General Information of Drug (ID: DM6VZFQ)

Drug Name
Pirfenidone
Synonyms
Deskar; Esbriet; Pirespa; Pirfenidona; Pirfenidonum; AMR 69; P 2116; AMR-69; F-647; KS-5041; Pirfenidona [INN-Spanish]; Pirfenidone (Deskar); Pirfenidone [USAN:INN]; Pirfenidonum [INN-Latin]; S-7701; Pirfenidone (JAN/USAN/INN); 5-Methyl-1-phenyl-1H-pyridin-2-one; 5-Methyl-1-phenyl-2(1H)-pyridone; 5-Methyl-1-phenyl-2-(1H)-pyridone; 5-methyl-1-phenylpyridin-2(1H)-one; 5-methyl-1-phenylpyridin-2-one
Indication
Disease Entry ICD 11 Status REF
Idiopathic pulmonary fibrosis CB03.4 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 185.22
Logarithm of the Partition Coefficient (xlogp) 1.9
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 1
ADMET Property
Absorption
The drug is rapidly absorbed following oral administration []
Half-life
The concentration or amount of drug in body reduced by one-half in 2 - 2.5 hours [2]
Vd
The volume of distribution (Vd) of drug is 70 L [3]
Chemical Identifiers
Formula
C12H11NO
IUPAC Name
5-methyl-1-phenylpyridin-2-one
Canonical SMILES
CC1=CN(C(=O)C=C1)C2=CC=CC=C2
InChI
InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
InChIKey
ISWRGOKTTBVCFA-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
40632
ChEBI ID
CHEBI:32016
CAS Number
53179-13-8
DrugBank ID
DB04951
TTD ID
D02WCI
INTEDE ID
DR1299
ACDINA ID
D00536
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Transforming growth factor beta 1 (TGFB1) TTR9XHZ TGFB1_HUMAN Modulator [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2)
Main DME
DEJGDUW CP1A2_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [6]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [7]
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [8]
Histone deacetylase 9 (HDAC9) OTO8O0LF HDAC9_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Idiopathic pulmonary fibrosis
ICD Disease Classification CB03.4
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Transforming growth factor beta 1 (TGFB1) DTT TGFB1 5.95E-09 1.68 7.81
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 7.68E-02 -2.10E-01 -6.42E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Pirfenidone (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [9]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [10]
Obeticholic acid DM3Q1SM Moderate Decreased metabolism of Pirfenidone caused by Obeticholic acid mediated inhibition of CYP450 enzyme. Autoimmune liver disease [DB96] [11]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Pirfenidone and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [12]
Osilodrostat DMIJC9X Major Decreased metabolism of Pirfenidone caused by Osilodrostat mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [9]
Ivacaftor DMZC1HS Moderate Decreased metabolism of Pirfenidone caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [13]
MK-8228 DMOB58Q Moderate Increased metabolism of Pirfenidone caused by MK-8228 mediated induction of CYP450 enzyme. Cytomegaloviral disease [1D82] [14]
Cenobamate DM8KLU9 Moderate Decreased metabolism of Pirfenidone caused by Cenobamate mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [11]
Stiripentol DMMSDOY Moderate Decreased metabolism of Pirfenidone caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [11]
Eslicarbazepine DMZREFQ Moderate Decreased metabolism of Pirfenidone caused by Eslicarbazepine mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [11]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Cannabidiol. Epileptic encephalopathy [8A62] [11]
Mirabegron DMS1GYT Moderate Decreased metabolism of Pirfenidone caused by Mirabegron mediated inhibition of CYP450 enzyme. Functional bladder disorder [GC50] [11]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Brentuximab vedotin. Hodgkin lymphoma [2B30] [15]
Etravirine DMGV8QU Moderate Decreased metabolism of Pirfenidone caused by Etravirine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Pirfenidone and Mipomersen. Hyper-lipoproteinaemia [5C80] [16]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Pirfenidone and Teriflunomide. Hyper-lipoproteinaemia [5C80] [17]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Pirfenidone and BMS-201038. Hyper-lipoproteinaemia [5C80] [18]
Givosiran DM5PFIJ Major Decreased metabolism of Pirfenidone caused by Givosiran mediated inhibition of CYP450 enzyme. Inborn porphyrin/heme metabolism error [5C58] [9]
Berotralstat DMWA2DZ Moderate Decreased metabolism of Pirfenidone caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [19]
