Synonym
WIN54954; WIN-54954; WIN 54954;
IUPAC/Chemical Name
Isoxazole, 5-(5-(2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy)pentyl)-3-methyl-
InChi Key
JJDHAOLOHQTGMG-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CC1=NOC(CCCCCOC2=C(Cl)C=C(C3=NCCO3)C=C2Cl)=C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
WIN 54954 is a broad-spectrum antipicornavirus agent that has effectiveness against human rhinovirus, echovirus 9 and enterovirus infections.
In vitro activity:
WIN 54954 reduced the virus titers of myocardial fibroblast cultures from 3.3×105 PFU/ml (SD 1.4×105) to 2.96×103 PFU/ml (SD 6.0x102) after 4 days of application. The antiproliferative effect of WIN 54954 in myocardial fibroblast cultures was very low (IC50>5 μg/ml) and this confirms the high selectivity of WIN 54954 action. After 16 days of WIN 54954 (0.025–1 μg/ml) application, infectious virus progeny was completely suppressed with the exception of a single culture in the 0.025 μg/ml dose schedule and a single culture in the 0.5 μg/ml dose schedule. A WIN 54954 resistant CVB2 was isolated from the latter culture. The EC90 of this isolate as determined in Vero cell had increased significantly to 0.81 μg/ml compared to 0.197 μg/ml of the stock virus and the EC50 had increased slightly to 0.026 μg/ml compared to 0.018 μg/ml of the stock virus (standard deviations of EC50 and EC <5%).
Reference: Antiviral Res. 1998 Jan;37(1):47-56. https://pubmed.ncbi.nlm.nih.gov/9497072/
In vivo activity:
WIN 54954 reduced the virus titers of myocardial fibroblast cultures from 3.3×105 PFU/ml (SD 1.4×105) to 2.96×103 PFU/ml (SD 6.0x102) after 4 days of application. The antiproliferative effect of WIN 54954 in myocardial fibroblast cultures was very low (IC50>5 μg/ml) and this confirms the high selectivity of WIN 54954 action. After 16 days of WIN 54954 (0.025–1 μg/ml) application, infectious virus progeny was completely suppressed with the exception of a single culture in the 0.025 μg/ml dose schedule and a single culture in the 0.5 μg/ml dose schedule. A WIN 54954 resistant CVB2 was isolated from the latter culture. The EC90 of this isolate as determined in Vero cell had increased significantly to 0.81 μg/ml compared to 0.197 μg/ml of the stock virus and the EC50 had increased slightly to 0.026 μg/ml compared to 0.018 μg/ml of the stock virus (standard deviations of EC50 and EC <5%).
Reference: Antiviral Res. 1998 Jan;37(1):47-56. https://pubmed.ncbi.nlm.nih.gov/9497072/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
260.91 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
383.27
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. 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.
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. 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.
In vitro protocol:
1. 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.
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.
In vivo protocol:
1. 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.
2. 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.
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.
