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6-Thioguanine

6-Thioguanine
6-Thioguanine structure
CAS No.
154-42-7
Chemical Name:
6-Thioguanine
Synonyms
6-tg;bw5071;lanvis;nsc-752;tabloid;tioguanin;tioguanine;Guanine, t;thio-guanin;wellcomeu3b
CBNumber:
CB6361837
Molecular Formula:
C5H5N5S
Formula Weight:
167.19
MOL File:
154-42-7.mol

6-Thioguanine Properties

Melting point:
≥300 °C(lit.)
Density 
1.483 (estimate)
refractive index 
1.5605 (estimate)
storage temp. 
2-8°C
solubility 
Practically insoluble in water and in ethanol (96%). It dissolves in dilute solutions of alkali hydroxides.
Boiling point:
555.4±42.0 °C(Predicted)
pka
pKa 8.22 (Uncertain)
form 
lyophilized powder
color 
Yellow to green
Water Solubility 
soluble
Merck 
14,9337
BRN 
157765
CAS DataBase Reference
154-42-7(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
Tabloid; thioguanine
FDA UNII
FTK8U1GZNX
Proposition 65 List
Thioguanine
NCI Drug Dictionary
Tabloid
ATC code
L01BB03
EPA Substance Registry System
Thioguanine (154-42-7)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06,GHS07
Signal word  Danger
Hazard statements  H315-H319-H301
Precautionary statements  P301+P310-P301+P310a-P321-P501a-P264-P270-P280-P301+P310+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P405-P501
Hazard Codes  T,Xi
Risk Statements  25-23/24/25
Safety Statements  28-36/37/39-45-28A
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  UP0740000
13
Hazard Note  Irritant
HazardClass  6.1
PackingGroup  III
HS Code  29335990
Toxicity LD50 oral in mouse: 160mg/kg

6-Thioguanine price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A4660 6-Thioguanine Hybri-Max , 50 ×, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma 154-42-7 2.5mg $22.1 2021-03-22 Buy
Sigma-Aldrich 1660000 Thioguanine United States Pharmacopeia (USP) Reference Standard 154-42-7 200mg $350 2021-03-22 Buy
TCI Chemical T0212 6-Thioguanine >95.0%(HPLC) 154-42-7 1g $86 2021-03-22 Buy
TCI Chemical T0212 6-Thioguanine >95.0%(HPLC) 154-42-7 5g $256 2021-03-22 Buy
Alfa Aesar B21280 6-Thioguanine, 98% 154-42-7 5g $292 2021-03-22 Buy

6-Thioguanine Chemical Properties,Uses,Production

Chemical Properties

Crystalline, lyophilized, sterile, endot

Originator

Thioguanine,Burroughs-Wellcome,US,1966

Uses

antineoplastic, purine antimetabolite

Uses

The compound produced dose-dependent inhibition of stimulated expression of TRAIL protein

Uses

Thioguanine USP (Tabloid)is used to treat acute leukemia; chronic granulocytic leukemia.

Indications

Thioguanine is an analogue of the natural purine guanine in which a hydroxyl group has been replaced by a sulfhydryl group in the 6-position. Two major mechanisms of cytotoxicity have been proposed for 6-thioguanine: (1) incorporation of the thio nucleotide analogue into DNA or RNA and (2) feedback inhibition of purine nucleotide synthesis.
The product of this reaction, 6-TGMP, can eventually be converted to deoxy-6-thioguanosine-triphosphate (dTGTP), which has been shown to be incorporated into DNA. Resistance of human leukemia cells to thioguanine has been correlated with decreased activity of HGPRTase and to increased inactivation of the thio nucleotides by alkaline phosphatase.
Thioguanine is slowly absorbed after oral administration; parent drug levels are barely detectable, and peak levels of metabolites occur only after 6 to 8 hours. Total urinary excretion of metabolites in the first 24 hours is 24 to 46% of the administered dose.
Thioguanine is used primarily as part of a combined induction of chemotherapy in acute myelogenous leukemia.
Myelosuppression, with leukopenia and thrombocytopenia appearing 7 to 10 days after treatment, and mild nausea are the most common adverse effects. Liver toxicity with jaundice has been reported in some patients but appears to be less common than with mercaptopurine.

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.

Definition

ChEBI: A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine.

Manufacturing Process

A mixture of 2.7 grams of finely divided guanine, 10 grams of pulverized phosphorus pentasulfide, 10 ml of pyridine and 100 ml of tetralin was heated at 200°C with mechanical stirring for 5 hours. After cooling, the mixture was filtered and the insoluble residue treated with 150 ml of water and 50 ml of concentrated ammonium hydroxide. The ammoniacal solution was filtered, heated to boiling and acidified with acetic acid. Upon cooling, 2-amino-6- mercaptopurine precipitated as a dark yellow powder, according to US Patent 2,697,709.

brand name

Tioguanine is INN and BAN.

