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Substance Name: Azaribine [USAN:INN:BAN]
RN: 2169-64-4
UNII: K1U80DO9EB
InChIKey: QQOBRRFOVWGIMD-OJAKKHQRSA-N

Note

  • Pyrimidine analogue; anti-metabolite used in psoriasis & mycosis fungoides.

Molecular Formula

  • C14-H17-N3-O9

Molecular Weight

  • 371.3003
 

Classification Codes

  • Antipsoriatic
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Azaribine
  • Azaribine [USAN:INN:BAN]

Synonyms

  • 2',3',5'-Tri-O-acetyl-6-azauridine
  • 2',3',5'-Triacetyl-6-azauridine
  • 2-(2',3',5'-Triacetyl-beta-D-ribofuranosyl)-as-triazine-3,5-(2H,4H)-dione
  • 2-(beta-D-ribofuranosyl)-1,2,4-triazin-3,5(2H,4H)-dion 2',3',5'-triacetat
  • 2-beta-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione 2',3',5'-triacetate
  • 6-Azauracilribosid-triacetat
  • 6-Azauridin-triacetat
  • 6-Azauridine 2',3',5'-triacetate
  • 6-AzUR TA
  • 6-AzUR-TA
  • AI3-52937
  • as-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-, triacetate
  • Azaribin
  • Azaribina
  • Azaribina [INN-Spanish]
  • Azaribine
  • Azaribinum
  • Azaribinum [INN-Latin]
  • Azauridine triacetate
  • AZR
  • BRN 0631776
  • CB 304
  • EINECS 218-515-6
  • NSC 67239
  • NSC-67239
  • SKI 28426
  • TA-Azur
  • Triacetyl-6-azauridine
  • Triacetyl-6-azuridine
  • Triazure
  • UNII-K1U80DO9EB

Systematic Names

  • 1,2,4-Triazine-3,5(2H,4H)-dione, 2-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-
  • as-Triazine-3,5(2H,4H)-dione, 2-beta-D-ribofuranosyl-, 2',3',5'-triacetate (8CI)
  • as-Triazine-3,5-(2H,4H)-dione, 2-(2',3',5'-triacetyl-beta-D-ribofuranosyl)-
  • Azaribine

Registry Numbers

CAS Registry Number

  • 2169-64-4

FDA UNII

  • K1U80DO9EB

System Generated Number

  • 0002169644

Structure Descriptors

InChI

1S/C14H17N3O9/c1-6(18)23-5-9-11(24-7(2)19)12(25-8(3)20)13(26-9)17-14(22)16-10(21)4-15-17/h4,9,11-13H,5H2,1-3H3,(H,16,21,22)/t9-,11-,12-,13-/m1/s1

InChIKey

QQOBRRFOVWGIMD-OJAKKHQRSA-N

Smiles

CC(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2c(=O)[nH]c(=O)cn2)OC(=O)C)OC(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 5670mg/kg/6W (5670mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
American Journal of Obstetrics and Gynecology. Vol. 108, Pg. 272, 1970.
mouse LD50 oral 7800mg/kg (7800mg/kg)   Toxicology and Applied Pharmacology. Vol. 17, Pg. 511, 1970.
rat LD50 oral 12gm/kg (12000mg/kg)   Toxicology and Applied Pharmacology. Vol. 17, Pg. 511, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 99-101 deg C   EXP
log P (octanol-water) -0.2 (none)   EXP
Water Solubility 334 mg/L 25 EST
Vapor Pressure 1.60E-12 mm Hg 25 EST
Henry's Law Constant 1.72E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.11E-11 cm3/molecule-sec 25 EST

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