Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H13N5O4S |
Molecular Weight | 299.306 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=S)N1
InChI
InChIKey=OTDJAMXESTUWLO-UUOKFMHZSA-N
InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1
6-Thioguanosine (or thioguanosine) is a metabolite of 6-thioguanine, an immunosuppressant and anticancer prodrug, and plays a major role in the prodrug's overall photoreactivity. 6-Thioguanosine has been shown to induce DNA damage and cell death upon exposure to UVA radiation, which is correlated to the significant increase in skin cancers following prolonged treatment with thiopurine prodrug. Also existed experiments where 6-thioguanosine was used to treat idiopathic myocardial hypertrophy and where it showed clinical value in cancer chemotherapy.
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/4359880 |
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Clinical evaluation of thioguanosine. | 1961 Sep |
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Purine analogs as potential anticytomegalovirus agents. | 1969 Sep |
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Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds. | 1997 Sep-Oct |
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IMP dehydrogenase basal activity in MOLT-4 human leukaemia cells is altered by mycophenolic acid and 6-thioguanosine. | 2008 |
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Excited-State Dynamics of the Thiopurine Prodrug 6-Thioguanine: Can N9-Glycosylation Affect Its Phototoxic Activity? | 2017 Feb 28 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18609073
Curator's Comment: inosine 5'-monophosphate dehydrogenase basal activity in MOLT-4 human leukaemia cells is reduced by 6-thioguanosine
Unknown
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C558LI0K8P
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201-597-2
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m10761
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SUB195657
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100000181870
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85-31-4
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DTXSID201018977
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C005783
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29422
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2724387
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SUBSTANCE RECORD