Therapeutic Function

Cancer chemotherapy

General Description

The drug is available in 40-mg tablets for oral use.Thioguanine is used to treat acute nonlymphocytic leukemia.The mechanism of action involves incorporation of thetriphosphate into DNA and RNA, resulting in inhibition ofprocessing and function. Intracellular phosphorylation is requiredfor activity and inhibition of purine biosynthesis.Resistance can include decreased expression of the activatingenzyme, decreased drug transport, and/or increased expressionof catabolic enzymes. The oral absorption ofthioguanine is poor, and the drug does not appear to cross theblood-brain barrier. Major metabolic pathways involvedeamination or methylation. Thioguanine is not a substratefor the enzyme xanthine oxidase in contrast to mercaptopurine.Toxicities include myelosuppression, immunosuppression,nausea, vomiting, mucositis, and diarrhea.

General Description

Odorless or almost odorless pale yellow crystalline powder.

Air & Water Reactions

6-Thioguanine may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

6-Thioguanine is incompatible with strong oxidizing agents. .

Fire Hazard

Flash point data for 6-Thioguanine are not available; however, 6-Thioguanine is probably combustible.

Mechanism of action

Absorption of orally administered 6-thioguanine is slow and incomplete; only approximately 30% of the oral dose is achieved in the plasma, peak levels being reached after 8 hours. Thioguanine is extensively metabolized prior to excretion. The elimination half-life is on the order of 80 minutes.

Clinical Use

Although 6-thioguanine is chiefly used in chemotherapy for acute myelocytic leukemia and other marrow-based malignancies, lower doses are very effective for moderate to severe psoriasis, particularly in patients who cannot tolerate alternative systemic agents such as methotrexate and cyclosporine.

Side effects

Dose-related myelosuppression is the major adverse effect produced by 6-thioguanine. Patients deficient in thiopurine methyltransferase (TPMT), a cytosolic enzyme required for metabolism of 6-thioguanine, are at heightened risk. Other adverse effects include gastrointestinal complaints and elevations of liver transaminases. There have been rare reports of more serious hepatotoxicity, including acute hepatitis, acute cholestasis, and hepatic venoocclusive disease.

Safety Profile

Poison by ingestion andintraperitoneal routes. Human mutation data reported. Anexperimental teratogen. Other reproductive effects. Ahuman skin irritant. When heated to decomposition itemits very toxic fumes of SOx and NOx.

Chemical Synthesis

Thioguanine, 2-aminopurin-6-thiol (30.1.2.12), is made from 2,8-dichloro- 6-hydroxypurine (30.1.2.7), in which the second chlorine atom at C2 is replaced with an amino group when reacted with ammonia, forming 2-amino-8-chloro-6-hydroxy-purine (30.1.2.7), which is then reduced by hydrogen iodide to 2-aminopurin-6-ol (30.1.2.11). Replacement of the hydroxyl group with a mercapto group at C6 is carried out by reacting it with phosphorous pentasulfide, which forms thioguanine (30.1.2.12).

Veterinary Drugs and Treatments

Thioguanine may be useful as adjunctive therapy for acute lymphocytic or granulocytic leukemia in dogs or cats.

Purification Methods

It crystallises from H2O as needles. It has UV at 258 and 347nm (H2O, pH 1) and 242, 270 and 322nm max (H2O, pH 11). [Elion & Hitchings J Am Chem Soc 77 1676 1955, Fox et al. J Am Chem Soc 80 1669 1958.] It is an antineoplastic agent [Kataoka et al. Cancer Res 44 519 1984]. [Beilstein 26 III/IV 3926.]

6-Thioguanine Preparation Products And Raw materials

Raw materials

Preparation Products


6-Thioguanine Suppliers

Global( 262)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2941 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
Hubei xin bonus chemical co. LTD
86-13657291602
027-59338440 linda@hubeijusheng.com CHINA 23035 58
Shandong chuangyingchemical Co., Ltd.
18853181302
sale@chuangyingchem.com CHINA 5917 58
Chongqing Chemdad Co., Ltd
+86-13650506873
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CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47498 58
career henan chemical co
13203830695 0086-371-86658258
0086-371-86658258 factory@coreychem.com CHINA 29864 58
Shaanxi Dideu Medichem Co. Ltd
15319487004
029-88380327 1015@dideu.com CHINA 4105 58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd
13580539051
joe@yuhengpharm.com CHINA 21151 58

View Lastest Price from 6-Thioguanine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-08-26 6-Thioguanine
154-42-7
US $10.70 / g/Bag 10g 99% 10000kg Hebei Crovell Biotech Co Ltd
2021-07-02 6-Thioguanine USP/EP/BP
154-42-7
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
2020-04-30 6-Thioguanine
154-42-7
US $0.00-0.00 / Kg 1KG 99.0%+ 800 tons Shaanxi Dideu Medichem Co. Ltd

6-Thioguanine Spectrum


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