Drug General Information (ID: D1299)
  Drug Name
Pirfenidone
  Drug Type Small molecule
  Drug Synonymous
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
    Click to Show/Hide
  Disease Class CB03: Idiopathic interstitial pneumonitis
  Therapeutic Class Pulmonary Fibrosis Inhibitors
  Structure Could Not Find 2D Structure
3D Structure 2D Structure
  Formula C12H11NO
  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
  Canonical SMILES CC1=CN(C(=O)C=C1)C2=CC=CC=C2
  External Link
Pubchem ID 40632
CAS Number 53179-13-8
CHEBI ID 32016
TTD ID D02WCI
INTEDE ID DR1299

Drug-Drug Interaction Network
  Sunburst Graph
AM004  Affected intra/extra-hepatic metabolism
AM006  Pharmacodynamic additive effects
BM017  CYP450 enzyme inhibition
BM022  CYP450 enzyme induction
BM055  Increased risk of hepatotoxicity
BM075  Increased risk of photosensitivity reactions
  Relation Graph
 Full list of drugs interacting with Pirfenidone
      Affected intra/extra-hepatic metabolism
   CYP450 enzyme inhibition Drug Num:  69
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0066
 
Amiodarone
 
C25H29I2NO3
 
2157 
Major    Inter Info   
[3], [4], [5]
D0341
 
Ciprofloxacin
 
C17H18FN3O3
 
2764 
Major    Inter Info   
[4], [5]
D0573
 
Enoxacin
 
C15H17FN4O3
 
3229 
Major    Inter Info   
[4], [5]
D0687
 
Fluvoxamine
 
C15H21F3N2O2
 
5324346 
Major    Inter Info   
[4], [5]
D0251
 
Capmatinib
 
C23H17FN6O
 
25145656 
Major    Inter Info   
[3], [4], [5]
D0724
 
Givosiran
 
C78H139N11O30
 
119058042 
Major    Inter Info   
[3], [4], [5]
D1189
 
Osilodrostat
 
C13H10FN3
 
44139752 
Major    Inter Info   
[3], [4], [5]
D1432
 
Rucaparib
 
C19H18FN3O
 
9931954 
Major    Inter Info   
[3], [4], [5]
D1687
 
Vemurafenib
 
C23H18ClF2N3O3S
 
42611257 
Major    Inter Info   
[3], [4], [5]
D0084
 
Anagrelide
 
C10H7Cl2N3O
 
135409400 
Moderate    Inter Info   
[4], [5]
D0220
 
Bupropion
 
C13H18ClNO
 
444 
Moderate    Inter Info   
[4], [5], [24]
D0313
 
Chloramphenicol
 
C11H12Cl2N2O5
 
5959 
Moderate    Inter Info   
[4], [5], [24]
D0337
 
Cimetidine
 
C10H16N6S
 
2756 
Moderate    Inter Info   
[4], [5], [24]
D0338
 
Cinacalcet
 
C22H22F3N
 
156419 
Moderate    Inter Info   
