Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D09UZO
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| Former ID |
DAP000147
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| Drug Name |
Mercaptopurine
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| Synonyms |
6-mercaptopurine; Ismipur; Leukerin; Leupurin; Mercaleukim; Mercaleukin; Mercaptopurin; Mercaptopurina; Mercaptopurinum; Mercapurin; Merkaptopuryna; Mern; Purimethol; Purinethiol; Purinethol; Thiopurine; Leupu rin; Mercaptopurin [German]; Mercaptopurina Wellcome; Mercaptopurine anhydrous; Merkaptopuryna [Polish]; Puri Nethol; BW 57 323H; Glaxo Wellcome Brand of 6 Mercaptopurine; GlaxoSmithKline Brand of 6 Mercaptopurine; M0063; NCIMech_000025; PM6; Wellcome Brand of 6 Mercaptopurine; Glaxo Wellcome Brand of 6-Mercaptopurine; GlaxoSmithKline Brand of 6-Mercaptopurine; Mercaptopurina [INN-Spanish]; Mercaptopurine (INN); Mercaptopurine (VAN); Mercaptopurine (anhydrous); Mercaptopurinum [INN-Latin]; Puri-Nethol; Purineantimetabolite: inhibits nucleic acid replication; Purinethol (TN); U-4748; Wellcome Brand of 6-Mercaptopurine; AG-670/31547064; Purine-6-thiol; Leukerin, 99%-Carc; Purine-6(1H)-thione; Purinethol, 6-mercaptopurine, 6-MP, Mercaptopurine; 6 MP; 6 Mercaptopurine Monohydrate; 6 Thiohypoxanthine; 6 Thiopurine; 6-MERCAPTOPURINE MONOHYDRATE; 6-MP; 6-Mercaptopurin; 6-Merkaptopurin; 6-Merkaptopurin [Czech]; 6-Purinethiol; 6-Thiohypoxanthine; 6-Thiopurine; 6-Thioxopurine; Mercaptopurine (Purine analog)
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| Drug Type |
Small molecular drug
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| Indication | Acute lymphoblastic leukaemia [ICD-11: 2A85; ICD-10: C85.1, C88.7] | Approved | [1], [2] | |
| Crohn disease [ICD-11: DD70; ICD-10: K50, K50.9; ICD-9: 555] | Phase 4 | [3] | ||
| Therapeutic Class |
Anticancer Agents
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| Company |
Novopharm
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| Structure |
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Download2D MOL |
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| Formula |
C5H4N4S
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| Canonical SMILES |
C1=NC2=C(N1)C(=S)N=CN2
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| InChI |
1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
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| InChIKey |
GLVAUDGFNGKCSF-UHFFFAOYSA-N
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| CAS Number |
CAS 50-44-2
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| PubChem Compound ID | ||||
| PubChem Substance ID |
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
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| ChEBI ID |
CHEBI:2208
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| ADReCS Drug ID | BADD_D01392 | |||
| SuperDrug ATC ID |
L01BB02
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| SuperDrug CAS ID |
cas=000050442
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Prevotella copri
Show/Hide Hierarchy
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[4] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Prevotella copri was decreased by Mercaptopurine (adjusted p-values: 2.15E-04). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Collinsella aerofaciens
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[4] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Mercaptopurine (adjusted p-values: 2.09E-03). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Clostridioides difficile
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|
[4] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridioides difficile was decreased by Mercaptopurine (adjusted p-values: 2.08E-05). | |||
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Studied Microbe: Coprococcus comes
Show/Hide Hierarchy
|
[4] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by Mercaptopurine (adjusted p-values: 3.55E-04). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Amidophosphoribosyltransferase (PPAT) | Target Info | Breaker | [5] |
| Inosine-5'-monophosphate dehydrogenase 1 (IMPDH1) | Target Info | Inhibitor | [6] | |
| BioCyc | Purine nucleotides degradation | |||
| Urate biosynthesis/inosine 5'-phosphate degradation | ||||
| Guanosine nucleotides de novo biosynthesis | ||||
| Superpathway of purine nucleotide salvage | ||||
| Purine nucleotides de novo biosynthesis | ||||
| Guanosine ribonucleotides de novo biosynthesis | ||||
| KEGG Pathway | Purine metabolism | |||
| Drug metabolism - other enzymes | ||||
| Metabolic pathways | ||||
| Pathwhiz Pathway | Purine Metabolism | |||
| Reactome | Purine ribonucleoside monophosphate biosynthesis | |||
| WikiPathways | Nucleotide Metabolism | |||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7226). | |||
| REF 2 | S-adenosylmethionine regulates thiopurine methyltransferase activity and decreases 6-mercaptopurine cytotoxicity in MOLT lymphoblasts. Biochem Pharmacol. 2009 Jun 15;77(12):1845-53. | |||
| REF 3 | ClinicalTrials.gov (NCT00846703) The GD-2008 ALL Protocol for Childhood Acute Lymphoblastic Leukemia. U.S. National Institutes of Health. | |||
| REF 4 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 5 | 6-mercaptopurine (6-MP) induces p53-mediated apoptosis of neural progenitor cells in the developing fetal rodent brain. Neurotoxicol Teratol. 2009 Jul-Aug;31(4):198-202. | |||
| REF 6 | Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67. | |||
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