Tioguanine

Tioguanine
Clinical data
Trade names	Lanvis, Tabloid, others
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682099
License data	US DailyMed: thioguanine;
Routes of; administration	By mouth
ATC code	L01BB03 (WHO) ;
Legal status
Legal status	CA: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	30% (range 14% to 46%)
Metabolism	Intracellular
Elimination half-life	80 minutes (range 25–240 minutes)
Identifiers
	IUPAC name 2-amino-1H-purine-6(7H)-thione;
CAS Number	154-42-7 ;
PubChem CID	2723601;
IUPHAR/BPS	6845;
DrugBank	DB00352 ;
ChemSpider	2005804 ;
UNII	WIX31ZPX66;
KEGG	D08603 ;
ChEBI	CHEBI:9555 ;
ChEMBL	ChEMBL727 ;
CompTox Dashboard (EPA)	DTXSID6023652 ;
ECHA InfoCard	100.005.299
Chemical and physical data
Formula	C5H5N5S
Molar mass	167.19 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Nc2nc(=S)c1[nH]cnc1[nH]2;
	InChI InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) ; Key:WYWHKKSPHMUBEB-UHFFFAOYSA-N ;
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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]

^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ ^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.
^ ^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.
^ 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.
^ 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.
^ 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.
^ 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.

[1] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[BNF69-2] ^ ^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.

[UK2016-3] "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.

[WHO21st-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.

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