6-AZAURIDINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H11N3O6
Molecular Weight	245.1894
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O

InChI

InChIKey=WYXSYVWAUAUWLD-SHUUEZRQSA-N

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

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
6-Azauridine in combination chemotherapy of childhood acute myelocytic leukemia.	1972 Apr	4552812
Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro.	1989 Sep	2480744
Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.	1997 Sep-Oct	9403935
In vitro metabolism studies of the prodrug, 2',3',5'-triacetyl-6-azauridine, utilizing an automated analytical system.	2001 Dec	11600283
Phosphorylation of uridine and cytidine nucleoside analogs by two human uridine-cytidine kinases.	2001 May	11306702
Antiviral activity and mode of action studies of ribavirin and mycophenolic acid against orthopoxviruses in vitro.	2001 Nov	12018677
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.	2001 Nov 8	11689085
Site specific incorporation of 6-azauridine into the genomic HDV ribozyme active site.	2001 Oct-Nov	11719998
Identification of active antiviral compounds against a New York isolate of West Nile virus.	2002 Jul	12076755
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.	2002 Oct	12367731
Use of nucleotide analogs by class I and class II CCA-adding enzymes (tRNA nucleotidyltransferase): deciphering the basis for nucleotide selection.	2003 Aug	12869708
Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus.	2003 Jun 14	12814717
Interferon, ribavirin, 6-azauridine and glycyrrhizin: antiviral compounds active against pathogenic flaviviruses.	2003 Mar	12719009
A simple assay for determining antiviral activity against Crimean-Congo hemorrhagic fever virus.	2004 Apr	15026198
Comprehensive analysis of risk factors associating with Hepatitis B virus (HBV) reactivation in cancer patients undergoing cytotoxic chemotherapy.	2004 Apr 5	15054446
In vitro inhibition of Chikungunya and Semliki Forest viruses replication by antiviral compounds: synergistic effect of interferon-alpha and ribavirin combination.	2004 Feb	14670584
[Biotechnological synthesis of ribavirin. Effect of ribavirin and its various combinations on the reproduction of Vaccinia virus].	2004 Nov-Dec	15586813
Synthesis of N3-substituted uridine and related pyrimidine nucleosides and their antinociceptive effects in mice.	2005 Mar	15744105
Broad-spectrum inhibitor of viruses in the Flaviviridae family.	2005 Nov	16199098
Azacytidine (Vidaza(R)) in the treatment of myelodysplastic syndromes.	2006 Dec	18360650
6-Azauracil or 8-aza-7-deazaadenine nucleosides and oligonucleotides: the effect of 2'-fluoro substituents and nucleobase nitrogens on conformation and base pairing.	2008 Feb 7	18219432
Structure and inhibition of orotidine 5'-monophosphate decarboxylase from Plasmodium falciparum.	2008 Mar 25	18303855
N-methylisatin-beta-thiosemicarbazone derivative (SCH 16) is an inhibitor of Japanese encephalitis virus infection in vitro and in vivo.	2008 May 22	18498627
Antimicrobial and cytotoxic arylazoenamines. Part III: antiviral activity of selected classes of arylazoenamines.	2008 Sep 15	18760610
Antiviral activity of indole derivatives.	2009 Aug	19445965
Transcript elongation factor TFIIS is involved in arabidopsis seed dormancy.	2009 Feb 27	19150360
Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives.	2009 Jul 1	19482481
Hepatoprotective Activity of Licorice Water Extract against Cadmium-induced Toxicity in Rats.	2009 Jun	18955229
Recognition of acyl donors by lipase CAL-B in the acylation of 6-azauridine.	2009 May-Jun	19452525
Insights into arbovirus evolution and adaptation from experimental studies.	2010 Dec	21994633
Six RNA viruses and forty-one hosts: viral small RNAs and modulation of small RNA repertoires in vertebrate and invertebrate systems.	2010 Feb 12	20169186
Historical perspectives in the development of antiviral agents against poxviruses.	2010 Jun	21994682
Triplet formation of 6-azauridine and singlet oxygen sensitization with UV light irradiation.	2010 May 21	20445916

Patents

Name

Type

Language

6-AZAURIDINE

Systematic Name

English

6-AZAURACIL RIBOSIDE

Common Name

English

6-AZAURIDINE [HSDB]

Common Name

English

6-AZAURIDINE [MI]

Common Name

English

6-AZAURACIL-.BETA.-D-RIBOSIDE

Common Name

English

AZAURIDINE

Systematic Name

English

NSC-32074

Code

English

RIBOAZAURACIL

Common Name

English

AZAURIDINE [MART.]

Common Name

English

6-AZUR

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2170