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154-42-7

154-42-7 structure
154-42-7 structure
  • Name: 6-Thioguanine
  • Chemical Name: tioguanine
  • CAS Number: 154-42-7
  • Molecular Formula: C5H5N5S
  • Molecular Weight: 167.192
  • Catalog: API Antineoplastic agents Antimetabolite antineoplastic
  • Create Date: 2018-04-16 08:00:00
  • Modify Date: 2024-01-04 15:06:53
  • 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively.
Name tioguanine
Synonyms MFCD00233553
2-Amino-6-methoxy purine
tabloid
2-aminomercaptopurine
2-amino-9H-purine-6(1H)-thione
tioguanin
2-Amino-6-purinethiol
bw5071
Tioguanine
2-Amino-6-mercaptopurine,2-Amino-6-purinethiol
7H-Purine-6-thiol, 2-amino-
2-Amino-6-mercaptopurine
2-Amino-1H-purine-6(7H)-thione
6-Thioguanine
lanvis
Tg
6-tg
thioguanine
thio-guanin
6-thioguanidine
EINECS 205-827-2
wellcomeu3b
2-Amino-1,7-dihydro-6H-purine-6-thione
6-Mercaptoguanine
Description 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively.
Related Catalog
Target

IC50: 25 μM (PLpros), 40 μM (Recombinant human USP2)[3]

In Vitro 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively[1]. 6-Thioguanine affects the methylation of cytosine residues by purified DNA methyltransferases including human DNMT1 and bacterial HpaII methylase. 6-Thioguanine (1 or 3 μM) decreases global cytosine methylation in Jurkat T cells and cytosine methylation in human cells at 3 μM[2]. 6-Thioguanine (18.75, 37.50, or 75.00 μM) adversely affects cell viability, but with no effect on LDH or ALT activity[3].
Cell Assay Treatments consists of 3 thiopurines (azathioprine, 6-mercaptopurine, and 6-thioguanine) at each of 6 concentrations (0.468, 0.937, 1.875, 3.750, 7.500, and 15.000 μM). Each thiopurinee is dissolved in DMSO solution to achieve a concentration of 10 mg/mL. Sterile filtered maintenance medium is used to further dilute each thiopurine solution to each of the 6 treatment concentrations. Twenty-four hours after the hepatocytes are plated on 96-well culture[3].
References

[1]. Chuang SJ, et al. 6-Thioguanine is a noncompetitive and slow binding inhibitor of human deubiquitinating protease USP2. Sci Rep. 2018 Feb 15;8(1):3102.

[2]. Wang H, et al. 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. 2009 Mar 17;48(10):2290-9.

[3]. LaDuke KE, et al. Effects of azathioprine, 6-mercaptopurine, and 6-thioguanine on canine primary hepatocytes. Am J Vet Res. 2015 Jul;76(7):649-55.
Density 2.1±0.1 g/cm3
Boiling Point 460.7±37.0 °C at 760 mmHg
Melting Point ≥300 °C(lit.)
Molecular Formula C5H5N5S
Molecular Weight 167.192
Flash Point 232.4±26.5 °C
Exact Mass 167.026566
PSA 119.28000
LogP -0.99
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 2.071
Water Solubility soluble

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)
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic;
Risk Phrases R25
Safety Phrases S28-S36/37/39-S45-S28A
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS UP0740000
Packaging Group III
Hazard Class 6.1
HS Code 2933990090
73-40-5 structure

73-40-5

~78%

154-42-7 structure

154-42-7

Literature: Tomsons, U. A.; Avots, A. A.; Kolesnikova, I. A. Pharmaceutical Chemistry Journal, 1985 , vol. 19, # 2 p. 136 - 138 Khimiko-Farmatsevticheskii Zhurnal, 1985 , vol. 19, # 2 p. 206 - 209
3056-33-5 structure

3056-33-5

~%

154-42-7 structure

154-42-7

Literature: Pharmaceutical Chemistry Journal, , vol. 19, # 2 p. 136 - 138 Khimiko-Farmatsevticheskii Zhurnal, , vol. 19, # 2 p. 206 - 209
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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