WIN54954 | CAS# 107355-45-3 | antipicornavirus

WIN54954
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 414253

CAS#: 107355-45-3

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.

Chemical Structure

WIN54954

CAS# 107355-45-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 414253
Name: WIN54954
CAS#: 107355-45-3
Chemical Formula: C18H20Cl2N2O3
Exact Mass: 382.09
Molecular Weight: 383.270
Elemental Analysis: C, 56.41; H, 5.26; Cl, 18.50; N, 7.31; O, 12.52

Price and Availability

Size	Price	Availability
5mg	USD 150	Ready to ship
10mg	USD 250	Ready to ship
25mg	USD 450	Ready to ship
50mg	USD 750	Ready to ship
100mg	USD 1350	Ready to ship
200mg	USD 2150	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#S21S11C22

QC Data:

View QC data: current batch, Lot#S21S11C22

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	260.91

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.

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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.

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