Pirfenidone
Identification
- Name
- Pirfenidone
- Accession Number
- DB04951
- Description
Pirfenidone is an orally active small molecule drug that may inhibit collagen synthesis, down regulate production of multiple cytokines and block fibroblast proliferation and stimulation in response to cytokines. Pirfenidone has demonstrated activity in multiple fibrotic conditions, including those of the lung, kidney and liver. It is being investigated by InterMune.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Pirfenidone (DB04951)
- Weight
- Average: 185.2218
Monoisotopic: 185.084063979 - Chemical Formula
- C12H11NO
- Synonyms
- pirfenidona
- Pirfenidone
- External IDs
- AMR-69
Pharmacology
- Indication
For the treatment of idiopathic pulmonary fibrosis (IPF).
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Pirfenidone is a novel agent with anti-inflammatory, antioxidant, and antifibrotic properties. It may improve lung function and reduce the number of acute exacerbations in patients with idiopathic pulmonary fibrosis (IPF).
- Mechanism of action
Pirfenidone is an orally active, small molecule that shows a wide range of biologic activity. In vitro evidence has shown that pirfenidone inhibits collagen synthesis, down-regulates profibrotic cytokines and decreases fibroblast proliferation. Pirfenidone leads to a reduction of TGF-beta2 mRNA levels and of the mature TGF-beta2 protein due to decreased expression and direct inhibition of the TGF-beta pro-protein convertase furin. In addition, pirfenidone reduces the protein levels of the matrix metalloproteinase (MMP)-11, a TGF-beta target gene and furin substrate involved in carcinogenesis.
Target Actions Organism UFurin Not Available Humans - Absorption
Rapidly absorbed following oral administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
2-2.5 hours
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Generally well tolerated with the most frequent side effects reported being photosensitivity rash and gastrointestinal symptoms.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Pirfenidone can be increased when it is combined with Abametapir. Abatacept The metabolism of Pirfenidone can be increased when combined with Abatacept. Abiraterone The serum concentration of Pirfenidone can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Pirfenidone. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Pirfenidone. Acyclovir The metabolism of Acyclovir can be decreased when combined with Pirfenidone. Adalimumab The metabolism of Pirfenidone can be increased when combined with Adalimumab. Adenovirus type 7 vaccine live The risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Pirfenidone. Agomelatine The metabolism of Agomelatine can be decreased when combined with Pirfenidone. Albendazole The metabolism of Albendazole can be decreased when combined with Pirfenidone. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take at the same time every day.
- Take with food. This may reduce the adverse effects of nausea and dizziness. Food also impacts the bioavailability of pirfenidone.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataEsbriet Tablet, coated 267 mg/1 Oral Genentech, Inc. 2017-01-11 Not applicable US 
Esbriet Capsule 267 mg Oral Roche Registration Gmb H 2011-02-28 Not applicable EU 
Esbriet Capsule 267 mg Oral Hoffmann La Roche 2013-01-08 Not applicable Canada 
Esbriet Capsule 267 mg Oral Roche Registration Gmb H 2011-02-28 Not applicable EU Esbriet Capsule 267 mg/1 Oral Genentech, Inc. 2014-10-15 Not applicable US Esbriet Tablet 801 mg Oral Hoffmann La Roche 2017-07-26 Not applicable Canada Esbriet Capsule 267 mg Oral Roche Registration Gmb H 2011-02-28 Not applicable EU Esbriet Tablet, coated 801 mg/1 Oral Genentech, Inc. 2017-01-11 Not applicable US Esbriet Capsule 267 mg/1 Oral Inter Mune 2014-10-16 Not applicable US Esbriet Tablet 267 mg Oral Hoffmann La Roche 2017-07-26 Not applicable Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- ATC Codes
- L04AX05 — Pirfenidone
- Drug Categories
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Antifibrotic Agents
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Antirheumatic Agents
- Central Nervous System Agents
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Immunosuppressive Agents
- Peripheral Nervous System Agents
- Pyridines
- Pyridones
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyridinones. These are compounds containing a pyridine ring, which bears a ketone.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Hydropyridines
- Direct Parent
- Pyridinones
- Alternative Parents
- Methylpyridines / Dihydropyridines / Benzene and substituted derivatives / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Dihydropyridine / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Methylpyridine / Monocyclic benzene moiety / Organic nitrogen compound show 6 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- ring assembly, pyridone (CHEBI:32016)
Chemical Identifiers
- UNII
- D7NLD2JX7U
- CAS number
- 53179-13-8
- InChI Key
- ISWRGOKTTBVCFA-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
- IUPAC Name
- 5-methyl-1-phenyl-1,2-dihydropyridin-2-one
