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

General Information of Drug (ID: DR1255)
Drug Name
Pentoxifylline
Synonyms
Pentoxifilina; Pentoxifyllin; Pentoxifyllinum; Pentoxiphylline; Pentoxiphyllium; Pentoxyfilline; Pentoxyfylline; Pentoxyphyllin; Pentoxyphylline; Rentylin; Torental; Trental; Vazofirin; pentoxifylline; 1-(5-Oxohexyl)theobromine; Azupentat; BL 191; BL-191; Dimethyloxohexylxanthine; Durapental; Oxpentifylline; 3,7-Dihydro-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6-dione; 3,7-Dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione; 3,7-Dimethyl-1-(5-oxohexyl)xanthine
Indication Arteriosclerosis obliterans [ICD11: BD40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 278.31 Topological Polar Surface Area 75.5
Heavy Atom Count 20 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4740
PubChem SID
9628 ; 498489 ; 597360 ; 857899 ; 1916632 ; 3153146 ; 7703125 ; 7847567 ; 7889976 ; 8026211 ; 8150006 ; 8152909 ; 10321577 ; 10531727 ; 10589689 ; 11111613 ; 11111614 ; 11335904 ; 11361143 ; 11364338 ; 11366900 ; 11369462 ; 11373038 ; 11374032 ; 11377624 ; 11462115 ; 11466224 ; 11467344 ; 11484957 ; 11485808 ; 11488997 ; 11491635 ; 11492042 ; 11495258 ; 14799544 ; 17405494 ; 25623640 ; 26538474 ; 26612497 ; 26679957 ; 26719692 ; 26747196 ; 26747197 ; 26759331 ; 29223826 ; 46386861 ; 46393770 ; 46505940 ; 46511426 ; 47216797
ChEBI ID
CHEBI:7986
CAS Number
6493-05-6
TTD Drug ID
D09QEI
Formula
C13H18N4O3
Canonical SMILES
CC(=O)CCCCN1C(=O)C2=C(N=CN2C)N(C1=O)C
InChI
1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3
InChIKey
BYPFEZZEUUWMEJ-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
Lisofylline DM001196
501254
Oxidation - Oxidation 1 [3]
Lisofylline DM001196
501254
Reduction - Reduction 1 [4]
Pentoxifylline metabolite (S) M1 DM001200
23519621
Reduction - Reduction 1 [4] , [3]
Pentoxifylline metabolite M5 DM001202
3082496
Oxidation - Oxidation 1 [3]
Pentoxifylline metabolite M6 DM001203
15023898
Oxidation - Demethylation 1 [5]
Pentoxifylline metabolite M2 DM001199
15895955
Oxidation - Hydroxylation 2 [4]
Pentoxifylline metabolite M3 DM001198
18466971
Oxidation - Hydroxylation 2 [4]
Pentoxifylline metabolite M7 DM001197
15023893
Oxidation - Demethylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001981 Pentoxifylline Lisofylline Reduction - Reduction Unclear [4]
MR001982 Pentoxifylline Pentoxifylline metabolite (S) M1 Reduction - Reduction Unclear [4], [3]
MR001983 Pentoxifylline Pentoxifylline metabolite M5 Oxidation - Oxidation Unclear [3]
MR001984 Pentoxifylline Pentoxifylline metabolite M6 Oxidation - Demethylation CYP1A2 [5]
MR001978 Lisofylline Pentoxifylline metabolite M7 Oxidation - Demethylation CYP1A2 [4]
MR001979 Lisofylline Pentoxifylline metabolite M3 Oxidation - Hydroxylation Unclear [4]
MR001980 Lisofylline Pentoxifylline metabolite M2 Oxidation - Hydroxylation Unclear [4]
⏷ Show the Full List of 7 MR(s)
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 Pentoxifylline was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P450 isozymes involved in lisofylline metabolism to pentoxifylline in human liver microsomes. Drug Metab Dispos. 1997 Dec;25(12):1354-8.
3 Stereoselective metabolism of pentoxifylline in vitro and in vivo in humans Chirality. 2002 Aug;14(8):643-52. doi: 10.1002/chir.10121.
4 Metabolism of lisofylline and pentoxifylline in human liver microsomes and cytosol Drug Metab Dispos. 1996 Nov;24(11):1174-9.
5 Role of CYP1A2 and CYP2E1 in the pentoxifylline ciprofloxacin drug interaction Biochem Pharmacol. 2004 Jul 15;68(2):395-402. doi: 10.1016/j.bcp.2004.03.035.

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