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// Workers AI · dad joke modeWhat did Azaribine say to its friend? "You're a ribe-uting companion".

From Wikipedia, the free encyclopedia

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  • US: Withdrawn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,[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]

Azaribine received FDA approval in 1975 for the treatment of severe psoriasis,[2][6][7] but was subsequently withdrawn from the market in 1976 (with its New Drug Application formally revoked in 1977[8]), following reports of life-threatening thromboembolic events.[2][5] These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, are 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

[edit]
  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.