Drug Information

General Information
Drug ID
DR00145
Drug Name
Mercaptopurine
Synonyms
1,7-Dihydro-6H-purine-6-thione; 1,9-dihydro-6H-purine-6-thione; 3,7-dihydropurine-6-thione; 3H-Purine-6-thiol; 6 MP; 6 Mercaptopurine; 6 Mercaptopurine Monohydrate; 6 Thiohypoxanthine; 6 Thiopurine; 6-MERCAPTOPURINE MONOHYDRATE; 6-MP; 6-Mercaptopurin; 6-Mercaptopurine; 6-Merkaptopurin; 6-Merkaptopurin [Czech]; 6-Purinethiol; 6-Thiohypoxanthine; 6-Thiopurine; 6-Thioxopurine; 7-Mercapto-1,3,4,6-tetrazaindene; 7H-purine-6-thiol; 9H-Purin-6-yl hydrosulfide; 9H-Purine-6(1H)-thione; AG-670/31547064; BW 57 323H; Glaxo Wellcome Brand of 6 Mercaptopurine; Glaxo Wellcome Brand of 6-Mercaptopurine; GlaxoSmithKline Brand of 6 Mercaptopurine; GlaxoSmithKline Brand of 6-Mercaptopurine; Ismipur; Leukerin; Leukerin, 99%-Carc; Leupu rin; Leupurin; M0063; Mercaleukim; Mercaleukin; Mercaptopurin; Mercaptopurin [German]; Mercaptopurina; Mercaptopurina Wellcome; Mercaptopurina [INN-Spanish]; Mercaptopurine (INN); Mercaptopurine (Purine analog); Mercaptopurine (VAN); Mercaptopurine (anhydrous); Mercaptopurine anhydrous; Mercaptopurinum; Mercaptopurinum [INN-Latin]; Mercapurin; Merkaptopuryna; Merkaptopuryna [Polish]; Mern; NCIMech_000025; PM6; Puri Nethol; Puri-Nethol; Purimethol; Purine-6(1H)-thione; Purine-6-thiol; Purineantimetabolite: inhibits nucleic acid replication; Purinethiol; Purinethol; Purinethol (TN); Purinethol, 6-mercaptopurine, 6-MP, Mercaptopurine; Thiopurine; U-4748; Wellcome Brand of 6 Mercaptopurine; Wellcome Brand of 6-Mercaptopurine
Drug Type
Small molecular drug
Indication Acute lymphoblastic leukemia [ICD11:2B33.0] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C5H4N4S
Canonical SMILES
C1=NC2=C(N1)C(=S)N=CN2
InChI
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
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
XLogP
0
PubChem CID
667490
PubChem SID
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 ,3205553 ,4889 ,4912489 ,5334583 ,5370645 ,538245 ,5422 ,602747 ,6477910 ,7366114 ,7979906 ,8136889 ,8148223 ,8149413 ,9276666
ChEBI ID
ChEBI:50667
TTD Drug ID
D09UZO
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
CNT2 Transporter Info Concentrative nucleoside transporter 2 Substrate [3]
CNT3 Transporter Info Concentrative Na(+)-nucleoside cotransporter 3 Substrate [4]
ENBT1 Transporter Info Equilibrative nucleobase transporter 1 Substrate [5]
ENT1 Transporter Info Equilibrative nucleoside transporter 1 Substrate [3]
ENT2 Transporter Info Equilibrative nucleoside transporter 2 Substrate [3]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [6]
MRP5 Transporter Info Multidrug resistance-associated protein 5 Substrate [7]
OAT3 Transporter Info Organic anion transporter 3 Substrate [8]
References
1 Mercaptopurine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 ABC transporters and their role in nucleoside and nucleotide drug resistance. Biochem Pharmacol. 2012 Apr 15;83(8):1073-83.
3 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA2040)
4 Involvement of the concentrative nucleoside transporter 3 and equilibrative nucleoside transporter 2 in the resistance of T-lymphoblastic cell lines to thiopurines. Biochem Biophys Res Commun. 2006 Apr 28;343(1):208-15.
5 Characterization of 6-Mercaptopurine Transport by the SLC43A3-Encoded Nucleobase Transporter. Mol Pharmacol. 2019 Jun;95(6):584-596.
6 Polymorphisms in multidrug resistance-associated protein gene 4 is associated with outcome in childhood acute lymphoblastic leukemia. Blood. 2009 Aug 13;114(7):1383-6.
7 Overexpression of MRP4 (ABCC4) and MRP5 (ABCC5) confer resistance to the nucleoside analogs cytarabine and troxacitabine, but not gemcitabine. Springerplus. 2014 Dec 13;3:732.
8 Organic anion transporter 3 is involved in the brain-to-blood efflux transport of thiopurine nucleobase analogs. J Neurochem. 2004 Aug;90(4):931-41.

If you find any error in data or bug in web service, please kindly report it to Dr. Li and Dr. Fu.