[4], [5], [24]
D0432
 
Deferasirox
 
C21H15N3O4
 
214348 
Moderate    Inter Info   
[4], [5]
D0439
 
Delavirdine
 
C22H28N6O3S
 
5625 
Moderate    Inter Info   
[4], [5], [24]
D0509
 
Disulfiram
 
C10H20N2S4
 
3117 
Moderate    Inter Info   
[4], [5], [24]
D0534
 
Dronedarone
 
C31H44N2O5S
 
208898 
Moderate    Inter Info   
[4], [5], [24]
D0539
 
Duloxetine
 
C18H19NOS
 
60835 
Moderate    Inter Info   
[4], [5], [24]
D0603
 
Esomeprazole
 
C17H19N3O3S
 
9568614 
Moderate    Inter Info   
[4], [5], [24]
D0619
 
Ethinylestradiol
 
C20H24O2
 
5991 
Moderate    Inter Info   
[4], [5]
D0642
 
Fenofibrate
 
C20H21ClO4
 
3339 
Moderate    Inter Info   
[4], [5], [24]
D0667
 
Fluconazole
 
C13H12F2N6O
 
3365 
Moderate    Inter Info   
[4], [5], [24]
D0676
 
Fluoxetine
 
C17H18F3NO
 
3386 
Moderate    Inter Info   
[4], [5], [24]
D0678
 
Fluphenazine
 
C22H26F3N3OS
 
3372 
Moderate    Inter Info   
[4], [5], [24]
D0715
 
Gemfibrozil
 
C15H22O3
 
3463 
Moderate    Inter Info   
[4], [5], [24]
D0793
 
Imatinib
 
C29H31N7O
 
5291 
Moderate    Inter Info   
[4], [5], [24]
D0858
 
Isoniazid
 
C6H7N3O
 
3767 
Moderate    Inter Info   
[4], [5], [24]
D0892
 
Lansoprazole
 
C16H14F3N3O2S
 
3883 
Moderate    Inter Info   
[4], [5], [24]
D0907
 
Letrozole
 
C17H11N5
 
3902 
Moderate    Inter Info   
[4], [5], [24]
D1026
 
Methotrimeprazine
 
C19H24N2OS
 
72287 
Moderate    Inter Info   
[4], [5], [24]
D1028
 
Methoxsalen
 
C12H8O4
 
4114 
Moderate    Inter Info   
[4], [5]
D1054
 
Mexiletine
 
C11H17NO
 
4178 
Moderate    Inter Info   
[4], [5]
D1057
 
Miconazole
 
C18H14Cl4N2O
 
4189 
Moderate    Inter Info   
[4], [5], [24]
D1063
 
Mifepristone
 
C29H35NO2
 
55245 
Moderate    Inter Info   
[4], [5], [24]
D1143
 
Nitisinone
 
C14H10F3NO5
 
115355 
Moderate    Inter Info   
[4], [5], [24]
D1179
 
Omeprazole
 
C17H19N3O3S
 
4594 
Moderate    Inter Info   
[4], [5], [24]
D1195
 
Oxandrolone
 
C19H30O3
 
5878 
Moderate    Inter Info   
[4], [5], [24]
D1198
 
Oxcarbazepine
 
C15H12N2O2
 
34312 
Moderate    Inter Info   
[4], [5], [24]
D1229
 
Paroxetine
 
C19H20FNO3
 
43815 
Moderate    Inter Info   
[4], [5], [24]
D0002
 
Abametapir (topical)
 
