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Azaribine

Last updated
Azaribine
Azaribine.svg
Clinical data
Trade names Triazure
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  • US:Withdrawn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 InfoCard 100.016.832 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H17N3O9
Molar mass 371.302 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Azaribine received FDA approval in 1975 for the treatment of severe psoriasis, [2] [6] [7] but was subsequently withdrawn from the market in 1976 (with its New Drug Application formally revoked in 1977 [8] ), following reports of life-threatening thromboembolic events.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, 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

  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. ISSN   0031-5982. 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: 444–53. 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): 107–16. 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): 1301–2. doi:10.1001/archderm.1977.01640090149047. PMID   578401.
  6. ↑ 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 . Retrieved 2026-03-25.
  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, 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 . Retrieved 2026-04-01.
  10. ↑ 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 . Retrieved 2026-04-01.
  11. ↑ 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 . Retrieved 2026-04-01.
  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.
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