Basic information
- Standard SMILES
OC[C@H]1O[C@@H](n2cnc3c(=S)nc[nH]c32)[C@H](O)[C@@H]1O- InChIKey
NKGPJODWTZCHGF-KQYNXXCUSA-N- Molecular formula
- C10H12N4O4S
- Average molar mass
- 284.29 g/mol
Overview
Thioinosine is a sulfhydryl analog of inosine and an antimetabolite with potential antineoplastic and immunosuppressive properties. Thioinosine interferes with de novo purine synthesis and perturbs the pool of nucleotides necessary for DNA replication. As a result, this agent inhibits DNA synthesis, blocks cellular proliferation and induces apoptosis.
Names & identifiers
- Preferred name
- 6-Thioinosine
- IUPAC
- 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
Names & synonyms
574-25-46-ThioinosineTHIOINOSINERibosyl-6-thiopurineMercaptopurine ribonucleosideMercaptopurine riboside6-Mercaptopurine ribonucleoside6H-Purine-6-thione, 1,9-dihydro-9-ribofuranosyl-9H-Purine-6(1H)-thione, 9-beta-D-ribofuranosyl-46S541971TRibosyl-6-mercaptopurineRibosyl 6 mercaptopurine
Show more names
6 Mercaptopurine RibosideRiboside, 6-MercaptopurineNSC4911inosine, 6-thioRefChem:189543DTXCID301478415209-371-5DTXSID5046019
Database identifiers
- CAS
4988-64-1、574-25-4- PubChem CID
- 676166
- ChEMBL
CHEMBL448290- UNII
- 46S541971T
- EC Number
- 209-371-5
- Nikkaji
- J33.135J
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 144 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 409
Experimental & physicochemical properties
LogP-0.6
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Antimetabolites that are useful in cancer chemotherapy.
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysAzathioprine Action Pathway
Related reactions
4 records
Linked notes
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