WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H319911
CAS#: 87495-31-6
Description: Disoxaril, also known as BRN 3626820 and WIN 51711, is an antipicornavirus agent. Disoxaril inhibits enterovirus replication by binding to the hydrophobic pocket within the VP1 coat protein, thus stabilizing the virion and blocking its uncoating. When combined with enviroxime and disoxaril, two selective picornavirus inhibitors exert a marked synergistic inhibitory effect on poliovirus type 1 replication in FL cells.
Hodoodo Cat#: H319911
Name: Disoxaril
CAS#: 87495-31-6
Chemical Formula: C20H26N2O3
Exact Mass: 342.19
Molecular Weight: 342.439
Elemental Analysis: C, 70.15; H, 7.65; N, 8.18; O, 14.02
This product is not in stock, which may be available by custom synthesis.
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Synonym: WIN-51711; WIN51711; WIN 51711; WIN-51,711; WIN51,711; WIN 51,711;BRN-3626820; BRN 3626820; BRN3626820; Disoxaril
IUPAC/Chemical Name: 5-(7-(4-(4,5-dihydrooxazol-2-yl)phenoxy)heptyl)-3-methylisoxazole
InChi Key: FKLJPTJMIBLJAV-UHFFFAOYSA-N
InChi Code: InChI=1S/C20H26N2O3/c1-16-15-19(25-22-16)7-5-3-2-4-6-13-23-18-10-8-17(9-11-18)20-21-12-14-24-20/h8-11,15H,2-7,12-14H2,1H3
SMILES Code: CC1=NOC(CCCCCCCOC2=CC=C(C3=NCCO3)C=C2)=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: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 342.44 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Nikolova I, Galabov AS, Petkova R, Chakarov S, Atanasov B. Disoxaril mutants of Coxsackievirus B1: phenotypic characteristics and analysis of the target VP1 gene. Z Naturforsch C. 2011 Nov-Dec;66(11-12):627-36. PubMed PMID: 22351989.
2: Ventura CA, Giannone I, Musumeci T, Pignatello R, Ragni L, Landolfi C, Milanese C, Paolino D, Puglisi G. Physico-chemical characterization of disoxaril-dimethyl-beta-cyclodextrin inclusion complex and in vitro permeation studies. Eur J Med Chem. 2006 Feb;41(2):233-40. Epub 2006 Jan 4. PubMed PMID: 16387393.
3: Nikolova I, Galabov AS. Development of resistance to disoxaril in Coxsackie B1 virus-infected newborn mice. Antiviral Res. 2003 Sep;60(1):35-40. PubMed PMID: 14516919.
4: Nikolaeva L, Galabov AS. Antiviral effect of the combination of enviroxime and disoxaril on coxsackievirus B1 infection. Acta Virol. 2000 Apr;44(2):73-8. PubMed PMID: 10989697.
5: Mazzei M, Dondero R, Ledda B, Demontis F, Vargiu L. Disoxaril-related 3-(diethylamino)-5-phenylisoxazoles. Farmaco. 2000 Feb;55(2):119-24. PubMed PMID: 10782382.
6: Nikolaeva L, Galabov AS. Cytotoxicity of the synergistic antienteroviral combination of enviroxime and disoxaril. Acta Virol. 1999 Aug;43(4):263-5. PubMed PMID: 10749374.
7: Nikolaeva L, Galabov AS. Synergistic inhibitory effect of enviroxime and disoxaril on poliovirus type 1 replication. Acta Virol. 1995 Dec;39(5-6):235-41. PubMed PMID: 8722291.
8: Diana GD, Volkots DL, Nitz TJ, Bailey TR, Long MA, Vescio N, Aldous S, Pevear DC, Dutko FJ. Oxadiazoles as ester bioisosteric replacements in compounds related to disoxaril. Antirhinovirus activity. J Med Chem. 1994 Jul 22;37(15):2421-36. PubMed PMID: 8057290.
9: Frisk G, Halloran M, Didarholm H. Stabilization of the antigenicity of coxsackie B procapsids by disoxaril. J Virol Methods. 1993 Dec 15;45(2):235-9. PubMed PMID: 8113348.
10: Diana GD, Cutcliffe D, Volkots DL, Mallamo JP, Bailey TR, Vescio N, Oglesby RC, Nitz TJ, Wetzel J, Giranda V, et al. Antipicornavirus activity of tetrazole analogues related to disoxaril. J Med Chem. 1993 Oct 29;36(22):3240-50. PubMed PMID: 8230114.
11: Mallamo JP, Diana GD, Pevear DC, Dutko FJ, Chapman MS, Kim KH, Minor I, Oliveira M, Rossmann MG. Conformationally restricted analogues of disoxaril: a comparison of the activity against human rhinovirus types 14 and 1A. J Med Chem. 1992 Dec 11;35(25):4690-5. PubMed PMID: 1335081.
12: Rombaut B, Boeyé A. In vitro assembly of poliovirus 14 S subunits: disoxaril stabilization as a model for the antigenicity conferring activity of infected cell extracts. Virology. 1991 Feb;180(2):788-92. PubMed PMID: 1703372.
13: Rombaut B, Brioen P, Boeyé A. Disoxaril stabilization and immunogenicity of poliovirus procapsids. J Gen Virol. 1990 May;71 ( Pt 5):1081-6. PubMed PMID: 2161045.
14: Jubelt B, Wilson AK, Ropka SL, Guidinger PL, McKinlay MA. Clearance of a persistent human enterovirus infection of the mouse central nervous system by the antiviral agent disoxaril. J Infect Dis. 1989 May;159(5):866-71. PubMed PMID: 2540248.
15: Diana GD, Otto MJ, Treasurywala AM, McKinlay MA, Oglesby RC, Maliski EG, Rossmann MG, Smith TJ. Enantiomeric effects of homologues of disoxaril on the inhibitory activity against human rhinovirus-14. J Med Chem. 1988 Mar;31(3):540-4. PubMed PMID: 2831362.
16: Zeichhardt H, Otto MJ, McKinlay MA, Willingmann P, Habermehl KO. Inhibition of poliovirus uncoating by disoxaril (WIN 51711). Virology. 1987 Sep;160(1):281-5. PubMed PMID: 2820136.
