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About This Item
Empirical Formula (Hill Notation):
C8H11N3O6
CAS Number:
Molecular Weight:
245.19
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
Assay
≥99% (TLC)
Quality Level
form
powder
mp
157-159 °C (lit.)
solubility
water: 50 mg/mL, clear, colorless
storage temp.
2-8°C
SMILES string
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O
InChI
1S/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)/t3-,5-,6-,7-/m1/s1
InChI key
WYXSYVWAUAUWLD-SHUUEZRQSA-N
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General description
6-Azauridine is a pyrimidine nucleoside analog.
Application
6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.
6-Azauridine has been used:
- in uridine monophosphate synthase (UMPS) activity assay
- as an antiviral agent to study its inhibition effect and cytotoxic potential on foot and mouth disease virus
- to screen for anticryptosporidial activity
- in the pretreatment of HeLa cells to study its effect on inhibition of cellular uridine synthesis before and during chase with 5-bromouridine 5′-triphosphate (BrUTP)
- as a reference compound for comparing the antiviral activity and cytotoxic activity against viral host cell lines
Biochem/physiol Actions
6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS). It is a broad spectrum anti-metabolite. It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a antineoplastic metabolite. It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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