6-Thioguanine
- Iupac Name：2-amino-3,7-dihydropurine-6-thione
- CAS No.: 154-42-7
- Molecular Weight：167.19
- Modify Date.: 2022-11-05 04:30
- Introduction: 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.
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1. Names and Identifiers
- 1.1 Name
- 6-Thioguanine
- 1.2 Synonyms
2-Amino-1,7-dihydro-6H-purine-6-thione 2-Amino-1H-purine-6(7H)-thione 2-AMINO-6-MERCAPTOPURINE 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol 2-Amino-6-mercaptopurine,2-Amino-6-purinethiol 2-Amino-6-methoxy purine 2-AMINO-6-PURINETHIOL 2-amino-9H-purine-6(1H)-thione 2-aminomercaptopurine 2-amino-purine-6(1h)-thion 2-aminopurine-6(1h)-thione 5'-ribonucleotide 6-Mercaptoguanine 6-tg 6-thioguanidine 7H-Purine-6-thiol, 2-amino- bw5071 complex coenzyme dibutyryl cyclic AMP calcium salt EINECS 205-827-2 lanvis MFCD00233553 tabloid Tg thio-guanin thioguanine tioguanin Tioguanine wellcomeu3b
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- 1.3 CAS No.
- 154-42-7
- 1.4 CID
- 2723601
- 1.5 EINECS(EC#)
- 205-827-2
- 1.6 Molecular Formula
- C5H5N5S (isomer)
- 1.7 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)
- 1.8 InChIkey
- WYWHKKSPHMUBEB-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=NC2=C(N1)C(=S)N=C(N2)N
- 1.10 Isomers Smiles
- C1=NC2=C(N1)C(=S)N=C(N2)N
2. Properties
- 2.1 Density
- 1.483 (estimate)
- 2.1 Melting point
- ≥300 °C(lit.)
- 2.1 Boiling point
- 123 (29 torr)
- 2.1 Refractive index
- 1.5605 (estimate)
- 2.1 Flash Point
- 356°C
- 2.1 Precise Quality
- 167.02700
- 2.1 PSA
- 119.28000
- 2.1 logP
- 0.80500
- 2.1 Appearance
- Odorless or almost odorless pale yellow crystalline powder.
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- Crystalline, lyophilized, sterile, endot
- 2.4 Color/Form
- Yellow to green
- 2.5 pKa
- pKa 8.22 (Uncertain)
- 2.6 Water Solubility
- soluble
- 2.7 Spectral Properties
- IR: 3:1292H (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 8:110D (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
- 2.8 Stability
- Stable under normal temperatures and pressures.
- 2.9 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine.
- 3.2 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.
- 3.3 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
- 3.4 Usage
- antineoplastic, purine antimetabolite
4. Safety and Handling
- 4.1 Symbol
- GHS06
- 4.1 Hazard Codes
- T,Xi
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- 25-23/24/25
- 4.1 Safety Statements
- 28-36/37/39-45-28A
- 4.1 Exposure Standards and Regulations
- The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl thioguanine, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
- 4.2 Packing Group
- III
- 4.2 Octanol/Water Partition Coefficient
- Log Kow = -0.07
- 4.3 Fire Hazard
- Flash point data for 6-Thioguanine are not available; however, 6-Thioguanine is probably combustible.
- 4.4 Hazard Class
- 6.1
- 4.4 Hazard Declaration
- H301
- 4.4 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.5 RIDADR
- UN 2811 6.1/PG 3
- 4.5 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.