- SMILES
- CC1=CN(C(=O)C=C1)C1=CC=CC=C1
References
- General References
- Hale ML, Margolin SB, Krakauer T, Roy CJ, Stiles BG: Pirfenidone blocks the in vitro and in vivo effects of staphylococcal enterotoxin B. Infect Immun. 2002 Jun;70(6):2989-94. [PubMed:12010989]
- Shi S, Wu J, Chen H, Chen H, Wu J, Zeng F: Single- and multiple-dose pharmacokinetics of pirfenidone, an antifibrotic agent, in healthy Chinese volunteers. J Clin Pharmacol. 2007 Oct;47(10):1268-76. [PubMed:17906160]
- External Links
- PubChem Compound
- 40632
- PubChem Substance
- 175426915
- ChemSpider
- 37115
- BindingDB
- 50005201
- 1592254
- ChEBI
- 32016
- ChEMBL
- CHEMBL1256391
- ZINC
- ZINC000000001958
- Wikipedia
- Pirfenidone
- AHFS Codes
- 48:02.00 — Antifibrotic Agents
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Idiopathic Pulmonary Fibrosis (IPF) 3 4 Recruiting Treatment Progressive Idiopathic Pulmonary Fibrosis 1 4 Unknown Status Treatment Acute Kidney Injury (AKI) / Sepsis 1 4 Unknown Status Treatment Dermatopolymyositis / Interstitial Lung Diseases (ILD) 1 4 Unknown Status Treatment Sarcoidosis, Pulmonary 1 3 Active Not Recruiting Treatment Albuminuria / Nephropathy, Diabetic 1 3 Completed Treatment Diabetic Foot Ulcers (DFU) 1 3 Completed Treatment Idiopathic Pulmonary Fibrosis (IPF) 5 3 Recruiting Treatment Dermatomyositis Interstitial Lung Disease (Dm-ILD) 1 3 Recruiting Treatment Novel Coronavirus Pneumonia / Pirfenidone / Pneumonia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 267 mg/1 Capsule Oral 267 mg Tablet Oral 267 mg Tablet Oral 801 mg Tablet, coated Oral 267 mg/1 Tablet, coated Oral 801 mg/1 Tablet, film coated Oral 267 MG Tablet, film coated Oral 534 MG Tablet, film coated Oral 801 MG Tablet, coated Oral 267 mg Tablet, coated Oral 801 mg Capsule, coated Oral 267 mg Capsule Oral Tablet, film coated Oral 200 mg Capsule Oral 200 mg Tablet, coated Oral 400 mg Tablet, coated Oral 600 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7988994 No 2011-08-02 2026-09-22 US US7816383 No 2010-10-19 2030-01-08 US US8013002 No 2011-09-06 2030-01-08 US US8084475 No 2011-12-27 2030-01-08 US US8778947 No 2014-07-15 2033-08-30 US US7566729 No 2009-07-28 2029-04-22 US US7767225 No 2010-08-03 2026-09-22 US US7635707 No 2009-12-22 2029-04-22 US US7767700 No 2010-08-03 2027-12-18 US US8592462 No 2013-11-26 2029-04-22 US US8383150 No 2013-02-26 2026-09-22 US US8318780 No 2012-11-27 2030-01-08 US US8420674 No 2013-04-16 2027-12-18 US US7910610 No 2011-03-22 2030-01-08 US US8648098 No 2014-02-11 2030-01-08 US US8754109 No 2014-06-17 2030-01-08 US US8609701 No 2013-12-17 2029-04-22 US US8753679 No 2014-06-17 2026-09-22 US US7696236 No 2010-04-13 2027-12-18 US US9561217 No 2017-02-07 2022-01-25 US US10188637 No 2019-01-29 2037-03-28 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
Learn more
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.89 mg/mL ALOGPS logP 2 ALOGPS logP 2.14 ChemAxon logS -1.8 ALOGPS pKa (Strongest Basic) -1.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 20.31 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 57 m3·mol-1 ChemAxon Polarizability 20.28 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier + 0.996 Caco-2 permeable + 0.8614 P-glycoprotein substrate Non-substrate 0.8193 P-glycoprotein inhibitor I Non-inhibitor 0.755 P-glycoprotein inhibitor II Non-inhibitor 0.9177 Renal organic cation transporter Non-inhibitor 0.8157 CYP450 2C9 substrate Non-substrate 0.6638 CYP450 2D6 substrate Non-substrate 0.8248 CYP450 3A4 substrate Substrate 0.6111 CYP450 1A2 substrate Inhibitor 0.9108 CYP450 2C9 inhibitor Non-inhibitor 0.5982 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.7166 CYP450 3A4 inhibitor Non-inhibitor 0.775 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7633 Ames test Non AMES toxic 0.7652 Carcinogenicity Non-carcinogens 0.8992 Biodegradation Not ready biodegradable 0.9112 Rat acute toxicity 2.1330 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9784 hERG inhibition (predictor II) Non-inhibitor 0.6301
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-000i-2900000000-b9809376eba9769e9bee
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Furin is likely to represent the ubiquitous endoprotease activity within constitutive secretory pathways and capable of cleavage at the RX(K/R)R consensus motif.
- Gene Name
- FURIN
- Uniprot ID
- P09958
- Uniprot Name
- Furin
- Molecular Weight
- 86677.375 Da
References
- Burghardt I, Tritschler F, Opitz CA, Frank B, Weller M, Wick W: Pirfenidone inhibits TGF-beta expression in malignant glioma cells. Biochem Biophys Res Commun. 2007 Mar 9;354(2):542-7. Epub 2007 Jan 10. [PubMed:17234158]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Arai T, Inoue Y, Sasaki Y, Tachibana K, Nakao K, Sugimoto C, Okuma T, Akira M, Kitaichi M, Hayashi S: Predictors of the clinical effects of pirfenidone on idiopathic pulmonary fibrosis. Respir Investig. 2014 Mar;52(2):136-43. doi: 10.1016/j.resinv.2013.09.002. Epub 2013 Oct 24. [PubMed:24636270]
- Pirfenidone FDA label [File]
Drug created on October 21, 2007 16:23 / Updated on November 23, 2020 09:08
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