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

General Information of Drug (ID: DR0066)
Drug Name
Allopurinol
Prodrug Info Allopurinol is the prodrug of Oxipurinol
Synonyms
Adenock; Ailural; Allopur; Allozym; Allural; Aloral; Alositol; Aluline; Anoprolin; Anzief; Apulonga; Apurin; Apurol; Atisuril; Bleminol; Bloxanth; Caplenal; Cellidrin; Cosuric; Dabrosin; Dabroson; Embarin; Epidropal; Foligan; Geapur; Gichtex; Hamarin; Hexanuret; Ketanrift; Ketobun-A; Ledopur; Lopurin; Lysuron; Milurit; Miniplanor; Monarch; Nektrohan; Progout; Riball; Suspendol; Takanarumin; Uricemil; Uriprim; Uripurinol; Urobenyl; Urolit; Urosin; Urtias; Xanturat; Zyloprim; Zyloric; allopurinol; 1H-Pyrazolo[3,4-d]pyrimidin-4-ol; 315-30-0; Gotax; Remid; Urbol
Indication Uncontrolled gout [ICD11: FA25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 136.11 Topological Polar Surface Area 70.1
Heavy Atom Count 10 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
135401907
ChEBI ID
CHEBI:40279
CAS Number
315-30-0
TTD Drug ID
D04KYY
Formula
C5H4N4O
Canonical SMILES
C1=NNC2=C1C(=O)NC=N2
InChI
1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
InChIKey
OFCNXPDARWKPPY-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
Allopurinol-1-riboside DM000048
135432358
Conjugation - Conjugation 1 [2]
Allopurinol-1-ribotide DM000047
168354693
Unclear 1 [2]
Oxipurinol DM000045
135398752
Oxidation - Oxidation 1 [4]
Allopurinol-1-riboside DM000048
135432358
Unclear 2 [2]
Oxipurinol-1-riboside DM000046 N. A. Conjugation - Conjugation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000139 Allopurinol Oxipurinol Oxidation - Oxidation XDH [4]
MR000140 Allopurinol Allopurinol-1-ribotide Unclear Unclear [2]
MR000141 Allopurinol Allopurinol-1-riboside Conjugation - Conjugation PNP [2]
MR000138 Allopurinol-1-ribotide Allopurinol-1-riboside Unclear HPRT1 [2]
MR000137 Oxipurinol Oxipurinol-1-riboside Conjugation - Conjugation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Hypoxanthine phosphoribosyltransferase (HPRT1) DME0223 Homo sapiens
HPRT_HUMAN
2.4.2.8
[2]
Purine nucleoside phosphorylase (PNP) DME0437 Homo sapiens
PNPH_HUMAN
2.4.2.1
[2]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[3]
Xanthine dehydrogenase/oxidase (XDH) DME0070 Homo sapiens
XDH_HUMAN
1.17.1.4
[4]
References
1 Allopurinol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 On the metabolism of allopurinol. Formation of allopurinol-1-riboside in purine nucleoside phosphorylase deficiency Biochem Pharmacol. 1983 Jul 15;32(14):2167-74. doi: 10.1016/0006-2952(83)90222-8.
3 Xanthine oxidase inhibition by allopurinol affects the reliability of urinary caffeine metabolic ratios as markers for N-acetyltransferase 2 and CYP1A2 activities. Eur J Clin Pharmacol. 1999 Jan;54(11):869-76.
4 Clinical pharmacokinetics of allopurinol Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53. doi: 10.2165/00003088-198611050-00001.

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