88800
6-Thioguanine
purum, ≥96% (HPLC)
Synonym(s):
2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
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About This Item
Empirical Formula (Hill Notation):
C5H5N5S
CAS Number:
Molecular Weight:
167.19
EC Number:
205-827-2
UNSPSC Code:
12352202
MDL number:
Beilstein/REAXYS Number:
157765
grade
purum
assay
≥96% (HPLC)
impurities
≤3% guanine
mp
≥300 °C (lit.)
SMILES string
NC1=Nc2nc[nH]c2C(=S)N1
InChI
1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.
Other Notes
Antineoplastic agent; substrate for HGPRTase, converted to 6-thio-GMP, which then inhibits vital metabolic sequences in myelocytic and acute lymphocytic leukemia.
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signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Regulatory Information
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Galal H Elgemeie
Current pharmaceutical design, 9(31), 2627-2642 (2003-10-08)
6-Mercaptopurine (6MP) and 6-thioguanine (6TG) are analogs of the natural purines: hypoxanthine and guanine. Both mercaptopurine and thioguanine are substrates for hypoxanthine-guanine phosphoribosyltransferase and are converted into the ribonucleotides 6-thioguanosine monophosphate (6-thioGMP) and 6-thioinosine monophosphate (T-IMP) respectively. The accumulation of
T Kataoka et al.
Cancer research, 44(2), 519-524 (1984-02-01)
While the combination of L1210 murine leukemia cell vaccine (L1210 vaccine) with 6-mercaptopurine (6-MP) or 6-thioguanine produces a therapeutic response greater than that induced by either of these agents alone, its combination with cyclophosphamide, N4-behenoyl-1-beta-D-arabinofuranosylcytosine, or 5-fluorouracil does not produce
Mark Drost et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(23), 9403-9408 (2013-05-22)
In many individuals suspected of the common cancer predisposition Lynch syndrome, variants of unclear significance (VUS), rather than an obviously pathogenic mutations, are identified in one of the DNA mismatch repair (MMR) genes. The uncertainty of whether such VUS inactivate