Tioguanine

Tioguanine
Skeletal formula of tioguanine
Space-filling model of the tioguanine molecule
Clinical data
Trade namesLanvis, Tabloid, others
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682099
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability30% (range 14% to 46%)
MetabolismIntracellular
Elimination half-life80 minutes (range 25–240 minutes)
Identifiers
  • 2-amino-1H-purine-6(7H)-thione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.299 Edit this at Wikidata
Chemical and physical data
FormulaC5H5N5S
Molar mass167.19 g·mol−1
3D model (JSmol)
  • Nc2nc(=S)c1[nH]cnc1[nH]2
  • InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) checkY
  • Key:WYWHKKSPHMUBEB-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tioguanine, also known as thioguanine or 6-thioguanine (6-TG) or tabloid is a medication used to treat acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), and chronic myeloid leukemia (CML).[2] Long-term use is not recommended.[2] It is given by mouth.[2]

Common side effects include bone marrow suppression, liver problems and inflammation of the mouth.[2][3] It is recommended that liver enzymes be checked weekly when on the medication.[2] People with a genetic deficiency in thiopurine S-methyltransferase are at higher risk of side effects.[3] Avoiding pregnancy when on the medication is recommended.[2] Tioguanine is in the antimetabolite family of medications.[3] It is a purine analogue of guanine and works by disrupting DNA and RNA.[4]

Tioguanine was developed between 1949 and 1951.[5][6] It is on the World Health Organization's List of Essential Medicines.[7]

  1. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  2. ^ a b c d e f British National Formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 588, 592. ISBN 978-0-85711-156-2.
  3. ^ a b c "Tioguanine 40 mg Tablets – Summary of Product Characteristics (SPC) – (eMC)". www.medicines.org.uk. Archived from the original on 21 December 2016. Retrieved 21 December 2016.
  4. ^ Baca QJ, Coen DM, Golan DE (2011). "Principles of antimicrobial and antineoplastic therapy". In Golan DE, Tashjian AH, Armstrong EJ (eds.). Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Lippincott Williams & Wilkins. p. 686. ISBN 978-1-60831-270-2. Archived from the original on 2016-12-21.
  5. ^ Dubler E (1996). "Metal Complexes of Sulfur-Containing Purine Derivatives". In Sigel A, Sigel H (eds.). Metal Ions in Biological Systems. Vol. 32: Interactions of Metal Ions with Nucleotides: Nucleic Acids, and Their Constituents. CRC Press. p. 302. ISBN 978-0-8247-9549-8. Archived from the original on 2016-12-21.
  6. ^ Landau R, Achilladelis B, Scriabine A (1999). "Ch. 6. Clinical champions as critical determinants of drug development.". Pharmaceutical Innovation: Revolutionizing Human Health. Chemical Heritage Foundation. p. 342. ISBN 978-0-941901-21-5. Archived from the original on 2016-12-21.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.