C12H12N2
 
15664 
Moderate    Inter Info   
[34]
D0007
 
Abiraterone
 
C24H31NO
 
132971 
Moderate    Inter Info   
[4], [5], [24]
D0171
 
Berotralstat
 
C30H26F4N6O
 
137528262 
Moderate    Inter Info   
[36]
D0300
 
Cenobamate
 
C10H10ClN5O2
 
11962412 
Moderate    Inter Info   
[4], [5], [24]
D0302
 
Ceritinib
 
C28H36ClN5O3S
 
57379345 
Moderate    Inter Info   
[3], [4], [39]
D0409
 
Dacomitinib
 
C24H25ClFN5O2
 
11511120 
Moderate    Inter Info   
[4], [5], [24]
D0559
 
Eliglustat
 
C23H36N2O4
 
23652731 
Moderate    Inter Info   
[4], [5], [24]
D0601
 
Eslicarbazepine
 
C15H14N2O2
 
9881504 
Moderate    Inter Info   
[4], [5], [24]
D0628
 
Etravirine
 
C20H15BrN6O
 
193962 
Moderate    Inter Info   
[4], [5], [24]
D0638
 
Fedratinib
 
C27H36N6O3S
 
16722836 
Moderate    Inter Info   
[4], [5], [24]
D0732
 
Glycerol phenylbutyrate
 
C33H38O6
 
10482134 
Moderate    Inter Info   
[4], [40]
D0869
 
Ivacaftor
 
C24H28N2O3
 
16220172 
Moderate    Inter Info   
[42], [43], [44], [45]
D0946
 
Lonafarnib
 
C27H31Br2ClN4O2
 
148195 
Moderate    Inter Info   
[4], [5], [24]
D0960
 
Lumefantrine
 
C30H32Cl3NO
 
6437380 
Moderate    Inter Info   
[4], [5], [48]
D1074
 
Mirabegron
 
C21H24N4O2S
 
9865528 
Moderate    Inter Info   
[4], [5], [24]
D1160
 
Obeticholic acid
 
C26H44O4
 
447715 
Moderate    Inter Info   
[4], [5]
D1221
 
Panobinostat
 
C21H23N3O2
 
6918837 
Moderate    Inter Info   
[4], [5], [24]
D1423
 
Rolapitant
 
C25H26F6N2O2
 
10311306 
Moderate    Inter Info   
[4], [5], [24]
D1505
 
Stiripentol
 
C14H18O3
 
5311454 
Moderate    Inter Info   
[4], [5], [24]
D1339
 
Primaquine
 
C15H21N3O
 
4908 
Moderate    Inter Info   
[4], [5]
D1371
 
Quinidine
 
C20H24N2O2
 
441074 
Moderate    Inter Info   
[4], [5], [24]
D1383
 
Ranolazine
 
C24H33N3O4
 
56959 
Moderate    Inter Info   
[4], [5], [24]
D1461
 
Sertraline
 
C17H17Cl2N
 
68617 
Moderate    Inter Info   
[4], [5], [24]
D1553
 
Terbinafine
 
C21H25N
 
1549008 
Moderate    Inter Info   
[4], [5], [24]
D1571
 
Thiabendazole
 
C10H7N3S
 
5430 
Moderate    Inter Info   
[4], [5]
D1581
 
Ticlopidine
 
C14H14ClNS
 
5472 
Moderate    Inter Info   
[4], [5]
D1706
 
Voriconazole
 
C16H14F3N5O
 
71616 
Moderate    Inter Info   
[4], [5], [24]
D1721
 
Zileuton
 
C11H12N2O2S
 
60490 
Moderate    Inter Info   
[4], [5]
D0193
 
Bortezomib
 
C19H25BN4O4
 
387447 
Minor    Inter Info   
[59]
   CYP450 enzyme induction Drug Num:  6
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0255
 
Carbamazepine
 
C15H12N2O
 
2554 
Moderate    Inter Info   
[4], [5]
D0697
 
Fosphenytoin
 
C16H15N2O6P
 
56339 
Moderate    Inter Info   
[4], [5]
D1283
 
Phenytoin
 
C15H12N2O2
 
1775 
Moderate    Inter Info   
[4], [5]
D0906
 
Letermovir
 
C29H28F4N4O4
 
45138674 
Moderate    Inter Info   
[46]
D0953
 
Lorlatinib
 
C21H19FN6O2
 
71731823 
Moderate    Inter Info   
[3], [4], [47]
D1400
 
Rifampicin
 
C43H58N4O12
 
135398735 
Moderate    Inter Info   
[4], [5]
      Pharmacodynamic additive effects
   Increased risk of hepatotoxicity Drug Num:  23
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0900
 
Leflunomide
 
C12H9F3N2O2
 
3899 
Major    Inter Info   
[6], [7], [8]
D0944
 
Lomitapide
 
C39H37F6N3O2
 
9853053 
Major    Inter Info   
[9]
D1073
 
Mipomersen
 
C230H324N67O122P19S19
 
118984467 
Major    Inter Info   
[10]
D1258
 
Pexidartinib
 
C20H15ClF3N5
 
25151352 
Major    Inter Info   
[11]
D1556
 
Teriflunomide
 
C12H9F3N2O2
 
54684141 
Major    Inter Info   
[6], [7], [8]
D0114
 
Asparaginase Escherichia coli
 
NA
 
NA
Moderate    Inter Info   
[13], [14], [15], [3], [4], [16], [17], [18], [19], [20], [21], [22], [23]
D0357
 
