Details of the Drug

General Information of Drug (ID: DM7RMG9)

Drug Name
Thioguanine
Synonyms
6-thioguanine; Lanvis; THG; Tabloid; ThioguaninGSK; Tioguanin; Tioguanina; Tioguanine; Tioguaninum; Glaxo Wellcome Brand of Thioguanine; Glaxo Wellcome Brand of Tioguanine; GlaxoSmithKline Brand of Thioguanine; GlaxoSmithKline Brand of Tioguanine; Thioguanin GSK; Thioguanine Hemihydrate; Thioguanine Monosodium Salt; Thioguanine Tabloid; Tioguanina Wellcome; Tioguanine GlaxoSmithKline Brand; Wellcome Brand of Thioguanine; BW 5071; DX4; LT00455187; Wellcome U3B; Lanvis (TN); Thioguanin-GSK; Thioguanine [USAN:BAN]; Tioguanina[INN-Spanish]; Tioguanine (INN); Tioguaninum [INN-Latin]; Purine antimetabolite: antimetabolite: inhibits nucleic acid replication; Guanine, thio-(VAN); 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; Thioguanine (Guanine analog)
Indication
Disease Entry ICD 11 Status REF
Acute lymphocytic leukaemia 2B33.3 Approved [1]
Middle East Respiratory Syndrome (MERS) 1D64 Preclinical [2]
Severe acute respiratory syndrome (SARS) 1D65 Preclinical [2]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 167.19
Topological Polar Surface Area (xlogp) -0.1
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 80 minutes [3]
Metabolism
The drug is metabolized via the hepatic [4]
Chemical Identifiers
Formula
C5H5N5S
IUPAC Name
2-amino-3,7-dihydropurine-6-thione
Canonical SMILES
C1=NC2=C(N1)C(=S)N=C(N2)N
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)
InChIKey
WYWHKKSPHMUBEB-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2723601
ChEBI ID
CHEBI:9555
CAS Number
154-42-7
DrugBank ID
DB00352
TTD ID
D0BK1N
ACDINA ID
D00671

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
MERS-CoV papain-like proteinase (PL-PRO) TTYJOLE R1AB_CVEMC (854-2740) Inhibitor [2]
SARS-CoV papain-like proteinase (PL-PRO) TTRGHB2 R1AB_CVHSA (819-2740) Inhibitor [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Thiopurine analogs and mycophenolic acid synergistically inhibit the papain-like protease of Middle East respiratory syndrome coronavirus. Antiviral Res. 2015 Mar;115:9-16.
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5 Therapeutic options for the 2019 novel coronavirus (2019-nCoV). Nat Rev Drug Discov. 2020 Mar;19(3):149-150.
6 Identification and Design of Novel Small Molecule Inhibitors Against MERS-CoV Papain-Like Protease via High-Throughput Screening and Molecular Modeling Bioorg Med Chem. 2019 May 15;27(10):1981-1989.
7 SARS and MERS: recent insights into emerging coronaviruses. Nat Rev Microbiol. 2016 Aug;14(8):523-34.
8 Severe acute respiratory syndrome coronavirus papain-like novel protease inhibitors: design, synthesis, protein-ligand X-ray structure and biologic... J Med Chem. 2010 Jul 8;53(13):4968-79.