Basic information
- CAS
54-25-1- Standard SMILES
O=c1cnn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1- InChIKey
WYXSYVWAUAUWLD-SHUUEZRQSA-N- Molecular formula
- C8H11N3O6
- Average molar mass
- 245.19 g/mol
- Monoisotopic mass
- 245.06478507
Overview
6-azauridine is a N-glycosyl-1,2,4-triazine. It has a role as an antimetabolite, an antineoplastic agent and a drug metabolite.
Names & identifiers
- Preferred name
- 6-Azauridine
- IUPAC
- 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazine-3,5-dione
- English name
- 6-AZAURIDINE
- Molecular formula
- C8H11N3O6
- Molecular weight
- 245.19
Names & synonyms
6-AZAURIDINE54-25-1AzauridineRiboazauracil6-Azur6-Azauracil ribosideAzUR6-Azauracil 1-riboside6-Azauracilriboside2-beta-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione6-Azauracil-beta-D-ribosideNSC 32074
Show more names
6-azuridine2-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1,2,4-triazine-3,5(2H,4H)-dionensc32074AZURIDINEAids008706Aids-008706
7BVB29RCPR2beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione3,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine riboside1,2,4-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-NSC-320742-beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dioneas-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-CHEBI:35668
Database identifiers
- CAS
54-25-1- PubChem CID
- 5901
- DTXSID
DTXSID20960091- ChEMBL
CHEMBL564201
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 132 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 372
Experimental & physicochemical properties
SpringerMaterials PropertiesCrystal structure
LogP
log Kow = -2.14
-2.14
Color/FormCrystals from ether, ethanol
Solubility
Soluble in water
36.2 [ug/mL] (The mean of the results at pH 7.4)
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxide/.
Melting Point158 °C
Optical RotationMax absorption (water): 262 nm (e= 6100); specific optical rotation: -132 deg at 24 °C/D (pyridine)
Dissociation Constants
pKa = 6.63
pKa: 6.7 /Triacetyl deriv/
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety & protection
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Toxicology
Interactions
Chemistry & industry
Pharmacology
Mechanism of Action
6-Azauridine (AzUrd) is a broad-spectrum antimetabolite that inhibits both DNA and RNA virus multiplication. Prior work indicated that several AzUrd-sensitive viruses induced an increase in the level of uridine kinase, and this might explain the selective activity of AzUrd on such viruses. Present studies compared AzUrd sensitive and resistant viruses with respect to their orotic acid pathways by labeling cells with [14C]-orotic acid during the latent period of viral infection. No differences were detected by this method with either vaccinia, Newcastle disease, or vesicular stomatitis viruses. AzUrd inhibits transport of orotic acid into the cell by 30%, while incorporation of orotic acid into cellular RNA is inhibited by 50% (taking into consideration the 30% already noted) when the highest concentration of antimetabolite is used. This suggests that, in addition to blocking orotidylic acid decarboxylase, AzUrd may act on some other site (sites) of action in the inhibition of virus multiplication.
... pyrazofurin and 6-azauridine, two nucleoside analogues that are assumed to interfere with OMP decarboxylase, another enzyme involved in the biosynthesis of pyrimidine ribonucleotides, potentiate the cytocidal activity of Ce-Cyd.
Azacitidine is readily deaminated to azauridine and further degraded. It is incorporated into DNA and alters gene expression. ... Azacitidine causes hypomethylation of DNA both in vivo and in vitro.
Biological Half-Life
After absorption, azaribine is almost entirely deacetylated to azur /azauridine/ in blood, with some monoacetyl deriv detectable. Peak plasma concn of azur are reached after 2 to 4 hr, and plasma disappearance curve with half-time of approx 6 to 8 hr is observed. /6-Azauridine triacetyl deriv/
Metabolism/Metabolites
L1210 cells... incubated with /6-azauridine/ AzUrd contained a new 254 nm-absorbing component, not found in control cells. It appeared to be 6-azauridine-5'-triphosphate, since it was the only peak in the triphosphate region of the chromatogram which contained 3H after incubation of cells with [3H]AzUrd.
... Azauridine is metabolized to azauracil by intestinal micoorganism ...
Azauridine undergoes intracellular conversion to 6-azauridylic acid ... /6-Azauridine triacetyl deriv/
After oral administration about 45 per cent of 2',3',5'-tri-O-acetyl-6-azauridine (TA-6-azauridine) is eliminated in the urine of rats, as well as in man, in the form of its deacetylation products. In the urine of rats, TA-6-azauridine is excreted almost exclusively in the form of free 6-azauridine whereas in man a substantial amount of mono-O-acetyl-azauridine (MA-6-azauridine) also was found. Furthermore, about 35 per cent of the dose was found in the form of MA-6-azauridine in the feces of rats collected during 48 hr after the administration. Neither TA-6-azauridine nor its deacetylation products are excreted in the bile of rats. 6-Azauracil was not detected as a deribosylation product of 6-azauridine neither in the urine or feces nor in the bile of rats under study. /6-Azauridine triacetyl deriv/
Related reactions
1 records
Compound notes
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