Structure via PubChem · Public domain (PubChem)
6-thioguanine
Sign in to saveAlso known as 6-mercaptoguanine, 6-TG, TG, ThG, 2-amino-1,9-dihydropurine-6-thione, thioguanine anhydrous, tioguanin, 2-amino 6MP
Tioguanine, also known as thioguanine or 6-thioguanine (6-TG) , sold under the brand name Tabloid among others, is a medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), and chronic myeloid leukemia (CML). Long-term use is not recommended. It is given by mouth.
In the Vinony graph
Within Vinony's link graph, 6-thioguanine is referenced by 300 other articles, and connects out to chronic myeloid leukemia, zygosity and bone marrow suppression.
It is catalogued under topics including Drugboxes which contain changes to verified fields, Drugboxes which contain changes to watched fields and Drugs with non-standard legal status.
Its subject is documented across 24 Wikipedia language editions.
Chemical data
- Formula
- C5H5N5S
- Molecular weight
- 167.19 g/mol
- IUPAC name
- 2-amino-3,7-dihydropurine-6-thione
- SMILES
- C1=NC2=C(N1)C(=S)N=C(N2)N
- InChIKey
- WYWHKKSPHMUBEB-UHFFFAOYSA-N
- XLogP
- -0.1
- Polar surface area
- 111 Ų
- H-bond donors
- 3
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1966
- Admin. routes
- oral
- Indications
- non-Hodgkins lymphoma, neoplasm, acute lymphoblastic leukemia, Hodgkins lymphoma
via ChEMBL · EBI
Research
4,599 papers- 6-thioguanine: a drug with unrealized potential for cancer therapy.The oncologist · 2014
- 6-Thioguanine Inhibits Herpes Simplex Virus 1 Infection of Eyes.Microbiology spectrum · 2021
- 6-Thioguanine inhibits severe fever with thrombocytopenia syndrome virus through suppression of EGR1.Antiviral research · 2024
- 6-thioguanine-buried alive?Gastroenterology · 2004
- 6-thioguanine inhibits EV71 replication by reducing BIRC3-mediated autophagy.BMC microbiology · 2025
via PubMed
Wikidata facts
- Subclass of
- thiopurine
- Mass
- 167.027
- Has use
- medication
Show 6 more facts
- Commons category
- 6-Thioguanine
- found in taxon
- Pseudomonas
- chemical formula
- C₅H₅N₅S
- canonical SMILES
- C1=NC2=C(N1)C(=S)N=C(N2)N
- World Health Organisation international non-proprietary name
- tioguanine
- medical condition treated
- acute myeloid leukemia
Sources (6)
via Wikidata · CC0
~8 min read
Encyclopedic overview
12 sectionsContents
- Medical uses
- Side effects
- Hepatic veno-occlusive disease
- Contraindications
- Interactions
- Pharmacogenetics
- Metabolism and pharmacokinetics
- Mechanism of action
- Chemistry
- Names
- References
- Further reading
Tioguanine, also known as thioguanine or 6-thioguanine (6-TG) , sold under the brand name Tabloid among others, is a medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), and chronic myeloid leukemia (CML). Long-term use is not recommended. It is given by mouth.
Common side effects include bone marrow suppression, liver problems and inflammation of the mouth. It is recommended that liver enzymes be checked weekly when on the medication. People with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of side effects. Avoiding pregnancy when on the medication is recommended. Tioguanine is in the antimetabolite family of medications. It is a purine analogue of guanine and works by disrupting DNA and RNA.
Excerpted from Wikipedia’s “6-thioguanine” article, available under the CC BY-SA 4.0 licence.