88800

6-Thioguanine

purum, ≥96% (HPLC)

• Synonym(s): 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
• Empirical Formula (Hill Notation): C₅H₅N₅S
• CAS Number: 154-42-7
• Molecular Weight: 167.19
• EC Number: 205-827-2
• UNSPSC Code: 12352202
• MDL number: MFCD00233553
• Beilstein/REAXYS Number: 157765

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P310
• 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