Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00510
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| Drug Name |
Thioguanine
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| Synonyms |
2 Amino 6 Purinethiol; 2-Amino 6MP; 2-Amino-1,7-dihydro-6H-purin-6-thion; 2-Amino-1,7-dihydro-6H-purin-6-thion [Czech]; 2-Amino-1,7-dihydro-6H-purine-6-thione; 2-Amino-6-MP; 2-Amino-6-mercaptopurine; 2-Amino-6-merkaptopurin; 2-Amino-6-merkaptopurin [Czech]; 2-Amino-6-purinethiol; 2-Amino-9H-purine-6-thiol; 2-Aminopurin-6-thiol; 2-Aminopurin-6-thiol [Czech]; 2-Aminopurine-6(1H)-thione; 2-Aminopurine-6-thiol; 2-Thioguanine; 2-amino-3,7-dihydropurine-6-thione; 6 Thioguanine; 6-Mercapto-2-aminopurine; 6-Mercaptoguanine; 6-TG; 6-Thioguanine; 6-Thioguanine (6-TG); 6-Thioguanine, Thioguanine; BW 5071; DX4; Glaxo Wellcome Brand of Thioguanine; Glaxo Wellcome Brand of Tioguanine; GlaxoSmithKline Brand of Thioguanine; GlaxoSmithKline Brand of Tioguanine; Guanine, thio-(VAN); LT00455187; Lanvis; Lanvis (TN); Purine antimetabolite: antimetabolite: inhibits nucleic acid replication; THG; Tabloid; Thioguanin GSK; Thioguanin-GSK; ThioguaninGSK; Thioguanine (Guanine analog); Thioguanine Hemihydrate; Thioguanine Monosodium Salt; Thioguanine Tabloid; Thioguanine [USAN:BAN]; Tioguanin; Tioguanina; Tioguanina Wellcome; Tioguanina[INN-Spanish]; Tioguanine; Tioguanine (INN); Tioguanine GlaxoSmithKline Brand; Tioguaninum; Tioguaninum [INN-Latin]; Wellcome Brand of Thioguanine; Wellcome U3B
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| Drug Type |
Small molecular drug
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| Indication | Acute myeloid leukemia [ICD11:2A60] | Approved | [1] | |||
| Therapeutic Class |
Anticancer Agents
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| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C5H5N5S
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| Canonical SMILES |
C1=NC2=C(N1)C(=S)N=C(N2)N
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| InChI |
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
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| InChIKey |
WYWHKKSPHMUBEB-UHFFFAOYSA-N
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| CAS Number |
CAS 154-42-7
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| Pharmaceutical Properties | Molecular Weight | 167.19 | Topological Polar Surface Area | 111 | ||
| Heavy Atom Count | 11 | Rotatable Bond Count | 0 | |||
| Hydrogen Bond Donor Count | 3 | Hydrogen Bond Acceptor Count | 2 | |||
| XLogP |
-0.1
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| PubChem CID | ||||||
| PubChem SID |
11335603
,11360842
,11363129
,11364886
,11365691
,11367448
,11368253
,11370010
,11371594
,11373049
,11374590
,11375610
,11376415
,11378179
,11445995
,11451636
,11461814
,11484585
,11488511
,11490393
,11492741
,11494049
,14772534
,15171129
,16902289
,23926847
,24890748
,24890892
,26611944
,26679349
,26748270
,26748271
,26748272
,30081936
,3131990
,37587702
,4361010
,4364659
,46508170
,47365125
,48094105
,48110398
,48110399
,538243
,5646737
,610358
,6425700
,7980774
,8149552
,9850
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| ChEBI ID |
CHEBI:9555
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | BCRP | Transporter Info | Breast cancer resistance protein | Substrate | [2] | |
| CNT3 | Transporter Info | Concentrative Na(+)-nucleoside cotransporter 3 | Substrate | [3] | ||
| MRP4 | Transporter Info | Multidrug resistance-associated protein 4 | Substrate | [4] | ||
| References | ||||||
| 1 | Thioguanine 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 | 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. | |||||
| 4 | Multidrug resistance protein 4 (MRP4/ABCC4) mediates efflux of bimane-glutathione. Int J Biochem Cell Biol. 2004 Feb;36(2):247-57. | |||||
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