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

General Information of Drug (ID: DR1031)
Drug Name
Mercaptopurine
Synonyms
Mercaleukim; Mercaleukin; Mercaptopurin; Mercaptopurina; Mercaptopurine (6-MP); Mercaptopurinum; Mercapurin; Merkaptopuryna; Puri-Nethol; Purimethol; Purine-6-thiol; Purinethiol; Purinethol; mercaptopurine; 1,7-Dihydro-6H-purine-6-thione; Hypoxanthine, thio-; Ismipur; Leukerin; Leupurin; 1,9-dihydro-6H-purine-6-thione; 3,7-dihydropurine-6-thione; 3H-Purine-6-thiol; 50-44-2; 6 MP; 6-MP; 6-Mercaptopurin; 6-Mercaptopurine; 6-Purinethiol; 6-Thiohypoxanthine; 6-Thiopurine; 6-Thioxopurine; 7H-purine-6-thiol; 9H-Purine-6-thiol; Mern
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 152.18 Topological Polar Surface Area 85.2
Heavy Atom Count 10 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
667490
PubChem SID
4889 ; 5422 ; 538245 ; 602747 ; 3205553 ; 4912489 ; 5334583 ; 5370645 ; 6477910 ; 7366114 ; 7979906 ; 8136889 ; 8148223 ; 8149413 ; 9276666 ; 11335668 ; 11360907 ; 11363815 ; 11364775 ; 11366377 ; 11367337 ; 11368939 ; 11369899 ; 11371581 ; 11372939 ; 11374631 ; 11375499 ; 11377101 ; 11378064 ; 11446005 ; 11446674 ; 11461879 ; 11483955 ; 11487876 ; 11490307 ; 11492672 ; 11494735 ; 14772317 ; 15321640 ; 15970891 ; 16997018 ; 24882910 ; 25622685 ; 26611807 ; 26679290 ; 26748122 ; 26748123 ; 26748124 ; 31299583 ; 31665082
ChEBI ID
ChEBI:50667
CAS Number
50-44-2
TTD Drug ID
D09UZO
Formula
C5H4N4S
Canonical SMILES
CCC1C(COC1=O)CC2=CN=CN2C.[N+](=O)(O)[O-]
InChI
1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChIKey
GLVAUDGFNGKCSF-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
6-methylmercaptopurine DM014884
5778
Unclear - Unclear 1 [3] , [5]
6-thioinosine monophosphate DM015426
5184161
Unclear - Unclear 1 [3] , [5]
Thiouric acid DM015386
3032417
Unclear - Unclear 1 [3] , [5]
6-methylthioinosine monophosphate DM015281
437075
Unclear - Unclear 2 [3] , [5]
6-thioinosine triphosphate pyrophosphate DM018105 N. A. Unclear - Unclear 2 [3] , [5]
6-thioxanthosine monophosphate DM018104 N. A. Unclear - Unclear 2 [3] , [5]
6-methyl thioinosine triphosphate pyrophosphate DM018106 N. A. Unclear - Unclear 3 [3] , [5]
6-thioguanine nucleotides DM018064 N. A. Unclear - Unclear 3 [3] , [5]
6-thioguanine monophosphate DM015419
4269332
Unclear - Unclear 4 [3] , [5]
6-thioguanine diphosphate DM015414
3487004
Unclear - Unclear 5 [3] , [5]
6-thioguanine triphosphate DM015526
9807279
Unclear - Unclear 6 [3] , [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009972 Mercaptopurine 6-thioinosine monophosphate Unclear - Unclear HPRT1 [3], [5]
MR009981 Mercaptopurine 6-methylmercaptopurine Unclear - Unclear TPMT [3], [5]
MR009982 Mercaptopurine 6-thiouric acid Unclear - Unclear XDH [3], [5]
MR009973 6-thioinosine monophosphate 6-thioxanthosine monophosphate Unclear - Unclear IMPDH [3], [5]
MR009978 6-thioinosine monophosphate 6-thioinosine triphosphate pyrophosphate Unclear - Unclear Unclear [3], [5]
MR009980 6-thioinosine monophosphate 6-methylthioinosine monophosphate Unclear - Unclear TPMT [3], [5]
MR009979 6-thioinosine triphosphate pyrophosphate 6-methyl thioinosine triphosphate pyrophosphate Unclear - Unclear TPMT [3], [5]
MR009974 6-thioxanthosine monophosphate 6-thioguanine nucleotides Unclear - Unclear GMPS [3], [5]
MR009975 6-thioguanine nucleotides 6-thioguanine monophosphate Unclear - Unclear Unclear [3], [5]
MR009976 6-thioguanine monophosphate 6-thioguanine diphosphate Unclear - Unclear MPK [3], [5]
MR009977 6-thioguanine diphosphate 6-thioguanine triphosphate Unclear - Unclear Unclear [3], [5]
⏷ Show the Full List of 11 MR(s)
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]
Glutamine amidotransferase (GMPS) DME0159 Homo sapiens
GUAA_HUMAN
6.3.5.2
[3]
Thiopurine methyltransferase (TPMT) DME0014 Homo sapiens
TPMT_HUMAN
2.1.1.67
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
References
1 Mercaptopurine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62.
3 Azathioprine and 6-mercaptopurine pharmacogenetics and metabolite monitoring in inflammatory bowel disease
4 The degree of myelosuppression during maintenance therapy of adolescents with B-lineage intermediate risk acute lymphoblastic leukemia predicts risk of relapse. Leukemia. 2010 Apr;24(4):715-20.
5 6-Mercaptopurine metabolism in Crohn's disease: correlation with efficacy and toxicity

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