- 4.6 Caution Statement
- P301 + P310
- 4.6 Formulations/Preparations
- Refined grades
- 4.7 WGK Germany
- 3
- 4.7 RTECS
- UP0740000
- 4.7 Toxicity
-
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- UP0740000
- CHEMICAL NAME :
- Purine-6(1H)-thione, 2-amino-
- CAS REGISTRY NUMBER :
- 154-42-7
- LAST UPDATED :
- 199807
- DATA ITEMS CITED :
- 32
- MOLECULAR FORMULA :
- C5-H5-N5-S
- MOLECULAR WEIGHT :
- 167.21
- WISWESSER LINE NOTATION :
- T56 BNM FYM INJ FUS HZ
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- Standard Draize test
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Human
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 160 mg/kg
- TOXIC EFFECTS :
- Gastrointestinal - other changes
Blood - hemorrhage
Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 54 mg/kg
- TOXIC EFFECTS :
- Gastrointestinal - other changes
Blood - hemorrhage
Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- LD10 - Lethal Dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1600 mg/kg
- TOXIC EFFECTS :
- Blood - changes in bone marrow (not otherwise specified)
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 23720 ug/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - conjunctive irritation
Lungs, Thorax, or Respiration - dyspnea
Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 55990 ug/kg/5D-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain
Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 56 mg/kg/2W-I
- TOXIC EFFECTS :
- Blood - normocytic anemia
Blood - changes in leukocyte (WBC) count
Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 650 mg/kg/26W-I
- TOXIC EFFECTS :
- Blood - changes in erythrocyte (RBC) count
Blood - changes in leukocyte (WBC) count
Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 46500 ug/kg/5D-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain
Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 19950 ug/kg/4D-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain
Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 23700 ug/kg/13D-I
- TOXIC EFFECTS :
- Gastrointestinal - ulceration or bleeding from large intestine
Nutritional and Gross Metabolic - body temperature increase
Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 5700 ug/kg/13D-I
- TOXIC EFFECTS :
- Gastrointestinal - ulceration or bleeding from large intestine
Nutritional and Gross Metabolic - body temperature increase
Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 25 mg/kg
- SEX/DURATION :
- female 12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - extra-embryonic structures
(e.g., placenta, umbilical cord)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 10 mg/kg
- SEX/DURATION :
- female 7 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
resorbed implants per total number of implants)
- TYPE OF TEST :
- Cytogenetic analysis
MUTATION DATA
- TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 15 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE
Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 139,149,1984
*** REVIEWS ***
TOXICOLOGY REVIEW
32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York,
Springer, 1975 Volume(issue)/page/year: -,49,1975
*** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA ***
NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA :
NOES - National Occupational Exposure Survey (1983)
NOES Hazard Code - X5676
No. of Facilities: 18 (estimated)
No. of Industries: 1
No. of Occupations: 2
No. of Employees: 82 (estimated)
No. of Female Employees: 27 (estimated)
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5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H301 Toxic if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
154-42-7Total: 2 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,9337
- 9.1 BRN
- 157765
- 9.2 Description
- 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.
- 9.3 Chemical Properties
- Crystalline, lyophilized, sterile, endot
- 9.4 Originator
- Thioguanine,Burroughs-Wellcome,US,1966
- 9.5 Uses
- antineoplastic, purine antimetabolite
- 9.6 Uses
- The compound produced dose-dependent inhibition of stimulated expression of TRAIL protein
- 9.7 Uses
- Thioguanine USP (Tabloid)is used to treat acute leukemia; chronic granulocytic leukemia.
- 9.8 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. - View all
- 9.9 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.
- 9.10 Definition
- ChEBI: A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine.
- 9.11 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.
- 9.12 Brand name
- Tioguanine is INN and BAN.
- 9.13 Therapeutic Function
- Cancer chemotherapy
- 9.14 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.
- 9.15 General Description
- Odorless or almost odorless pale yellow crystalline powder.
- 9.16 Air & Water Reactions
- 6-Thioguanine may be sensitive to prolonged exposure to air. Insoluble in water.
- 9.17 Reactivity Profile
- 6-Thioguanine is incompatible with strong oxidizing agents. .
- 9.18 Fire Hazard
- Flash point data for 6-Thioguanine are not available; however, 6-Thioguanine is probably combustible.
- 9.19 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.
- 9.20 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.
- 9.21 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.
- 9.22 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.
- 9.23 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.
- 9.24 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).
- 9.25 Veterinary Drugs and Treatments
- Thioguanine may be useful as adjunctive therapy for acute lymphocytic or granulocytic leukemia in dogs or cats.
- 9.26 Usage
- 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.
- 9.27 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.]
10. Computational chemical data
- Molecular Weight: 167.19g/mol
- Molecular Formula: C5H5N5S
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 167.02656635
- Monoisotopic Mass: 167.02656635
- Complexity: 225
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 111
- Heavy Atom Count: 11
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBjgABAAAAAAAAAAAAAAAAAAWAAAAAgAAAAAAAAAEABgAAAHAQQAAAACAgBVgQFsBbJkACkAQZhZACAgC2REKABUYAoVACASABASAAUAAAIAAJAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
6-Thioguanine for injection is a prescription drug that cannot be purchased at pharmacies or online stores. It can only be prescribed and used in hospitals when needed. Many people have limited knowle..
-
6-Thioguanine (THIOGUANINE) is an anti-tumor drug developed by BurroughsWalcome in 1954, mainly used for the treatment of acute lymphocytic leukemia. The preparation method of 6-Thioguanine was first ..
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