Azaribine

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  • US: Withdrawn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

Azaribine (triacetyl-6-azauridine) is a drug developed by Calbiochem for the treatment of psoriasis, and also has anti-cancer and antiviral activities. It is a prodrug which is metabolised to the nucleoside analogue 6-azauridine in the body.

Azaribine received FDA approval in 1975 for the treatment of severe psoriasis, but was subsequently withdrawn from the market in 1976 (with its New Drug Application formally revoked in 1977), following reports of life-threatening thromboembolic events.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

References

  1. ↑ Elis J, Rasková H (March 1972). "New indications for 6-azauridine treatment in man. A review". European Journal of Clinical Pharmacology. 4 (2): 77–81. doi:10.1007/bf00562501. PMID 4570456. S2CID 11005976.
  2. 1 2 3 Shubin S (1979). "Triazure and public drug policies". Perspectives in Biology and Medicine. 22 (2 Pt 1): 185–204. PMID 582335. Retrieved 2026-04-06.
  3. ↑ Creasey WA, Fink ME, Handschumacher RE, Calabresi P (March 1963). "Clinical and pharmacological studies with 2',3',5'-triacetyl-6-azauridine". Cancer Research. 23: 444–453. PMID 14023746.
  4. ↑ Morrey JD, Smee DF, Sidwell RW, Tseng C (July 2002). "Identification of active antiviral compounds against a New York isolate of West Nile virus". Antiviral Research. 55 (1): 107–116. doi:10.1016/s0166-3542(02)00013-x. PMID 12076755.
  5. 1 2 3 Shupack JL, Grieco AJ, Epstein AM, Sansaricq C, Snyderman SE (September 1977). "Azaribine, homocystinemia, and thrombosis". Archives of Dermatology. 113 (9): 1301–1302. doi:10.1001/archderm.1977.01640090149047. PMID 578401.
  6. ↑ Crutcher WA, Moschella SL (February 1975). "Double-blind controlled crossover high-dose study of Azaribine in psoriasis". The British Journal of Dermatology. 92 (2): 199–205. doi:10.1111/j.1365-2133.1975.tb03059.x. PMID 1096923.
  7. ↑ McDonald CJ (1981). "The uses of systemic chemotherapeutic agents in psoriasis". Pharmacology & Therapeutics. 14 (1): 1–24. doi:10.1016/0163-7258(81)90008-5. PMID 7033998.
  8. ↑ "Federal Register, Volume 63 Issue 195 (Thursday, October 8, 1998)". GovInfo. 1998-10-08. Retrieved 2026-03-25.
  9. ↑ Gitel SN, Grieco AJ, Wessler S, Snyderman SE (1979). "The thrombogenicity of 6-azouridine". Haemostasis. 8 (1): 54–57. doi:10.1159/000214291. PMID 456945.
  10. ↑ Slavik M, Smith KJ, Blanc O (December 1982). "Decrease of serum pyridoxal phosphate levels and homocystinemia after administration of 6-azauridine triacetate and their prevention by administration of pyridoxine". Biochemical Pharmacology. 31 (24): 4089–4092. doi:10.1016/0006-2952(82)90664-5. PMID 6186258.
  11. ↑ Drell W, Welch AD (1989). "Azaribine-homocystinemia-thrombosis in historical perspective". Pharmacology & Therapeutics. 41 (1–2): 195–206. doi:10.1016/0163-7258(89)90106-X. PMID 2469090.
  12. ↑ Park JG, Ávila-Pérez G, Nogales A, Blanco-Lobo P, de la Torre JC, Martínez-Sobrido L (January 2020). "Identification and characterization of novel compounds with broad spectrum antiviral activity against influenza A and B viruses". Journal of Virology. 94 (7). doi:10.1128/JVI.02149-19. PMC 7081893. PMID 31941776.