Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1299)
Drug Name
Pirfenidone
Synonyms
Pirespa; Pirfenidona; Pirfenidona [INN-Spanish]; Pirfenidone [USAN:INN]; Pirfenidonum; Pirfenidonum [INN-Latin]; 2(1H)-Pyridinone, 5-methyl-1-phenyl-; 5-Methyl-1-phenyl-1H-pyridin-2-one; 5-Methyl-1-phenyl-2(1H)-pyridone; 5-Methyl-1-phenyl-2-(1H)-pyridone; AMR 69; AMR-69; D7NLD2JX7U; Deskar; Esbriet; ISWRGOKTTBVCFA-UHFFFAOYSA-N; PIRFENIDONE; 5-methyl-1-phenyl-2(1H)-pyridinone; 5-methyl-1-phenyl-2-pyridinone; 5-methyl-1-phenylpyridin-2(1H)-one; 5-methyl-1-phenylpyridin-2-one; 53179-13-8; BRN 1526549; CHEBI:32016; UNII-D7NLD2JX7U
Indication Acute kidney failure [ICD11: GB60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 185.22 Topological Polar Surface Area 20.3
Heavy Atom Count 14 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
40632
PubChem SID
4550246 ; 7848646 ; 8176695 ; 11111619 ; 11113908 ; 11120277 ; 11120765 ; 11121253 ; 12012763 ; 14772813 ; 17405465 ; 24278625 ; 34706381 ; 46500438 ; 47291345 ; 50034790 ; 50104718 ; 50104719 ; 53778013 ; 53787735 ; 57312455 ; 58107008 ; 78277830 ; 85171290 ; 85231182 ; 85787591 ; 90341749 ; 91011848 ; 92304270 ; 92721958 ; 93578964 ; 102979948 ; 104334885 ; 118048538 ; 121361560 ; 123092043 ; 124750088 ; 124800846 ; 124881082 ; 124881083 ; 125307545 ; 125352326 ; 126618686 ; 126648858 ; 126667061 ; 128215666 ; 131317646 ; 131408321 ; 132556324 ; 134339376
ChEBI ID
CHEBI:32016
CAS Number
53179-13-8
TTD Drug ID
D02WCI
Formula
C12H11NO
Canonical SMILES
CC1=CN(C(=O)C=C1)C2=CC=CC=C2
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
5-hydroxy pirfenidone DM002866
11988811
Oxidation - 5-Hydroxylation 1 [3] , [4] , [5]
5-Carboxy pirfenidone DM002867
11988812
Oxidation - Oxidation 2 [3] , [4] , [5]
Acetoxypirfenidone DM002869 N. A. Unclear 2 [3] , [4] , [5]
Hydroxy pirfenidone glucuronide DM002868 N. A. Unclear 2 [3] , [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003332 Pirfenidone 5-hydroxy pirfenidone Oxidation - 5-Hydroxylation CYP1A2 [3], [4], [5]
MR003329 5-hydroxy pirfenidone 5-Carboxy pirfenidone Oxidation - Oxidation Unclear [3], [4], [5]
MR003330 5-hydroxy pirfenidone Hydroxy pirfenidone glucuronide Unclear Unclear [3], [4], [5]
MR003331 5-hydroxy pirfenidone Acetoxypirfenidone Unclear Unclear [3], [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
References
1 Pirfenidone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Pharmacokinetic evaluation of tissue distribution of pirfenidone and its metabolites for idiopathic pulmonary fibrosis therapy Biopharm Drug Dispos. 2015 May;36(4):205-15. doi: 10.1002/bdd.1932.
4 Pharmacokinetic and pharmacometabolomic study of pirfenidone in normal mouse tissues using high mass resolution MALDI-FTICR-mass spectrometry imaging Histochem Cell Biol. 2016 Feb;145(2):201-11. doi: 10.1007/s00418-015-1382-7.
5 Pharmacokinetics and metabolism of intravenous pirfenidone in sheep Biopharm Drug Dispos. 2008 Mar;29(2):119-26. doi: 10.1002/bdd.595.

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