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

General Information of Drug (ID: DR1575)
Drug Name
Theophylline
Synonyms
Teofyllamin; Teolair; Theacitin; Theo-dur; Theobid; Theocin; Theocontin; Theofol; Theograd; Theolair; Theolix; Theophyl-225; Theophyllin; Theophylline anhydrous; Theovent; Uniphyl; Uniphyllin; Xantivent; theophylline; 1,3-Dimethylxanthine; Acet-theocin; Aerolate; Aerolate III; Armophylline; Bronkodyl; Doraphyllin; Elixex; Elixicon; Elixophyllin; Elixophylline; Lanophyllin; Liquophylline; Maphylline; Medaphyllin; Nuelin; Optiphyllin; Parkophyllin; Pseudotheophylline; Respbid; Slo-bid; Slo-phyllin; Solosin; Sustaire; Synophylate; 58-55-9; Accurbron
Indication Chronic obstructive pulmonary disease [ICD11: CA22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 180.16 Topological Polar Surface Area 69.3
Heavy Atom Count 13 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2153
PubChem SID
9340 ; 68760 ; 603445 ; 855679 ; 3140219 ; 4657313 ; 5643002 ; 7847437 ; 7890742 ; 7980771 ; 8026207 ; 8144385 ; 8149549 ; 8151463 ; 10518342 ; 10528330 ; 10528902 ; 11335378 ; 11360617 ; 11363932 ; 11366494 ; 11369056 ; 11371683 ; 11373924 ; 11377218 ; 11406129 ; 11461589 ; 11466848 ; 11466901 ; 11467968 ; 11468021 ; 11484559 ; 11486376 ; 11486602 ; 11488658 ; 11490488 ; 11492168 ; 11494852 ; 11537637 ; 14772732 ; 17389715 ; 21317898 ; 22390364 ; 22391535 ; 24277677 ; 24900236 ; 24900474 ; 24900581 ; 26611941 ; 26679415
ChEBI ID
ChEBI:28177
CAS Number
58-55-9
TTD Drug ID
D0F8RA
Formula
C7H8N4O2
Canonical SMILES
CN1C2=C(C(=O)N(C1=O)C)NC=N2
InChI
1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChIKey
ZFXYFBGIUFBOJW-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
1,3-Dimethyluric acid DM001115
70346
Oxidation - 8-hydroxylation 1 [7]
1-Methylxanthine DM000521
80220
Oxidation - 3-N-demethylation 1 [7]
3-MX DM001116
70639
Oxidation - 1-N-demethylation 1 [7]
Caffeine DM004603
2519
Unclear 1 [8]
1-Methyluric acid DM000522
69726
Oxidation - Hydrolyzationn 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004944 Theophylline 1-Methylxanthine Oxidation - 3-N-demethylation CYP1A2 [7]
MR004946 Theophylline 3-methylxanthine Oxidation - 1-N-demethylation CYP1A2 [7]
MR004947 Theophylline 1,3-dimethyluric acid Oxidation - 8-hydroxylation CYP2E1 [7]
MR004948 Theophylline Caffeine Unclear Unclear [8]
MR004945 1-Methylxanthine 1-methyluric acid Oxidation - Hydrolyzationn XDH [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[7]
⏷ Show the Full List of 7  DME(s)
References
1 Theophylline was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7.
3 Association between common CYP1A2 polymorphisms and theophylline metabolism in non-smoking healthy volunteers. Basic Clin Pharmacol Toxicol. 2013 Apr;112(4):257-63.
4 Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22.
5 Characterization of human cytochromes P450 involved in theophylline 8-hydroxylation. Biochem Pharmacol. 1995 Jul 17;50(2):205-11.
6 Construction and assessment of models of CYP2E1: predictions of metabolism from docking, molecular dynamics, and density functional theoretical calculations. J Med Chem. 2003 Apr 24;46(9):1645-60.
7 Theophylline metabolism in human liver microsomes: inhibition studies. J Pharmacol Exp Ther. 1996 Mar;276(3):912-7.
8 Metabolism of theophylline to caffeine in human fetal liver

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