Home > Compound List > Product Information
Thioguanine_Molecular_structure_CAS_154-42-7)
Click picture or here to close

Thioguanine

Catalog No. DB00352 Name DrugBank
CAS Number 154-42-7 Website http://www.ualberta.ca/
M. F. C5H5N5S Telephone (780) 492-3111
M. W. 167.1917 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 236

SYNONYMS

IUPAC name
2-amino-6,7-dihydro-3H-purine-6-thione
IUPAC Traditional name
thioguanine
Brand Name
Wellcome U3B
Lanvis
Tabloid
Synonyms
2-Amino-6-merkaptopurin
2-Aminopurine-6-thiol
2-Amino-6-purinethiol
ThG
Tioguanine
Tioguanin
6-Thioguanine
6-Mercaptoguanine
6-Mercapto-2-aminopurine
2-Aminopurine-6(1H)-thione
2-Aminopurin-6-thiol
2-Amino-6-mercaptopurine
2-Amino 6MP
TG

DATABASE IDS

PubChem CID 2723601
CAS Number 154-42-7
PubChem SID 46508170

PROPERTIES

Hydrophobicity(logP) -0.7
Solubility 36.3 mg/mL

DETAILS

Description (English)
Item Information
Drug Groups approved
Description An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia. [PubChem]
Indication For remission induction and remission consolidation treatment of acute nonlymphocytic leukemias.
Pharmacology Thioguanine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute nonlymphocytic leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Thioguanine was first synthesized and entered into clinical trial more than 30 years ago. It is a 6-thiopurine analogue of the naturally occurring purine bases hypoxanthine and guanine. Intracellular activation results in incorporation into DNA as a false purine base. An additional cytotoxic effect is related to its incorporation into RNA. Thioguanine is cross-resistant with mercaptopurine. Cytotoxicity is cell cycle phase-specific (S-phase).
Toxicity Oral, mouse: LD50 = 160 mg/kg. Symptoms of overdose include nausea, vomiting, malaise, hypotension, and diaphoresis.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. First converted to 6-thioguanilyic acid (TGMP). TGMP is further converted to the di- and tri-phosphates, thioguanosine diphosphate (TGDP) and thioguanosine triphosphate (TGTP) by the same enzymes that metabolize guanine nucleotides.
Absorption Absorption of an oral dose is incomplete and variable, averaging approximately 30% of the administered dose (range: 14% to 46%)
Half Life 80 minutes (range 25-240 minutes)
External Links
Wikipedia
RxList
Drugs.com

REFERENCES