6-Azathymine

Names

[ CAS No. ]:
932-53-6

[ Name ]:
6-Azathymine

[Synonym ]:
6-Methyl-2H-[1,2,4]triazin-3,5-dion
USAF CB-28
1,2,4-triazine-3,5-diol, 6-methyl-
Azathymine
6-methyl-2H-[1,2,4]triazine-3,5-dione
Azathymine,6
6-azathymine
1,2,4-Triazine-3,5(2H,4H)-dione,6-methyl
6-methyl-2H-[1,2,4]triazin-3,5-dione
6-methyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione
6-Methyl-1,2,4-triazine-3,5(2H,4H)-dione
6-methyl-1,2,4-triazine-3,5-diol
5-Methyl-6-azauracil
MFCD00006457
1,2,4-Triazine-3,5(2H,4H)-dione, 6-methyl-
EINECS 213-253-9

Biological Activity

[Description]:

6-Azathymine, a 6-nitrogen analog of thymine, is a potent D-3-aminoisobutyrate-pyruvate aminotransferase inhibitor. 6-Azathymine inhibits the biosynthesis of DNA, and has antibacterial and antiviral activities[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

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

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

6-Azathymine is a competitive antagonist of the growth of Streptococcus faecalis (8043) and several other strains of microorganisms. Studies of the mechanism of action of 6-Azathymine reveal that S. faecalis can convert the analog to the corresponding deoxyriboside, azathymidine[2].

[References]

[1]. N Tamaki, et al. Purification, Characterization and Inhibition of D-3-aminoisobutyrate Aminotransferase From the Rat Liver. Eur J Biochem. 1990 Apr 20;189(1):39-45.

[2]. W H PRUSOFF, et al. Effect of the Deoxyriboside of 6-azathymine (Azathymidine) on the Biosynthesis of Deoxyribonucleic Acid by Bone Marrow and Neoplastic Cells (In Vitro). Biochim Biophys Acta. 1956 Apr;20(1):209-14.

[3]. R A GAITO, et al. Studies on the Metabolism of Thymine and 6-azathymine. Biochem Pharmacol. Apr-May 1962;11:323-36.

[4]. B. Gabrielsen, et al. In vitro and in vivo antiviral (RNA) evaluation of orotidine 51-monophosphatedecarboxylase inhibitors and analogues including 6-azauridine-51-(ethylmethoxyalaninyl)phosphate (a 51-monophosphate prodrug). Antiviral Chemistry & Chemotherapy (1994) 5(4), 209-220.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Melting Point ]:
210-212°C

[ Molecular Formula ]:
C₄H₅N₃O₂

[ Molecular Weight ]:
127.101

[ Exact Mass ]:
127.038177

[ PSA ]:
78.61000

[ LogP ]:
-2.05

[ Index of Refraction ]:
1.692

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XY8050000

CHEMICAL NAME :: as-Triazine-3,5(2H,4H)-dione, 6-methyl-

CAS REGISTRY NUMBER :: 932-53-6

LAST UPDATED :: 199012

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C4-H5-N3-O2

MOLECULAR WEIGHT :: 127.12

WISWESSER LINE NOTATION :: T6NMVMVJ F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1800 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage)

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 95,123,1953

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD277-689

Safety Information

[ Safety Phrases ]:
S22-S24/25

[ RTECS ]:
XY8050000

[ HS Code ]:
2933699090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933699090

[ Summary ]:
2933699090 other compounds containing an unfused triazine ring (whether or not hydrogenated) in the structure。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:20.0%