Azaribine

Azaribine
Clinical data
Trade names	Azaribine
Legal status
Legal status	US: Withdrawn drug ;
Identifiers
	IUPAC name [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(3,5-dioxo-1,2,4-triazin-2-yl)oxolan-2-yl]methyl acetate;
CAS Number	2169-64-4;
PubChem CID	16574;
ChemSpider	15714;
UNII	K1U80DO9EB;
KEGG	D03029;
ChEBI	CHEBI:88272;
ChEMBL	ChEMBL515914;
CompTox Dashboard (EPA)	DTXSID1022635 ;
ECHA InfoCard	100.016.832
Chemical and physical data
Formula	C14H17N3O9
Molar mass	371.3 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 which was developed 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. Azaribine was approved for clinical use in treatment of psoriasis,[4] but subsequently withdrawn because of toxicity issues,[5][6] however it continues to be researched as a potential agent for the treatment of emerging viral diseases.[7]

References

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.
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.
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.
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.
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.
Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (January 2001). "Evaluation of the characteristics of safety withdrawal of prescription drugs from worldwide pharmaceutical markets-1960 to 1999". Drug Information Journal. 35 (1): 293–317. doi:10.1177/009286150103500134. S2CID 73036562.
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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[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] 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.

[3] 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.

[4] 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.

[5] 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] Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (January 2001). "Evaluation of the characteristics of safety withdrawal of prescription drugs from worldwide pharmaceutical markets-1960 to 1999". Drug Information Journal. 35 (1): 293–317. doi:10.1177/009286150103500134. S2CID 73036562.

[7] 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.