6-Thioguanine
- Product Name
- 6-Thioguanine
- CAS No.
- 154-42-7
- Chemical Name
- 6-Thioguanine
- Synonyms
- THIOGUANINE;tioguanine;6-tg;2-AMINO-6-PURINETHIOL;lanvis;6-MERCAPTOGUANINE;2-AMINO-6-MERCAPTOPURINE;2-Amino-3,7-dihydropurine-6-thione;2-Amino-3,7-dihydro-6H-purine-6-thione;6H-Purine-6-thione, 2-amino-1,9-dihydro-
- CBNumber
- CB6361837
- Molecular Formula
- C5H5N5S
- Formula Weight
- 167.19
- MOL File
- 154-42-7.mol
6-Thioguanine Property
- 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)
- form
- lyophilized powder
- pka
- pKa 8.22 (Uncertain)
- color
- Yellow to green
- Water Solubility
- soluble
- Merck
- 14,9337
- BRN
- 157765
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMF may be stored at -20°C for up to 1 month.
- CAS DataBase Reference
- 154-42-7(CAS DataBase Reference)
- EPA Substance Registry System
- Thioguanine (154-42-7)
Safety
- 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
- F
- 13
- Hazard Note
- Irritant
- HazardClass
- 6.1
- PackingGroup
- III
- HS Code
- 29335990
- Hazardous Substances Data
- 154-42-7(Hazardous Substances Data)
- Toxicity
- LD50 oral in mouse: 160mg/kg
N-Bromosuccinimide Price
- Product number
- PHR3250
- Product name
- Thioguanine
- Purity
- pharmaceutical secondary standard, certified reference material
- Packaging
- 500MG
- Price
- $201
- Updated
- 2024/03/01
- Product number
- BP878
- Product name
- Tioguanine
- Purity
- British Pharmacopoeia (BP) Reference Standard
- Packaging
- 100MG
- Price
- $257
- Updated
- 2024/03/01
- Product number
- A4660
- Product name
- 6-Thioguanine
- Purity
- Hybri-Max , 50 ×, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma
- Packaging
- 2.5mg
- Price
- $26.7
- Updated
- 2024/03/01
- Product number
- 1660000
- Product name
- Thioguanine
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 200mg
- Price
- $164.8
- Updated
- 2024/03/01
- Product number
- T0212
- Product name
- 6-Thioguanine
- Purity
- >95.0%(HPLC)
- Packaging
- 1g
- Price
- $94
- Updated
- 2024/03/01
6-Thioguanine Chemical Properties,Usage,Production
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.
Chemical Properties
Crystalline, lyophilized, sterile, endot. It is white or slightly yellow powder with umami taste, easily soluble in water, but insoluble in organic solvents such as ethanol and acetone.
Originator
Thioguanine,Burroughs-Wellcome,US,1966
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.
Definition
ChEBI: 6-Thioguanine is a 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine.
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.
Application
6-Thioguanine is a variant of guanine with hydrogen bonding at the N-7 of the purine ring. Its association with cytosine alters the dimension of the base stacking. 6-Thioguanine usage in treating inflammatory bowel disease (IBD) contributes to nodular regenerative hyperplasia (NRH) in the liver.
6-Thioguanine has been used:
to induce autophagy and apoptosis in colorectal cancer cell lines HCT116
as a selection marker in the mutation and survival assay in chinese hamster lung fibroblasts culture V79
as a selection marker in clonogenic Lung metastasis assay of 4T1-luc cells
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
6-thioguanine appears as odorless or almost odorless pale yellow crystalline powder. The drug is available in 40-mg tablets for oral use. It is used to treat acute nonlymphocytic leukemia.
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.
Biochem/physiol Actions
Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia.
Mechanism of action
The mechanism of action involves incorporation of thetriphosphate into DNA and RNA, resulting in inhibition ofprocessing and function. Thioguanine is a purine antagonist. It is a pro-drug that is converted intracellullarly directly to thioguanine monophosphate (also called 6-thioguanylic acid) (TGMP) by the enzyme hypoxanthine-guanine phosphoribosyl transferase (HGPRT). TGMP is further converted to the di- and triphosphates, thioguanosine diphosphate (TGDP) and thioguanosine triphosphate (TGTP). The cytotoxic effect of thioguanine is a result of the incorporation of these nucleotides into DNA. Thioguanine has some immunosuppressive activity.1 Thioguanine is specific for the S phase of the cell cycle.
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.
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.
Drug interactions
Potentially hazardous interactions with other drugs
Antipsychotics: avoid concomitant use with
clozapine (increased risk of agranulocytosis).
Metabolism
Tioguanine undergoes extensive metabolism in the liver and other tissues to several active and inactive metabolites. Tioguanine is inactivated mainly by methylation to aminomethylthiopurine; small amounts are deaminated to thioxanthine, and may go on to be oxidised by xanthine oxidase to thiouric acid, but inactivation is essentially independent of xanthine oxidase and is not affected by inhibition of the enzyme. 24-46
% of the dose is excreted in the urine within 24 hours. It is excreted in the urine almost entirely as metabolites
storage
Room temperature
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.]
