Tiazofurin

Names

[ Name ]:
Tiazofurin

[Synonym ]:
(1R)-1,4-Anhydro-1-(4-carbamoyl-1,3-thiazol-2-yl)-D-ribitol
Riboxamide
D-Ribitol, 1-C-[4-(aminocarbonyl)-2-thiazolyl]-1,4-anhydro-, (1R)-
2-b-D-Ribofuranosyl-4-thiazolecarboxamide
Tiazofurina [Spanish]
4-Thiazolecarboxamide, 2-β-D-ribofuranosyl-
2-β-D-Ribofuranosyl-4-thiazolecarboxamide
[3H]-Tiazofurin
Tiazofurine
Tiazole
Tiazofurin
Tiazofurina
Tiazofurinum
2-β-D-Ribofuranosylthiazole-4-carboxamide
Tiazofurinum [Latin]

Biological Activity

[Description]:

Tiazofurin is a synthetic nucleoside analogue with antineoplastic activity. Tiazofurin is anabolized intracellularly to tiazole-4-carboxamide adenine dinucleotide (TAD), a potent inhibitor of IMP dehydrogenase (IMPDH).

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

[References]

[1]. Tricot G, Jayaram HN, Weber G, Hoffman R. Tiazofurin: biological effects and clinical uses. Int J Cell Cloning. 1990;8(3):161-170.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
641.3±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₉H₁₂N₂O₅S

[ Molecular Weight ]:
260.267

[ Flash Point ]:
341.6±31.5 °C

[ Exact Mass ]:
260.046692

[ PSA ]:
154.14000

[ LogP ]:
-1.13

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.675

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XJ3600000

CHEMICAL NAME :: 4-Thiazolecarboxamide, 2-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 60084-10-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C9-H12-N2-O5-S

MOLECULAR WEIGHT :: 260.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 1135 mg/kg/15D-I

TOXIC EFFECTS :: Behavioral - headache Musculoskeletal - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 892 mg/kg/10D-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1684 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3400 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Blood - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1090 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Behavioral - fluid intake

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 3425 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 20 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,5512,1985

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2934100090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934100090

[ Summary ]:
2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%