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Substance Name: 6-Azauridine
RN: 54-25-1
UNII: 7BVB29RCPR
InChIKey: WYXSYVWAUAUWLD-SHUUEZRQSA-N

Note

  • A triazine nucleoside used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic.

Molecular Formula

  • C8-H11-N3-O6

Molecular Weight

  • 245.19
 

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic Agents
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • 6-Azauridine
  • Azauridine

MeSH Heading

  • Azauridine

Synonyms

  • 1,2,4-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-
  • 2-beta-D-Ribofuranosyl-1,2,4-triazin-3,5(2H,4H)-dion
  • 2-beta-D-Ribofuranosyl-1,2,4-triazin-3,5(2H,4H)-dion [Czech]
  • 2-beta-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione
  • 2-beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione
  • 2beta-D-Ribofuranosyl-1,2,4-triazine-3,5-(2H,4H)-dione
  • 2beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione
  • 3,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine riboside
  • 4-26-00-00554 (Beilstein Handbook Reference)
  • 6-Azauracil 1-riboside
  • 6-Azauracil riboside
  • 6-Azauracil-beta-D-riboside
  • 6-Azauracilribosid
  • 6-Azauracilribosid [Czech]
  • 6-Azauracilriboside
  • 6-Azauridine
  • 6-Azur
  • 6-Azuridine
  • AI3-50104
  • as-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-
  • as-Triazine-3,5(2H,4H)-dione, 2beta-D-ribofuranosyl-
  • Azauridine
  • AzUR
  • BRN 0032281
  • EINECS 200-199-6
  • HSDB 3206
  • NSC 32074
  • Ribo-azuracil
  • Riboazauracil
  • Riboazauratsil
  • UNII-7BVB29RCPR

Systematic Names

  • 1,2,4-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-
  • 2-(beta-D-Ribofuranosyl)-1,2,4-triazine-3,5-diol
  • as-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-
  • Azauridine

Superlist Name

  • 6-Azauridine

Registry Numbers

CAS Registry Number

  • 54-25-1

FDA UNII

  • 7BVB29RCPR

Other Registry Number

  • 39455-15-7

System Generated Number

  • 0000054251

Structure Descriptors

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

InChIKey

WYXSYVWAUAUWLD-SHUUEZRQSA-N

Smiles

n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c([nH]c(=O)cn1)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intraperitoneal 2400mg/kg (2400mg/kg)   Biochemical Pharmacology. Vol. 14, Pg. 1537, 1965.
dog LD50 intraperitoneal 3400mg/kg (3400mg/kg)   Biochemical Pharmacology. Vol. 14, Pg. 1537, 1965.
mouse LD50 intraperitoneal 11250mg/kg (11250mg/kg)   Biochemical Pharmacology. Vol. 14, Pg. 1517, 1965.
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 intraperitoneal 9400mg/kg (9400mg/kg)   Teratology, The International Journal of Abnormal Development. Vol. 4, Pg. 287, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 158 deg C   EXP
pKa Dissociation Constant 6.63 (none)   EXP
log P (octanol-water) -2.14E+00 (none)   EXP
Water Solubility 8.28E+04 mg/L 25 EST
Vapor Pressure 6.82E-16 mm Hg 25 EST
Henry's Law Constant 6.23E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.07E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.