Azaribine

Chemical compound From Wikipedia, the free encyclopedia

Azaribine (triacetyl-6-azauridine) is a drug developed by Calbiochem for the treatment of psoriasis,[1][2] and also has anti-cancer and antiviral actvities.[3][4] It is a prodrug which is metabolised to the nucleoside analogue 6-azauridine in the body.[5]

Trade namesTriazure
Legal status
  • US: Withdrawn
Quick facts Clinical data, Trade names ...
Azaribine
Clinical data
Trade namesTriazure
Legal status
Legal status
  • US: Withdrawn
Identifiers
  • [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(3,5-dioxo-1,2,4-triazin-2-yl)oxolan-2-yl]methyl acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.832 Edit this at Wikidata
Chemical and physical data
FormulaC14H17N3O9
Molar mass371.302 g·mol−1
3D model (JSmol)
  • CC(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C(=O)NC(=O)C=N2)OC(=O)C)OC(=O)C
  • 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
  • Key:QQOBRRFOVWGIMD-OJAKKHQRSA-N
Close

Azaribine received FDA approval in 1975 for the treatment of severe psoriasis,[2][6][7] but was subsequently withdrawn from the market in 1976 (with its New Drug Application formally revoked in 1977[8]), following reports of life-threatening thromboembolic events.[2][5] These side effects, including both arterial and venous thrombosis, is primarily attributed to azaribine acting as a vitamin B6 antagonist, which induces a severe functional deficiency of pyridoxal phosphate and the resultant hyperhomocysteinemia.[5][9][10][11] However, it continues to be researched as a potential agent for the treatment of emerging viral diseases.[12]

References

Related Articles

Wikiwand AI