References
1) Wang and Wang (2009), 6-thioguanine perturbs cytosine methylation at the CpG dinucleotide site by DNA methyltransferases in vitro and acts as a DNA demethylating agent in vivo; Biochemistry, 48 2290
2) Yuan et al. (2011), 6-thioguanine reactivates epigenetically silenced genes in acute lymphoblastic leukemia cells by facilitating proteasome-mediated degradation of DNMT1; Cancer Res., 71 1904
3) Bohon and de los Santos (2005), Effect of 6-thioguanine on the stability of duplex DNA; Nucleic Acid Res., 33 2880
4) Issaeva et al. (2010), 6-thioguanine selectively kills BRCA2-defective tumors and overcomes PARP inhibitor resistance; Cancer Res., 70 6268
6-Thioguanine Preparation Products And Raw materials
Raw materials
Preparation Products
6-Thioguanine Suppliers
- Tel
- 027-59225746 18062681621
- Fax
- 027-59225746
- 730880265@qq.com
- Country
- China
- ProdList
- 4793
- Advantage
- 58
- Tel
- 010-82848833 400-666-7788
- Fax
- 86-10-82849933
- jkinfo@jkchemical.com
- Country
- China
- ProdList
- 94838
- Advantage
- 76
- Tel
- 4006608290; 18621169109
- Fax
- 86-21-61259102
- market03@meryer.com
- Country
- China
- ProdList
- 40241
- Advantage
- 62
- Tel
- 821-50328103-801 18930552037
- Fax
- 86-21-50328109
- 3bsc@sina.com
- Country
- China
- ProdList
- 15848
- Advantage
- 69
- Tel
- 400-6106006
- Fax
- 021-67582001/03/05
- saleschina@alfa-asia.com
- Country
- China
- ProdList
- 30132
- Advantage
- 84
- Tel
- 021-67121386
- Fax
- 021-67121385
- Sales-CN@TCIchemicals.com
- Country
- China
- ProdList
- 24539
- Advantage
- 81
- Tel
- 021-021-58432009 400-005-6266
- Fax
- 021-58436166
- sales8178@energy-chemical.com
- Country
- China
- ProdList
- 44751
- Advantage
- 61
- Tel
- +86 (0) 571 85 58 67 18
- Fax
- 0086-571-85864795
- sales@capotchem.com
- Country
- China
- ProdList
- 18217
- Advantage
- 66
- Tel
- 400-6009262 16621234537
- Fax
- 021-64823266
- zhangsn@titansci.com
- Country
- China
- ProdList
- 14113
- Advantage
- 59
- Tel
- 021-54306202 13764082696;
- info@hanhongsci.com
- Country
- China
- ProdList
- 42982
- Advantage
- 64
- Tel
- 021-50135380
- shchemsky@sina.com
- Country
- China
- ProdList
- 32344
- Advantage
- 50
- Tel
- 15527768850
- 1791901229@qq.com
- Country
- China
- ProdList
- 8849
- Advantage
- 52
- Tel
- +86 (531) 88811783
- Fax
- +86 (531) 55696010 QQ 1762738062
- sales@trio-pharmatech.com (International market)
- Country
- China
- ProdList
- 1856
- Advantage
- 62
- Tel
- 010-82954736 13391601435
- sales@isomersyn.com
- Country
- China
- ProdList
- 3296
- Advantage
- 57
- Tel
- 400-1166-196 18981987031
- Fax
- 028-84555506 800101999
- cdhxsj@163.com
- Country
- China
- ProdList
- 11726
- Advantage
- 57
- Tel
- 400 638 7771
- sales@heowns.com
- Country
- China
- ProdList
- 14443
- Advantage
- 57
- Tel
- 86-21-63210123
- Fax
- 86-21-63290778 86-21-63218885
- sj_scrc@sinopharm.com
- Country
- China
- ProdList
- 9823
- Advantage
- 79
- Tel
- +8613162137806 18575662672
- Fax
- 021 51613951
- mzeng@3wpharm.com
- Country
- China
- ProdList
- 9747
- Advantage
- 57
- Tel
- 0731-85526065 13308475853
- ivy@hnhbsj.com
- Country
- China
- ProdList
- 4550
- Advantage
- 62
- Tel
- 027-027-59207852 13308628970
- Fax
- QQ3130921841
- buy@fortunachem.com
- Country
- China
- ProdList
- 2893
- Advantage
- 58
- Tel
- 0411-62910999 13889544652
- sales@meilune.com
- Country
- China
- ProdList
- 4647
- Advantage
- 58
- Tel
- 4008-755-333 18080918076
- Fax
- 028-86757656
- 800078821@qq.com
- Country
- China
- ProdList
- 9725
- Advantage
- 55
- Tel
- 86-21-34053660
- Fax
- 86-21-34053661
- sale@labgogo.com
- Country
- China
- ProdList
- 9872
- Advantage
- 52
- Tel
- 800-810-5118
- Fax
- +86-10-84193589
- cnchemical@thermofisher.com
- Country
- China
- ProdList
