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

General Information of Drug (ID: DR1719)
Drug Name
Xanthine
Synonyms
Isoxanthine; Pseudoxanthine; Purine-2(3H),6(1H)-dione; Purine-2,6-(1H,3H)-dione; Purine-2,6-diol; USAF CB-17; Xanthic oxide; Xanthin; xanthine; 1H-Purine-2,6(3H,7H)-dione; 1H-Purine-2,6-diol; 1H-Purine-2,6-dione, 3,7-dihydro-; 1H-Purine-2,6-dione, 3,9-dihydro-; 2,6(1,3)-Purinedion; 2,6-Dihydroxypurine; 2,6-Dioxo-1,2,3,6-tetrahydropurine; 2,6-dioxopurine; 3,7-Dihydro-1H-purine-2,6-dione; 3,7-dihydropurine-2,6-dione; 3,9-dihydro-1H-purine-2,6-dione; 69-89-6; 9H-Purine-2,6-(1H,3H)-dione; 9H-Purine-2,6-diol; 9H-xanthine; XAN
Indication Obstructive sleep apnea [ICD11: 7A41] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 152.11 Topological Polar Surface Area 86.9
Heavy Atom Count 11 Rotatable Bond Count 0
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
1188
PubChem SID
3286 ; 3675 ; 540766 ; 618939 ; 640647 ; 819059 ; 855329 ; 3135149 ; 3293457 ; 5455854 ; 6505008 ; 6533214 ; 7891115 ; 8144038 ; 8151018 ; 10533229 ; 11536787 ; 15120174 ; 15946662 ; 16142320 ; 16275634 ; 21317893 ; 24439533 ; 24771321 ; 24902122 ; 24902144 ; 24902156 ; 26683877 ; 26757757 ; 26988539 ; 31462592 ; 37613684 ; 38552853 ; 46507575 ; 47178680 ; 48036254 ; 48111548 ; 49658808 ; 49737749 ; 49748678 ; 50063430 ; 56435543 ; 56465164 ; 57320802 ; 58686048 ; 76273918 ; 81041251 ; 81054343 ; 85090415 ; 85164959
ChEBI ID
ChEBI:17712
CAS Number
69-89-6
TTD Drug ID
D0M3IN
Formula
C5H4N4O2
Canonical SMILES
C1=NC2=C(N1)C(=O)NC(=O)N2
InChI
1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
InChIKey
LRFVTYWOQMYALW-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
Guanine DM003593
135398634
Unclear 1 [4]
Uric acid DM000021
1175
Unclear 1 [6] , [2]
XMP DM003584
73323
Unclear 1 [2]
Allantoin DM003590
204
Unclear 2 [2]
GMP DM003585
135398631
Unclear 2 [2]
Allantoic acid DM003591
203
Unclear 3 [2]
GTP DM003588
135398633
Unclear 3 [2]
IMP DM001534
135398640
Unclear 3 [2]
SAMP DM003587
7156993
Unclear 4 [2]
Urea DM001344
1176
Unclear 4 [2]
Adenosine Phosphate DM000018
6083
Unclear 5 [2]
CO2 DM000908
280
Unclear 5 [2]
NH3 DM003052
222
Unclear 5 [2]
ATP DM000020
5957
Unclear 6 [2]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004024 Xanthine XMP Unclear xpt [2]
MR004031 Xanthine Uric acid Unclear XDH [6], [2]
MR004037 Xanthine Guanine Unclear GDA [4]
MR004032 Uric acid Allantoin Unclear Unclear [2]
MR004025 XMP GMP Unclear guaA [2]
MR004033 Allantoin Allantoic acid Unclear Unclear [2]
MR004026 GMP IMP Unclear guaC [2]
MR004030 GMP GTP Unclear Unclear [2]
MR004034 Allantoic acid Urea Unclear Unclear [2]
MR004027 IMP SAMP Unclear purA [2]
MR004028 SAMP AMP Unclear purB [2]
MR004035 Urea NH3 Unclear Unclear [2]
MR004036 Urea Carbon dioxide Unclear Unclear [2]
MR004029 AMP ATP Unclear Unclear [2]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenylosuccinate lyase (purB) DMEN140 Bacillus subtilis
PUR8_BACSU
4.3.2.2
[2]
Adenylosuccinate synthetase (purA) DMEN139 Bacillus subtilis
PURA_BACSU
6.3.4.4
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
GMP reductase (guaC) DMEN138 Bacillus subtilis
GUAC_BACSU
1.7.1.7
[2]
GMP synthase [glutamine-hydrolyzing] (guaA) DMEN137 Bacillus subtilis
GUAA_BACSU
6.3.5.2
[2]
Guanine deaminase (GDA) DMEN141 Homo sapiens
GUAD_HUMAN
3.5.4.3
[4]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[5]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[6] , [2]
Xanthine phosphoribosyltransferase (xpt) DMEN136 Bacillus subtilis
XPT_BACSU
2.4.2.22
[2]
⏷ Show the Full List of 9  DME(s)
References
1 Febuxostat (TMX-67), a novel, non-purine, selective inhibitor of xanthine oxidase, is safe and decreases serum urate in healthy volunteers. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1111-6.
2 Xanthine metabolism in Bacillus subtilis: characterization of the xpt-pbuX operon and evidence for purine- and nitrogen-controlled expression of genes involved in xanthine salvage and catabolism
3 Rapid determination of five probe drugs and their metabolites in human plasma and urine by liquid chromatography/tandem mass spectrometry: application to cytochrome P450 phenotyping studies. Rapid Commun Mass Spectrom. 2004;18(23):2921-33.
4 Biosensing methods for xanthine determination: a review
5 Molecular characterization and taurine regulation of two novel CDOs (CDO1 and CDO2) from Carassius auratus. Comp Biochem Physiol B Biochem Mol Biol. 2019 Sep;235:54-61.
6 Xanthine oxidoreductase activity is correlated with hepatic steatosis

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