Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00399)
Name
Mercaptopurine
Synonyms    Click to Show/Hide the Synonyms of This API
6-Mercaptopurine; mercaptopurine; 50-44-2; Purinethol; Mercapurin; 6-Thiopurine; Leukerin; Leupurin; Mercaleukin; 7H-purine-6-thiol; 6-Thioxopurine; Puri-Nethol; Ismipur; 6-Thiohypoxanthine; 6-Mercaptopurin; 6-Purinethiol; Purimethol; Purinethiol; 1,9-dihydro-6H-purine-6-thione; Purine-6-thiol; 3H-Purine-6-thiol; Mercaleukim; 3,7-dihydropurine-6-thione; 9H-Purine-6-thiol; 1,7-Dihydro-6H-purine-6-thione; Hypoxanthine, thio-; Mercaptopurine (6-MP); 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; 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; CID 4071; 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; 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; 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
Clinical Status
Approved
Disease Indication Acute lymphoblastic leukemia ICD-11: 2B33 [1]
PubChem CID
667490
Formula
C5H4N4S
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=667490"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 152.18 Topological Polar Surface Area 85.2
XlogP 0 Complexity 190
Heavy Atom Count 10 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Mercaptopurine 50 mg tablet Click to Show/Hide the Full List of Formulation(s):          6 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Anhydrous lactose; Lactose monohydrate; Magnesium stearate; Hypromelloses; Sodium starch glycolate type a potato; Starch, corn; Starch, potato
                   Dosage Form Oral Tablet
                   Company RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Anhydrous lactose; Lactose monohydrate; Magnesium stearate; Hypromelloses; Sodium starch glycolate type a potato; Starch, corn; Starch, potato
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose; Magnesium stearate; Starch, corn; Starch, potato
                   Dosage Form Oral Tablet
                   Company Gate Pharmaceuticals; Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose monohydrate; Magnesium stearate; Starch, corn; Starch, potato
                   Dosage Form Oral Tablet
                   Company Quinn Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Stearic acid; Lactose; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Starch, corn
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved mercaptopurine from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.

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