2-amino-6,7-dihydro-3H-purine-6-thione

• ChemBase ID: 236
• Molecular Formular: C5H5N5S
• Molecular Mass: 167.1917
• Monoisotopic Mass: 167.02656619
• SMILES: S=c1nc([nH]c2nc[nH]c12)N
• Canonical SMILES: Nc1nc(=S)c2c([nH]1)nc[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)
• InChIKey: WYWHKKSPHMUBEB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 154-42-7
• PubChem SID: 160963699; 46508170
• PubChem CID: 2723601

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.526401
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.35059884
• LogD (pH = 7.4): -0.34978372
• Log P: -0.34946936
• Molar Refractivity: 46.892 cm^3
• Polarizability: 16.556705 Å^3
• Polar Surface Area: 79.09 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.36
• LOG S: -2.3
• Solubility (Water): 8.34e-01 g/l

PROPERTIES

Physical Property

• Solubility: 36.3 mg/mL
• Hydrophobicity(logP): -0.7

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00352

• 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

Selleck Chemicals - S1774

Research Area: Cancer
Biological Activity:
The thiopurine drugs are purine antimetabolites widely used in the treatment of acute lymphoblastic leukemia, autoimmune disorders (e.g., Crohn’s disease, rheumatoid arthritis) and organ transplant recipients. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Thiopurine