Clofarabine
 
C10H11ClFN5O3
 
119182 
Moderate    Inter Info   
[25]
D0554
 
Efavirenz
 
C14H9ClF3NO2
 
64139 
Moderate    Inter Info   
[26], [27]
D0826
 
Interferon beta-1a
 
NA
 
NA
Moderate    Inter Info   
[28], [29], [30], [31]
D0827
 
Interferon beta-1b
 
NA
 
NA
Moderate    Inter Info   
[28], [29], [30], [31]
D1025
 
Methotrexate
 
C20H22N8O5
 
126941 
Moderate    Inter Info   
[4], [32]
D1106
 
Naltrexone
 
C20H23NO4
 
5360515 
Moderate    Inter Info   
[33]
D1234
 
Pegaspargase
 
C14H19NO
 
436058 
Moderate    Inter Info   
[13], [14], [15], [3], [4], [16], [17], [18], [19], [20], [21], [22], [23]
D0113
 
Asparaginase Erwinia chrysanthemi
 
NA
 
NA
Moderate    Inter Info   
[13], [14], [15], [3], [4], [16], [17], [18], [19], [20], [21], [22], [23]
D0149
 
Bedaquiline
 
C32H31BrN2O2
 
5388906 
Moderate    Inter Info   
[35]
D0199
 
Brentuximab vedotin
 
NA
 
NA
Moderate    Inter Info   
[37]
D0232
 
Calaspargase pegol
 
NA
 
NA
Moderate    Inter Info   
[13], [14], [15], [3], [4], [16], [17], [18], [19], [20], [21], [22], [23]
D0248
 
Cannabidiol
 
C21H30O2
 
644019 
Moderate    Inter Info   
[4], [38]
D0789
 
Idelalisib
 
C22H18FN7O
 
11625818 
Moderate    Inter Info   
[41]
D1239
 
Peginterferon beta-1a
 
NA
 
NA
Moderate    Inter Info   
[28], [29], [30], [31]
D1389
 
Remdesivir
 
C27H35N6O8P
 
121304016 
Moderate    Inter Info   
[3], [4], [49], [50], [51]
D1615
 
Trabectedin
 
C39H43N3O11S
 
108150 
Moderate    Inter Info   
[4], [52]
D1589
 
Tioguanine
 
C5H5N5S
 
2723601 
Moderate    Inter Info   
[55], [56]
   Increased risk of photosensitivity reactions Drug Num:  5
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0062
 
Aminolevulinic acid
 
C5H9NO3
 
137 
Major    Inter Info   
[1], [2]
D0063
 
Aminolevulinic acid (topical)
 
C5H9NO3
 
137 
Moderate    Inter Info   
[3], [4], [12]
D1033
 
Methyl aminolevulinate (topical)
 
