Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1597)
Drug Name
BW-5071
Synonyms
Tioguanine; Guanine, thio-; Lanvis; Purine-6(1H)-thione, 2-amino-; Purine-6-thiol, 2-amino-; Tabloid; Tioguanin; Tioguanina; Tioguaninum; Wellcome U3B; thioguanine; 154-42-7; 2-Amino 6MP; 2-Amino-6-MP; 2-Amino-6-mercaptopurine; 2-Amino-6-merkaptopurin; 2-Amino-6-purinethiol; 2-Amino-9H-purine-6-thiol; 2-Aminopurin-6-thiol; 2-Aminopurine-6(1H)-thione; 2-Aminopurine-6-thiol; 2-Thioguanine; 6-Mercapto-2-aminopurine; 6-Mercaptoguanine; 6-TG; 6-Thioguanine; 6H-Purine-6-thione, 2-amino-1,7-dihydro-; BW 5071
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Phase 1/2 [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
PubChem CID
2723601
PubChem SID
9850 ; 538243 ; 610358 ; 3131990 ; 4361010 ; 4364659 ; 5646737 ; 6425700 ; 7980774 ; 8149552 ; 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 ; 37587702 ; 46508170 ; 47365125 ; 48094105 ; 48110398 ; 48110399
ChEBI ID
CHEBI:9555
CAS Number
154-42-7
TTD Drug ID
D02ZXM
Formula
C5H5N5S
Canonical SMILES
C1=NC2=C(N1)C(=S)N=C(N2)N
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Methyl-thioguanosine monophosphate DM005704
129661584
Unclear 1 [3]
Thioguanosine monophosphate DM005699
137219742
Unclear 1 [2]
Thioguanosine diphosphate DM005700
137250051
Unclear 2 [2]
Thiodeoxyguanosine diphosphate DM005701
129858633
Unclear 3 [2]
Thioguanosine triphosphate DM005702
136408906
Unclear 3 [2]
Thiodeoxyguanosine triphosphate DM005703
164888485
Unclear 4 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006082 BW-5071 Thioguanosine monophosphate Unclear HPRT1 [2]
MR006087 BW-5071 Methyl-thioguanosine monophosphate Unclear TPMT [3]
MR006083 Thioguanosine monophosphate Thioguanosine diphosphate Unclear HPRT1 [2]
MR006084 Thioguanosine diphosphate Thiodeoxyguanosine diphosphate Unclear HPRT1 [2]
MR006085 Thioguanosine diphosphate Thioguanosine triphosphate Unclear HPRT1 [2]
MR006086 Thiodeoxyguanosine diphosphate Thiodeoxyguanosine triphosphate Unclear HPRT1 [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Hypoxanthine phosphoribosyltransferase (HPRT1) DME0223 Homo sapiens
HPRT_HUMAN
2.4.2.8
[2]
Thiopurine methyltransferase (TPMT) DME0014 Homo sapiens
TPMT_HUMAN
2.1.1.67
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Thiopurine methyltransferase (TPMT) DME0014 Km = 0.0152 microM
TPMT_HUMAN
[4]
References
1 ClinicalTrials.gov (NCT02912676) Thiopurine EnhAnced Maintenance Therapy.
2 Qualitative and quantitative difference in mutation induction between carbon- and neon-ion beams in normal human cells. Biol Sci Space. 2003 Dec;17(4):302-6.
3 Usefulness of thiopurine methyltransferase and thiopurine metabolite analysis in clinical practice in patients with inflammatory bowel diseases. Acta Gastroenterol Belg. 2010 Jul-Sep;73(3):331-5.
4 Identification and functional analysis of two rare allelic variants of the thiopurine S-methyltransferase gene, TPMT*16 and TPMT*19. Biochem Pharmacol. 2005 Feb 1;69(3):525-9.

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