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6-Thioguanine

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Products Intro: Product Name:6-Thioguanine
CAS:154-42-7
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CAS:154-42-7
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CAS:154-42-7
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Products Intro: Product Name:6-Thioguanine
CAS:154-42-7

6-Thioguanine manufacturers

  • 6-Thioguanine
  • $10.70 / g/Bag
  • 2021-12-01
  • CAS:154-42-7
  • Min. Order: 10g
  • Purity: 99%
  • Supply Ability: 10000kg
  • 6-Thioguanine
  • $0.00-0.00 / Kg
  • 2020-04-30
  • CAS:154-42-7
  • Min. Order: 1KG
  • Purity: 99.0%+
  • Supply Ability: 800 tons
6-Thioguanine Basic information
Product Name:6-Thioguanine
Synonyms:2-AMINO-6-PURINETHIOL;2-AMINO-6-MERCAPTOPURINE;2-aminopurine-6(1h)-thione;2-amino-purine-6(1h)-thion;2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol;5'-ribonucleotide;dibutyryl cyclic AMP calcium salt;complex coenzyme
CAS:154-42-7
MF:C5H5N5S
MW:167.19
EINECS:205-827-2
Product Categories:TABLOID;Nucleosides, Nucleotides & Related Reagents;Inhibitor;Bases & Related Reagents;Nucleotides;Sulfur & Selenium Compounds;Pyridines, Pyrimidines, Purines and Pteredines;Purine;All Inhibitors;Purines;Antitumors for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleobases and their analogs
Mol File:154-42-7.mol
6-Thioguanine Structure
6-Thioguanine Chemical 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)
pkapKa 8.22 (Uncertain)
form lyophilized powder
color Yellow to green
Water Solubility soluble
Merck 14,9337
BRN 157765
CAS DataBase Reference154-42-7(CAS DataBase Reference)
EPA Substance Registry SystemThioguanine (154-42-7)
Safety Information
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
Hazardous Substances Data154-42-7(Hazardous Substances Data)
ToxicityLD50 oral in mouse: 160mg/kg
MSDS Information
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6-Thioguanine English
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6-Thioguanine Usage And Synthesis
Chemical PropertiesCrystalline, lyophilized, sterile, endot
OriginatorThioguanine,Burroughs-Wellcome,US,1966
Usesantineoplastic, purine antimetabolite
UsesThe compound produced dose-dependent inhibition of stimulated expression of TRAIL protein
UsesThioguanine USP (Tabloid)is used to treat acute leukemia; chronic granulocytic leukemia.
IndicationsThioguanine 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.
Indications6-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.
DefinitionChEBI: A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine.
Manufacturing ProcessA 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 nameTioguanine is INN and BAN.
Therapeutic FunctionCancer chemotherapy
General DescriptionThe 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 DescriptionOdorless or almost odorless pale yellow crystalline powder.
Air & Water Reactions6-Thioguanine may be sensitive to prolonged exposure to air. Insoluble in water.
Reactivity Profile6-Thioguanine is incompatible with strong oxidizing agents. .
Fire HazardFlash point data for 6-Thioguanine are not available; however, 6-Thioguanine is probably combustible.
Mechanism of actionAbsorption 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 UseAlthough 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 effectsDose-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 ProfilePoison 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 SynthesisThioguanine, 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 TreatmentsThioguanine may be useful as adjunctive therapy for acute lymphocytic or granulocytic leukemia in dogs or cats.
Purification MethodsIt 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.]
Tag:6-Thioguanine(154-42-7) Related Product Information
Ancitabine Thioguanine deoxyriboside,β-Thioguanine deoxyriboside 6-Methylthioguanine 2-AMINO-9-(2,3,5-TRI-O-ACETYL-BETA-D-RIBOFURANOSYL)-6-THIOPURINE 8-Mercaptoguanine,8-Thioguanine 6-Thioguanosine hydrate 6-N-HEPTYLMERCAPTOPURINE 6,8-DIHYDROXY-2-METHYLMERCAPTOPURINE 6-(Methylthio)purine 6-thioinosine-5'-triphosphate 8-AZA-6-HYDROXY-2-MERCAPTOPURINE 1,7,8,9-tetrahydro-8-thioxo-6H-purin-6-one 6-METHYLMERCAPTOPURINE RIBOSIDE 2-Amino-6-mercaptopurine-13C2,15N 6-MERCAPTOPURINE RIBOSIDE 6-thioinosine 2',3',5'-triacetate 6-THIOXANTHINE 6-thioinosine 5'-monophosphate