Chemistry:Azaribine

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

Azaribine was approved in 1975 for clinical use in the treatment of psoriasis,[5][6] but was subsequently withdrawn in 1977 after it was linked to life-threatening thromboembolic events, including both arterial and venous blood clots.[4][7] This side effect is primarily due to the it acting as a vitamin B6 antagonist, which induces a severe functional deficiency of pyridoxal phosphate and the resultant hyperhomocysteinemia.[4][8][9][10] However, it continues to be researched as a potential agent for the treatment of emerging viral diseases.[11]

References

  1. ↑ "New indications for 6-azauridine treatment in man. A review". European Journal of Clinical Pharmacology 4 (2): 77–81. March 1972. doi:10.1007/bf00562501. PMID 4570456. 
  2. ↑ "Clinical and pharmacological studies with 2',3',5'-triacetyl-6-azauridine". Cancer Research 23: 444–53. March 1963. PMID 14023746. 
  3. ↑ "Identification of active antiviral compounds against a New York isolate of West Nile virus". Antiviral Research 55 (1): 107–16. July 2002. doi:10.1016/s0166-3542(02)00013-x. PMID 12076755. 
  4. ↑ 4.0 4.1 4.2 "Azaribine, homocystinemia, and thrombosis". Archives of Dermatology 113 (9): 1301–2. September 1977. doi:10.1001/archderm.1977.01640090149047. PMID 578401. 
  5. ↑ Crutcher, William A.; Moschella, Samuel L. (1975). "Double-blind controlled crossover high-dose study of Azaribine in psoriasis*". British Journal of Dermatology 92 (2): 199–205. doi:10.1111/j.1365-2133.1975.tb03059.x. ISSN 0007-0963. https://academic.oup.com/bjd/article/92/2/199/6663515. Retrieved 2026-03-25. 
  6. ↑ "The uses of systemic chemotherapeutic agents in psoriasis". Pharmacology & Therapeutics 14 (1): 1–24. 1981. doi:10.1016/0163-7258(81)90008-5. PMID 7033998. 
  7. ↑ "Federal Register, Volume 63 Issue 195 (Thursday, October 8, 1998)". 1998-10-08. https://www.govinfo.gov/content/pkg/FR-1998-10-08/html/98-26923.htm. 
  8. ↑ Gitel, Sanford N.; Grieco, Anthony J.; Wessler, Stanford; Snyderman, Selma E. (1979). "The Thrombogenicity of 6-Azauridine". Pathophysiology of Haemostasis and Thrombosis 8 (1): 54–57. doi:10.1159/000214291. ISSN 1424-8832. https://karger.com/article/doi/10.1159/000214291. Retrieved 2026-04-01. 
  9. ↑ Slavik, Milan; Smith, Kenneth J.; Blanc, Oscar (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. https://linkinghub.elsevier.com/retrieve/pii/0006295282906645. Retrieved 2026-04-01. 
  10. ↑ Drell, William; Welch, Arnold D. (1989). "Azarbine-homocystinemia-thrombosis in historical perspective". Pharmacology & Therapeutics 41 (1-2): 195–206. doi:10.1016/0163-7258(89)90106-X. https://linkinghub.elsevier.com/retrieve/pii/016372588990106X. Retrieved 2026-04-01. 
  11. ↑ "Identification and characterization of novel compounds with broad spectrum antiviral activity against influenza A and B viruses". Journal of Virology 94 (7). January 2020. doi:10.1128/JVI.02149-19. PMID 31941776. 



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