WIN54954

• CAT Number: I038296
• CAS Number: 107355-45-3
• Molecular Formula: C18H20Cl2N2O3
• Molecular Weight: 383.27
• Purity: 98%
• Synonyms: WIN54954; WIN-54954; WIN 54954
• Target: Enterovirus
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Isoxazole, 5-(5-(2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy)pentyl)-3-methyl-
• InChI: InChI=1S/C18H20Cl2N2O3/c1-12-9-14(25-22-12)5-3-2-4-7-23-17-15(19)10-13(11-16(17)20)18-21-6-8-24-18/h9-11H,2-8H2,1H3
• InChIKey: JJDHAOLOHQTGMG-UHFFFAOYSA-N
• SMILES: CC1=NOC(CCCCCOC2=C(Cl)C=C(C3=NCCO3)C=C2Cl)=C1

WIN54954 is a broad-spectrum antipicornavirus drug. WIN 54 954 is a potent antiviral agent with a highly significant effect on survival in CBV-induced myocarditis in the A/J mouse if treatment is started early. WIN 54954 effectively reduces virus replication and islet histologic changes acutely and decreases, at 7 weeks, both the metabolic alteration associated with diabetes mellitus and the incidence of detectable viral RNA in the pancreas.

Reference

1: See DM, Tilles JG. WIN 54954 treatment of mice infected with a diabetogenic strain of group B coxsackievirus. Antimicrob Agents Chemother. 1993 Aug;37(8):1593-8. doi: 10.1128/AAC.37.8.1593. PMID: 8215268; PMCID: PMC188025.
2: Heim A, Pfetzing U, Müller G, Grumbach IM. Antiviral activity of WIN 54954 in coxsackievirus B2 carrier state infected human myocardial fibroblasts. Antiviral Res. 1998 Jan;37(1):47-56. doi: 10.1016/s0166-3542(97)00056-9. PMID: 9497072.
3: Woods MG, Diana GD, Rogge MC, Otto MJ, Dutko FJ, McKinlay MA. In vitro and in vivo activities of WIN 54954, a new broad-spectrum antipicornavirus drug. Antimicrob Agents Chemother. 1989 Dec;33(12):2069-74. doi: 10.1128/AAC.33.12.2069. PMID: 2559655; PMCID: PMC172823.
4: Ilbäck NG, Wesslén L, Pauksen K, Stålhandske T, Friman G, Fohlman J. Effects of the antiviral WIN 54954 and the immune modulator LS 2616 on cachectin/TNF and gamma-interferon responses during viral heart disease. Scand J Infect Dis Suppl. 1993;88:117-23. PMID: 8390714.
5: See DM, Tilles JG. Treatment of Coxsackievirus A9 myocarditis in mice with WIN 54954. Antimicrob Agents Chemother. 1992 Feb;36(2):425-8. doi: 10.1128/AAC.36.2.425. PMID: 1318683; PMCID: PMC188451.
6: Turner RB, Dutko FJ, Goldstein NH, Lockwood G, Hayden FG. Efficacy of oral WIN 54954 for prophylaxis of experimental rhinovirus infection. Antimicrob Agents Chemother. 1993 Feb;37(2):297-300. doi: 10.1128/AAC.37.2.297. PMID: 8383943; PMCID: PMC187656.
7: Kytö V, Saraste A, Fohlman J, Ilbäck NG, Harvala H, Vuorinen T, Hyypiä T. Cardiomyocyte apoptosis after antiviral WIN 54954 treatment in murine coxsackievirus B3 myocarditis. Scand Cardiovasc J. 2002 May;36(3):187-92. doi: 10.1080/cdv.36.3.187.192. PMID: 12079640.
8: Pauksen K, Ilbäck NG, Friman G, Fohlman J. Therapy of coxsackie virus B3-induced myocarditis with WIN 54954 in different formulations. Scand J Infect Dis Suppl. 1993;88:125-30. PMID: 8390715.
9: Egan JA, Nugent RP, Filer CN. Potent antiviral agent WIN 54954: high specific activity labelling with tritium. Appl Radiat Isot. 2004 Jun;60(6):851-3. doi: 10.1016/j.apradiso.2004.03.002. PMID: 15110350; PMCID: PMC7127203.
10: Charman SA, Charman WN, Rogge MC, Wilson TD, Dutko FJ, Pouton CW. Self- emulsifying drug delivery systems: formulation and biopharmaceutic evaluation of an investigational lipophilic compound. Pharm Res. 1992 Jan;9(1):87-93. doi: 10.1023/a:1018987928936. PMID: 1589415.