Structure

WIN54954

CAS
107355-45-3
Catalog Number
ACM107355453
Category
Others
Molecular Weight
383.27
Molecular Formula
C18H20Cl2N2O3

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Specification

Description
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.
Synonyms
WIN54954; WIN-54954; WIN 54954
IUPAC Name
Isoxazole, 5-(5-(2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy)pentyl)-3-methyl-
Canonical SMILES
CC1=NOC(CCCCCOC2=C(Cl)C=C(C3=NCCO3)C=C2Cl)=C1
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
InChI Key
JJDHAOLOHQTGMG-UHFFFAOYSA-N
Solubility
To be determined
Appearance
Solid powder
Shelf Life
>2 years if stored properly
Storage
Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
Biological Target
WIN 54954 is a broad-spectrum antipicornavirus agent that has effectiveness against human rhinovirus, echovirus 9 and enterovirus infections.
Drug Formulation
To be determined
Elemental Analysis
C, 56.41; H, 5.26; Cl, 18.50; N, 7.31; O, 12.52
Exact Mass
382.0851
HS Tariff Code
2934.99.9001
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/
Shipping
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.
Stock Solution Storage
0-4 °C for short term (days to weeks), or -20 °C for long term (months).
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