C6H11NO3
 
157922 
Moderate    Inter Info   
[3], [4], [12]
D1314
 
Porfimer sodium
 
C68H74N8O11
 
135577896 
Moderate    Inter Info   
[53], [4], [54]
D1691
 
Verteporfin
 
C82H84N8O16
 
11980904 
Moderate    Inter Info   
[4], [57], [1], [58]
References
1 Product Information. Nulibry (fosdenopterin). Origin Biosciences Inc, Boston, MA.
2 Product Information. Gleolan (aminolevulinic acid). NX Development Corp, Lexington, KY.
3 Cerner Multum, Inc. "Australian Product Information.".
4 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
5 Product Information. Esbriet (pirfenidone). Intermune Inc, Brisbane, CA.
6 Canadian Pharmacists Association.
7 EMEA "EMEA public statement on leflunomide (ARAVA) - severe and serious hepatic reactions.".
8 Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
9 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
10 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
11 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
12 Product Information. Metvixia (methyl aminolevulinate topical). Galderma Laboratories Inc, Cranbury, NJ.
13 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]
14 Bodmer M, Sulz M, Stadlmann S, Droll A, Terracciano L, Krahenbuhl S "Fatal liver failure in an adult patient with acute lymphoblastic leukemia following treatment with L-asparaginase." Digestion 74 (2006): epub. [PMID: 16988508]
15 Cerner Multum, Inc "ANVISA Bulario Eletrnico.".
16 Christ TN, Stock W, Knoebel RW "Incidence of asparaginase-related hepatotoxicity, pancreatitis, and thrombotic events in adults with acute lymphoblastic leukemia treated with a pediatric-inspired regimen." J Oncol Pharm Pract 24 (2018): 299-308. [PMID: 28355969]
17 Jenkins R, Perlin E "Severe hepatotoxicity from Escherichia coli L-asparaginase." J Natl Med Assoc 79 (1987): 775-9. [PMID: 3305969]
18 Lu G, Karur V, Herrington JD, Walker MG "Successful treatment of pegaspargase-induced acute hepatotoxicity with vitamin B complex and L-carnitine" Proc (Bayl Univ Med Cent) 29 (2016): 46-7. [PMID: 26722167]
19 Product Information. Asparlas (calaspargase pegol). Servier, Boston, MA.
20 Product Information. Elspar (asparaginase). Merck & Co, Inc, West Point, PA.
21 Product Information. Erwinaze (asparaginase Erwinia chrysanthemi). EUSA Pharma, Newtown, PA.
22 Product Information. Oncaspar (pegaspargase). Rhone-Poulenc Rorer, Collegeville, PA.
23 Burke PW, Aldoss I, Lunning MA, et.al "High-grade PEGylated asparaginase-related hepatotoxicity occurrence in a pediatric-inspired adult acute lymphoblastic leukemia regimen does not necessarily predict recurrent hepatotoxicity in subsequent cycles." Blood 122 (2013): 2671. [PMID: 29407583]
24 Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
25 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
26 Elsharkawy AM, Schwab U, McCarron B, et al. "Efavirenz induced acute liver failure requiring liver transplantation in a slow drug metaboliser." J Clin Virol 58 (2013): 331-3. [PMID: 23763943]
27 Product Information. Sustiva (efavirenz). DuPont Pharmaceuticals, Wilmington, DE.
28 Product Information. Avonex (interferon beta-1a). Biogen, Cambridge, MA.
29 Product Information. Betaseron (interferon beta-1b). Berlex, Richmond, CA.
30 Product Information. Plegridy (peginterferon beta-1a). Biogen Idec Inc, Cambridge, MA.
31 Product Information. Rebif (interferon beta-1a). Serono Laboratories Inc, Norwell, MA.
32 Product Information. Methotrexate (methotrexate). Lederle Laboratories, Wayne, NJ.
33 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.
34 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
35 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
36 Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
37 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
38 Product Information. Epidiolex (cannabidiol). Greenwich Biosciences Inc, Carlsbad, CA.
39 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
40 Product Information. Ravicti (glycerol phenylbutyrate). Hyperion Therapeutics Inc, South San Francisco, CA.
41 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
42 Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
43 Product Information. Orkambi (ivacaftor-lumacaftor). Vertex Pharmaceuticals, Cambridge, MA.
44 Product Information. Symdeko 4-Week (ivacaftor-tezacaftor). Vertex Pharmaceuticals, Cambridge, MA.
45 Product Information. Trikafta (elexacaftor/ivacaftor/tezacaftor). Vertex Pharmaceuticals, Cambridge, MA.
46 Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
47 Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
48 Wohlt PD, Zheng L, Gunderson S, Balzar SA, Johnson BD, Fish JT "Recommendations for the use of medications with continuous enteral nutrition." Am J Health Syst Pharm 66 (2009): 1438-67. [PMID: 19667002]
49 European Medicines Agency "Summary on compassionate use. Remdesivir Gilead.".
50 Gilead Sciences, Inc "About Remdesivir.".
51 US Food and Drug Administration "Fact sheet for health care providers emergency use authorization (EUA) of remdesivir (GS-5734TM)".
52 Product Information. Yondelis (trabectedin). Janssen Pharmaceuticals, Titusville, NJ.
53 Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]
54 Product Information. Photofrin (porfimer). Sanofi Winthrop Pharmaceuticals, New York, NY.
55 Product Information. Aubagio (teriflunomide). Genzyme Corporation, Cambridge, MA.
56 Product Information. Tabloid (thioguanine). Prasco Laboratories, Cincinnati, OH.
57 Multum Information Services, Inc. Expert Review Panel.
58 Product Information. Visudyne (verteporfin) Valeant Pharmaceuticals, Costa Mesa, CA.
59 Product Information. Velcade (bortezomib). Millennium Pharmaceuticals Inc, Cambridge, MA.