- 17779
- Advantage
- 75
- Tel
- 010-56205725
- Fax
- 010-65763397
- waley188@sohu.com
- Country
- China
- ProdList
- 12338
- Advantage
- 58
- Tel
- 021-58950125
- Fax
- (86) 21-58955996
- info@chemexpress.com
- Country
- China
- ProdList
- 7553
- Advantage
- 61
- Tel
- 4009209199
- Fax
- 86-021-52271987
- sales@9dingchem.com
- Country
- China
- ProdList
- 22519
- Advantage
- 55
- Tel
- 86 592 2680277
- Fax
- 0086 592 2680237
- sale@simagchem.com
- Country
- China
- ProdList
- 430
- Advantage
- 55
- Tel
- 18521735133 18521732826;
- Fax
- 021-50323701
- market@aladdin-e.com
- Country
- China
- ProdList
- 25015
- Advantage
- 65
- Tel
- 021-61552785
- Fax
- 021-55660885
- sales@shshiji.com
- Country
- China
- ProdList
- 9552
- Advantage
- 55
- Tel
- 020-39119399 18927568969
- Fax
- 020-39119999
- isunpharm@qq.com
- Country
- China
- ProdList
- 4428
- Advantage
- 55
- Tel
- 025-57798810
- Fax
- 025-57019371
- sales@sunlidabio.com
- Country
- China
- ProdList
- 3750
- Advantage
- 55
- Tel
- 021-33632979 15002134094
- Fax
- 021-33632979
- marketing@targetmol.com
- Country
- China
- ProdList
- 7934
- Advantage
- 58
- Tel
- 021-33632979
- Fax
- 021-34692979
- info@tsbiochem.com
- Country
- China
- ProdList
- 8073
- Advantage
- 58
- Tel
- 13971561712, 13995564702, 027-50664929
- Fax
- 027-50664927
- hbeixys2001@163.com
- Country
- China
- ProdList
- 3123
- Advantage
- 55
- Tel
- 0554-2106669
- Fax
- 0554-2666215
- sales1@kedichem.com
- Country
- China
- ProdList
- 4928
- Advantage
- 55
- Tel
- 400-1647117 15221909166
- Fax
- +86-21-61629029
- product02@bidepharm.com
- Country
- China
- ProdList
- 41438
- Advantage
- 60
- Tel
- 021-54359730 400-008-9730
- Fax
- 021-54353864
- info@chemxyz.com
- Country
- China
- ProdList
- 3993
- Advantage
- 60
- Tel
- 028-81700200 18116577057
- Fax
- 028-81705658
- 3003855609@qq.com
- Country
- China
- ProdList
- 7892
- Advantage
- 56
- Tel
- 400-1166-196 13458535857
- Fax
- QQ：800101999
- cdhxsj@163.com
- Country
- China
- ProdList
- 13358
- Advantage
- 58
- Tel
- 0510-85629785 18013409632
- Fax
- 051085625359
- sales@reading-chemicals.com
- Country
- China
- ProdList
- 15185
- Advantage
- 58
- Tel
- 027-87465837 19945049750
- Fax
- 027-8777-2287
- sales@finetechnology-ind.com
- Country
- China
- ProdList
- 9636
- Advantage
- 58
- Tel
- 021-60345187 13671753212
- Fax
- 021-34702061
- lzz841106@aliyun.com
- Country
- China
- ProdList
- 10287
- Advantage
- 55
- Tel
- 15221275939 15221275939
- Fax
- 021-50706099
- shenlinxing@macklin.cn
- Country
- China
- ProdList
- 15878
- Advantage
- 55
- Tel
- 025-66113011 18112977050
- cb6@aikonchem.com
- Country
- China
- ProdList
- 16687
- Advantage
- 50
- Tel
- 021-60455363 18019463053
- Fax
- 50966098
- sales@coolpharm.com
- Country
- China
- ProdList
- 12357
- Advantage
- 58
- Tel
- 027-59599241 18871490274
- Fax
- 027-59599241
- 1400878000@qq.com
- Country
- China
- ProdList
- 9972
- Advantage
- 58
- Tel
- 021-61415566 800-8193336
- orderCN@merckgroup.com
- Country
- China
- ProdList
- 51471
- Advantage
- 80
- Tel
- 027-027-59207879 18140587686
- Fax
- QQ：1972026995
- kf@3600chem.com
- Country
- China
- ProdList
- 4699
- Advantage
- 55
- Tel
- 028-64353063
- Fax
- 028-64353063 QQ:784253935
- reacchemical@163.com
- Country
- China
- ProdList
- 5259
- Advantage
- 58
View Lastest Price from 6-Thioguanine manufacturers
- Product
- 6-Thioguanine 154-42-7
- Price
- US $70.00-10.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 10 tons
- Release date
- 2023-09-22
- Product
- 6-Thioguanine 154-42-7
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%min
- Supply Ability
- 1000kg
- Release date
- 2023-01-13
- Product
- 6-Thioguanine 154-42-7
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2022-10-12