68-5

Triphenylbismuth structure

Triphenylbismuth

CAS#:603-33-8

~98%

Pirfenidone Structure

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 structure

2-Hydroxy-5-picoline

CAS#:1003-68-5

Iodobenzene structure

Iodobenzene

CAS#:591-50-4

N/A structure

N/A

CAS#:12775-96-1

~%

Pirfenidone Structure

Pirfenidone

CAS#:53179-13-8

Literature: US3974281 A1, ; US 3974281 A
2-Hydroxy-5-picoline structure

2-Hydroxy-5-picoline

CAS#:1003-68-5

Phenylboronic acid structure

Phenylboronic acid

CAS#:98-80-6

~11%

Pirfenidone Structure

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

 Customs

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%

 Articles69

More Articles
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 ...

 Synonyms

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
Top Suppliers:I want be here

Get all suppliers and price by the below link:

Pirfenidone suppliers

Price: ￥452.4/100mg

Reference only. check more Pirfenidone price

Related Compounds: More...
Pirfenidone D5
1020719-62-3
4-Bromo Pirfenidone
377756-15-5
3-Bromo Pirfenidone
912570-13-9
5-carboxy-pirfenidone
77837-08-2
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
1-(1H-pyrrol-2-yl)prop-2-en-1-ol
1538421-05-4
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
849349-65-1
Chemsrc provides Pirfenidone(CAS#:53179-13-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Pirfenidone are included as well.>> amp version: Pirfenidone

Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved