Drug Details

General Information of the Drug (ID: DR3098)
Name
6-mercaptopurine
Synonyms
6-Mercaptopurine; mercaptopurine; 50-44-2; Purinethol; Mercapurin; 6-Thiopurine; Leukerin; Leupurin; Mercaleukin; 6-Thioxopurine; Puri-Nethol; Ismipur; 7H-purine-6-thiol; Mern; 6-Thiohypoxanthine; 6-Mercaptopurin; 6-Purinethiol; Purimethol; Purinethiol; 6-MP; 1,9-dihydro-6H-purine-6-thione; Purine-6-thiol; 3H-Purine-6-thiol; 6 MP; Mercaleukim; 9H-Purine-6-thiol; 1,7-Dihydro-6H-purine-6-thione; Hypoxanthine, thio-; Mercaptopurine (6-MP); 3,7-dihydropurine-6-thione; 6H-Purine-6-thione, 1,7-dihydro-; Mercaptopurin; Mercaptopurina; Mercaptopurinum; Merkaptopuryna; Xaluprine; 6-Merkaptopurin; Purine, 6-mercapto-; 9H-Purine-6(1H)-thione; Mercaptopurine anhydrous; Purine-6(1H)-thione; NCI-C04886; 7-Mercapto-1,3,4,6-tetrazaindene; 1H-Purine, 6-mercapto-; NSC 755; U-4748; NSC-755; UNII-PKK6MUZ20G; Mercaptopurine;6-MP; NSC755; 3,7-dihydro-6H-purine-6-thione; Purinethol (TN); PKK6MUZ20G; 1,9-dihydropurine-6-thione; 1H-purine-6(7H)-thione.; CHEBI:2208; 157930-13-7; Mercaptopurine (VAN); DSSTox_CID_810; Mercaptopurin [German]; Merkaptopuryna [Polish]; 6-Merkaptopurin [Czech]; DSSTox_RID_75801; DSSTox_GSID_20810; Mercaptopurine (anhydrous); 157930-14-8; Mercaptopurinum [INN-Latin]; Mercaptopurina [INN-Spanish]; Purixan; thiohypoxanthine; Purine-6-thiol, monohydrate; CAS-50-44-2; SMR000544948; Mercaptopurine, 6-; CCRIS 2761; Mercaptopurine (INN); HSDB 3235; SR-05000001925; 1194-62-3; EINECS 200-037-4; NCIMech_000025; 9H-Purin-6-yl hydrosulfide; a thiopurine; Mercaptopurine;; Mercaptopurine [USAN:USP:INN]; PubChem9680; Spectrum_000921; ACMC-1AUNA; Spectrum2_000060; Spectrum3_000491; Spectrum4_000857; Spectrum5_000950; M0063; H-Purine-6(1H)-thione; Azathioprine EP Impurity B; SCHEMBL3893; CHEMBL1425; BSPBio_001981; KBioGR_001493; KBioGR_002363; KBioSS_001401; KBioSS_002366; AG-670/31547064; MLS001066623; MLS001304020; MLS001304953; MLS006011869; ARONIS27054; DivK1c_000493; SPECTRUM1500387; SPBio_000219; GTPL7226; SCHEMBL2790086; 7H-Purin-6-yl hydrosulfide #; DTXSID0020810; SCHEMBL12683725; CHEBI:50667; CHEBI:94796; HMS501I15; KBio1_000493; KBio2_001401; KBio2_002363; KBio2_003969; KBio2_004931; KBio2_006537; KBio2_007499; KBio3_001481; KBio3_002842; 7-Mercapto-1,4,6-tetrazaindene; cMAP_000033; NINDS_000493; 6,7-dihydro-3H-purine-6-thione; HMS1920L07; HMS2091B20; HMS2236L06; HMS3259N03; HMS3369M05; HMS3651G07; HMS3713N10; HMS3747A17; HMS3872N13; Pharmakon1600-01500387; ACT11542; EBD16256; ZINC4658290; [S]C1=NC=NC2=C1NC=N2; Tox21_111158; Tox21_202591; 6450AJ; ANW-30999; ANW-57555; BBL033743; BDBM50423778; CCG-35344; CCG-39915; EBD540779; MFCD00233552; NSC759614; s1305; SBB037953; STK727062; STL257085; 6-Mercaptopurine, analytical standard; WLN: T56 BM DN FN HNJ ISH; AKOS000170222; AKOS000275858; AKOS005224624; AKOS008901311; AKOS016903205; Tox21_111158_1; AM81386; CCG-266232; CS-1499; DB01033; LS20858; MCULE-4811219863; NC00613; NSC-759614; IDI1_000493; NCGC00091641-02; NCGC00091641-03; NCGC00091641-04; NCGC00094717-01; NCGC00094717-02; NCGC00094717-03; NCGC00094717-05; NCGC00094717-06; NCGC00188973-01; NCGC00188973-02; NCGC00260139-01; AC-11464; AS-13109; H348; HY-13677; NCI60_041653; SMR004703503; ST086505; ST086506; SBI-0051437.P004; AB0013000; AB0119973; DB-026398; BB 0241023; FT-0621175; SW199090-2; EN300-61517; 1766-EP2270008A1; 1766-EP2272827A1; 1766-EP2272832A1; 1766-EP2277876A1; 1766-EP2292614A1; 1766-EP2292617A1; 1766-EP2295409A1; 1766-EP2295426A1; 1766-EP2295427A1; 1766-EP2298768A1; 1766-EP2298778A1; 1766-EP2308833A2; 1766-EP2308855A1; 1766-EP2308861A1; 1766-EP2314590A1; 1766-EP2316834A1; 1766-EP2374454A1; 50M442; C01756; C02380; D04931; W-5114; 15150-EP2272827A1; 15150-EP2275420A1; 15150-EP2295055A2; 15150-EP2295416A2; 15150-EP2298748A2; 15150-EP2298764A1; 15150-EP2298765A1; 15150-EP2305642A2; 15150-EP2305679A1; 15150-EP2308833A2; 15150-EP2311453A1; 15150-EP2311825A1; 15150-EP2311840A1; 15150-EP2311842A2; 15150-EP2316832A1; 15150-EP2316833A1; 21414-EP2270006A1; 21414-EP2270014A1; 21414-EP2272509A1; 21414-EP2272847A1; 21414-EP2275413A1; 21414-EP2277874A1; 21414-EP2284158A1; 21414-EP2287156A1; 21414-EP2287159A1; 21414-EP2295439A1; 21414-EP2311818A1; 21414-EP2314295A1; AB00171799_05; AB00641894-03; AB00641894-04; AB00641894_05; AB00876276-13; 233D552; 462M721; 599M524; A828129; Q418529; SR-05000001925-1; SR-05000001925-2; W-105961; purine antimetabolite: inhibits nucleic acid replication; 1,9-Dihydropurine-6-thione DISCONTINUED, see M225450; Mercaptopurine; 7H-Purine-6-thiol; Azathioprine BP Impurity B; 157930-11-5
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Molecular Type
Small molecule
Disease Mantle cell lymphoma [ICD-11: 2A85] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C5H4N4S
PubChem CID
667490
Canonical SMILES
C1=NC2=C(N1)C(=S)N=CN2
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
CAS Number
CAS 50-44-2
ChEBI ID
CHEBI:2208
TTD Drug ID
D09UZO
DrugBank ID
DB01033
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Bismuth (III)      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Decrease Cell proliferation capacity
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of Bi(III) with 6-MP endowed the newly developed amorphous [Bi(MP)3(NO3)2]NO3 with excellent anticancer activity against lung cancer cells and the solubility and bioavailability of the obtained [Bi(MP)3(NO3)2]NO3 were dramatically improved, compared with that of 6-MP.
Target and Pathway
Target(s) Amidophosphoribosyltransferase (PPAT)  Molecule Info  [3]
IMP dehydrogenase 1 (IMPDH1)  Molecule Info  [4]
BioCyc Purine nucleotides degradation Click to Show/Hide
2 Urate biosynthesis/inosine 5'-phosphate degradation
3 Guanosine nucleotides de novo biosynthesis
4 Superpathway of purine nucleotide salvage
5 Purine nucleotides de novo biosynthesis
6 Guanosine ribonucleotides de novo biosynthesis
KEGG Pathway Purine metabolism Click to Show/Hide
2 Drug metabolism - other enzymes
3 Metabolic pathways
Pathwhiz Pathway Purine Metabolism Click to Show/Hide
Reactome Purine ribonucleoside monophosphate biosynthesis Click to Show/Hide
WikiPathways Nucleotide Metabolism Click to Show/Hide
References
Reference 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).
Reference 2 Improvement in the Anticancer Activity of 6-Mercaptopurine via Combination with Bismuth(III). Chem Pharm Bull (Tokyo). 2016;64(11):1539-1545.
Reference 3 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.
Reference 4 Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67.
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