Thioguanine

Base Information

• Chemical Name: Thioguanine
• CAS No.: 154-42-7
• Molecular Formula: C5H5N5S
• Molecular Weight: 167.194
• Hs Code.: 29335990
• European Community (EC) Number: 205-827-2
• NSC Number: 757348,752
• UN Number: 2811
• UNII: WIX31ZPX66
• DSSTox Substance ID: DTXSID6023652
• Nikkaji Number: J21.274A
• Wikipedia: Tioguanine
• Wikidata: Q385347
• NCI Thesaurus Code: C61970
• RXCUI: 1546005
• Pharos Ligand ID: U8PQ7YG4YFSF
• Metabolomics Workbench ID: 42726
• ChEMBL ID: CHEMBL727
• Mol file: 154-42-7.mol

Synonyms:2 Amino 6 Purinethiol;2-amino-6-purinethiol;6 Thioguanine;6-Thioguanine;Anhydrous, Thioguanine;Lanvis;Tabloid;Thioguanin GSK;Thioguanin-GSK;Thioguanine;Thioguanine Anhydrous;Thioguanine Hemihydrate;Thioguanine Monosodium Salt;Thioguanine Tabloid;ThioguaninGSK;Tioguanina Wellcome;Tioguanine

Chemical Property of Thioguanine

Chemical Property:

• Appearance/Colour: Odorless or almost odorless pale yellow crystalline powder
• Vapor Pressure: 1.5E-17mmHg at 25°C
• Melting Point: ≥300 °C(lit.)
• Refractive Index: 1.5605 (estimate)
• Boiling Point: 555.4 °C at 760 mmHg
• PKA: pKa 8.22 (Uncertain)
• Flash Point: 289.7 °C
• PSA: 119.28000
• Density: 2.08 g/cm³
• LogP: 0.80500
• Storage Temp.: Store at RT.
• Solubility.: Practically insoluble in water and in ethanol (96%). It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: soluble
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 167.02656635
• Heavy Atom Count: 11
• Complexity: 225
• Transport DOT Label: Poison

Purity/Quality:

99%MIN ^*data from raw suppliers

6-Thioguanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-23/24/25
• Safety Statements: 28-36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1=NC2=C(N1)C(=S)N=C(N2)N
• Recent ClinicalTrials: Combination Chemotherapy in Treating Young Patients With Newly Diagnosed T-Cell Acute Lymphoblastic Leukemia or T-cell Lymphoblastic Lymphoma
• Recent EU Clinical Trials: TEMPLE - Thiopurine Enhanced Mutations for PD-1/Ligand-1 Efficacy
• Description: 6-Thioguanine (NSC 752, Thioguanine, 2-Amino-6-purinethiol), is an antineoplastic metabolic antagonist that inhibits DNA synthesis by being metabolically converted to 6-thioGMP. This inhibits purine biosynthesis at multiple steps, and may be phosphorylated and incorporated into DNA. In humans, it causes bone marrow depression and gastrointestinal toxicity. Due to safety problems it is currently less used as an antineoplastic agent but has some use as therapy for ulcerative colitis.
• Uses: 6-Thioguanine acts as an antineoplastic and purine antimetabolite. It is also useful as an inhibition of stimulated expression of TNF-related apoptosis-inducing ligand (TRAIL) protein. It is involved in the treatment of acute leukemias and Psoriasis. Further, it is used for the treatment of ulcerative colitis and autoimmune diseases.
• Indications: 6-Thioguanine is a purine analogue structurally related to 6-mercaptopurine and azathioprine. Thioguanine interferes with several enzymes required for de novo purine synthesis, and its metabolites are incorporated into DNA and RNA, further impeding nucleic acid synthesis. The mechanism of action of thioguanine in psoriasis is not clearly understood; it has been hypothesized to affect the proliferation and trafficking of lymphocytes as well as the proliferation of keratinocytes.
• Therapeutic Function: Cancer chemotherapy
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis).

Technology Process of Thioguanine

There total 14 articles about Thioguanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) → thioguanine (154-42-7)

Guidance literature:

With tetraphosphorus decasulfide; In sulfolane; at 160 - 165 ℃; for 4h;

DOI:10.1007/BF00771781

Reference yield:

N-(2,4-diamino-6-thioxo-1,6-dihydro-pyrimidin-5-yl)-formamide → thioguanin (154-42-7)

Guidance literature:

With sodium hydroxide; at 240 ℃;

DOI:10.1021/ja01593a062

Reference yield:

guanine (73-40-5) → thioguanin (154-42-7)

Guidance literature:

With pyridine; tetraphosphorus decasulfide;

DOI:10.1021/ja01611a082

upstream raw materials:

2-amino-6-chloropurine

guanine

2-amino-1,9-dihydro-6H-purin-6-one

9-(2,3-dideoxy-3-hydroxymethyl-α-D-erythro-pentofuranosyl)-6-thioguanine

Downstream raw materials:

2-(2-Amino-9H-purin-6-ylsulfanyl)-1-(4-nitro-phenyl)-ethanone

2-amino-9-(5-deoxy-β-D-ribofuranosyl)-9H-6-thiopurine

2-amino-6<(1-methyl-4-nitroimidazol-5-yl)-thio>purine

2-amino-1,9-dihydro-6H-purin-6-one

Refernces

• 1、 Kochergin,Aleksandrova,Tolvinskaya,Zhukova,Pukhal'skaya,Telegin,Pevnitskii,Korsunskii. "The synthesis and immunotropic activity of a new azathioprine analog - 2-Amino-6-(1-ethyl-2-methyl-4-nitroimidazolyl-5-mercapto)purine". . p. 579 - 581. Retrieved 2000.
• 2、 Tomsons, U. A.,Avots, A. A.,Kolesnikova, I. A.. "OPTIMIZATION OF THE TECHNOLOGY OF 6-THIOGUANINE PRODUCTION". . p. 136 - 138. Retrieved 1985.
• 3、 -. "THERAPEUTIC FOR HEPATIC CANCER". . . Retrieved 2011/02/18.
• 4、 Ren, Xiaolin,Xu, Yao-Zhong,Karran, Peter. "Photo-oxidation of 6-thioguanine by UVA: The formation of addition products with low molecular weight thiol compounds". body text. p. 1038 - 1045. Retrieved 2011/06/20.