Glycerol phenylbutyrate DMDGRQO Moderate Decreased metabolism of Pirfenidone caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme. Liver disease [DB90-DB9Z] [11]
Ceritinib DMB920Z Moderate Decreased metabolism of Pirfenidone caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [9]
PF-06463922 DMKM7EW Moderate Increased metabolism of Pirfenidone caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [9]
Dacomitinib DMOH8VY Moderate Decreased metabolism of Pirfenidone caused by Dacomitinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Capmatinib DMYCXKL Major Decreased metabolism of Pirfenidone caused by Capmatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [9]
Lumefantrine DM29GAD Moderate Decreased metabolism of Pirfenidone caused by Lumefantrine mediated inhibition of CYP450 enzyme. Malaria [1F40-1F45] [11]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [20]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Idelalisib. Mature B-cell leukaemia [2A82] [21]
Vemurafenib DM62UG5 Major Decreased metabolism of Pirfenidone caused by Vemurafenib mediated inhibition of CYP450 enzyme. Melanoma [2C30] [9]
Panobinostat DM58WKG Moderate Decreased metabolism of Pirfenidone caused by Panobinostat mediated inhibition of CYP450 enzyme. Multiple myeloma [2A83] [11]
Fedratinib DM4ZBK6 Moderate Decreased metabolism of Pirfenidone caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [11]
Rolapitant DM8XP26 Moderate Decreased metabolism of Pirfenidone caused by Rolapitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [11]
Rucaparib DM9PVX8 Major Decreased metabolism of Pirfenidone caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [9]
Abametapir DM2RX0I Moderate Decreased metabolism of Pirfenidone caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [22]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Pirfenidone caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [11]
ABIRATERONE DM8V75C Moderate Decreased metabolism of Pirfenidone caused by ABIRATERONE mediated inhibition of CYP450 enzyme. Prostate cancer [2C82] [11]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Pirfenidone and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [11]
⏷ Show the Full List of 36 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Ammonia E00007 222 Alkalizing agent
Carmellose sodium E00625 Not Available Disintegrant
Eisenoxyd E00585 56841934 Colorant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 3350 E00652 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Pirfenidone 801 mg tablet 801 mg Oral Tablet Oral
Pirfenidone 267 mg tablet 267 mg Oral Tablet Oral
Pirfenidone 267 mg capsule 267 mg Oral Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7532).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Health Canada Product Monograph: Esbriet (pirfenidone) for oral use
4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5 Risk of clinically relevant pharmacokinetic-based drug-drug interactions with drugs approved by the U.S. Food and Drug Administration between 2013 and 2016. Drug Metab Dispos. 2018 Jun;46(6):835-845.
6 Targeting the myofibroblast genetic switch: inhibitors of myocardin-related transcription factor/serum response factor-regulated gene transcription prevent fibrosis in a murine model of skin injury. J Pharmacol Exp Ther. 2014 Jun;349(3):480-6. doi: 10.1124/jpet.114.213520. Epub 2014 Apr 4.
7 Comparison of the antifibrotic effects of the pan-histone deacetylase-inhibitor panobinostat versus the IPF-drug pirfenidone in fibroblasts from patients with idiopathic pulmonary fibrosis. PLoS One. 2018 Nov 27;13(11):e0207915. doi: 10.1371/journal.pone.0207915. eCollection 2018.
8 Human precision-cut liver slices as a model to test antifibrotic drugs in the early onset of liver fibrosis. Toxicol In Vitro. 2016 Sep;35:77-85. doi: 10.1016/j.tiv.2016.05.012. Epub 2016 May 26.
9 Cerner Multum, Inc. "Australian Product Information.".
10 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
11 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
12 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
13 Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
14 Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
15 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
16 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
17 Canadian Pharmacists Association.
18 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
19 Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
20 Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
21 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
22 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.