6-AZAURIDINE 2',3',5'-TRIACETATE

Modify Date: 2024-01-03 16:12:14

6-AZAURIDINE 2',3',5'-TRIACETATE Structure
6-AZAURIDINE 2',3',5'-TRIACETATE structure
Common Name 6-AZAURIDINE 2',3',5'-TRIACETATE
CAS Number 2169-64-4 Molecular Weight 371.29900
Density 1.6g/cm3 Boiling Point N/A
Molecular Formula C14H17N3O9 Melting Point 99-101ºC(lit.)
MSDS N/A Flash Point N/A

 Use of 6-AZAURIDINE 2',3',5'-TRIACETATE


Azaribine (2',3',5'-Tri-O-acetyl-6-azauridine) is a potent orotidine monophosphate decarboxylase (OMPD) inhibitor. Azaribine is an antiviral inhibitor of several RNA viruses and inhibits viral genome replication and gene transcription. Azaribine shows broad-spectrum antiviral activity (EC50=3.80 nM-1.73 μM against influenza A and B viruses; EC50=1.62 μM against ZIKV Paraiba). Azaribine, a triacetate salt of Azauridine, has the potential for psoriasis research[1][2].

 Names

Name 6-azauridine 2',3',5'-triacetate
Synonym More Synonyms

 6-AZAURIDINE 2',3',5'-TRIACETATE Biological Activity

Description Azaribine (2',3',5'-Tri-O-acetyl-6-azauridine) is a potent orotidine monophosphate decarboxylase (OMPD) inhibitor. Azaribine is an antiviral inhibitor of several RNA viruses and inhibits viral genome replication and gene transcription. Azaribine shows broad-spectrum antiviral activity (EC50=3.80 nM-1.73 μM against influenza A and B viruses; EC50=1.62 μM against ZIKV Paraiba). Azaribine, a triacetate salt of Azauridine, has the potential for psoriasis research[1][2].
Related Catalog
In Vitro Azaribine (2',3',5'-Tri-O-acetyl-6-azauridine; 0-2 μM; 48 小时) 对MDCK细胞具有细胞毒性 (MTT: CC50=19.66 μM)[1]。 Azaribine 对 BIRFLU 增殖具有强效抑制作用 (MDCK 细胞: EC50=0.29 μM;A549 细胞: EC50=0.55 μM) [1]。 Azaribine 在 MDCK 细胞后处理期间显示出对季节性 H1N1 和 H3N2 IAV 和 IBV 的抑制作用,EC50 分别为 0.60 μM、0.77 μM、0.80 μM[1]。 Azaribine 在 16HBE 细胞的后处理过程中具有抗 NC H1N1 作用,EC50 为 1.58 μM[1]。 Cell Cytotoxicity Assay[1] Cell Line: MDCK cells Concentration: 0-2 μM Incubation Time: 48 h Result: Had cytotoxicity on MDCK cells (CC50=19.66 μM).
References

[1]. Jun-Gyu Park, et al. Identification and Characterization of Novel Compounds with Broad-Spectrum Antiviral Activity against Influenza A and B Viruses. J Virol. 2020 Mar 17;94(7):e02149-19.  

[2]. Desarey Morales Vasquez, et al. Identification of Inhibitors of ZIKV Replication. Viruses. 2020 Sep 18;12(9):1041.  

 Chemical & Physical Properties

Density 1.6g/cm3
Melting Point 99-101ºC(lit.)
Molecular Formula C14H17N3O9
Molecular Weight 371.29900
Exact Mass 371.09600
PSA 155.88000
Index of Refraction 1.621

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XY8577000
CHEMICAL NAME :
as-Triazine-3,5-(2H,4H)-dione, 2-(2',3',5'-triacetyl-beta-D-ribofuranosyl)-
CAS REGISTRY NUMBER :
2169-64-4
LAST UPDATED :
199612
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C14-H17-N3-O9
MOLECULAR WEIGHT :
371.34
WISWESSER LINE NOTATION :
T6NNVMVJ B- CT5OTJ BOV1 DOV1 E1OV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
5670 mg/kg/6W
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Blood - changes in cell count (unspecified)
REFERENCE :
AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 108,272,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
321 gm/kg/15W-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in erythrocyte (RBC) count Related to Chronic Data - death
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - pig
DOSE/DURATION :
30 gm/kg/14W-I
TOXIC EFFECTS :
Blood - changes in erythrocyte (RBC) count
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970

 Safety Information

Safety Phrases S22-S24/25
WGK Germany 2
RTECS XY8577000

 Precursor & DownStream

Precursor  2

DownStream  1

 Synonyms

EINECS 218-515-6
6-AZURD-TA
6-azauridine-2',3',5'-tri-O-acetate
triacetyl-6-azauridine
ta-azur
cb304
2',3',5'-TRI-O-ACETYL-6-AZAURIDINE
AZARIBINE
2',3',5'-triacetyl-6-azauridine