Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H26N2O3 |
| Molecular Weight | 342.432 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NOC(CCCCCCCOC2=CC=C(C=C2)C3=NCCO3)=C1
InChI
InChIKey=FKLJPTJMIBLJAV-UHFFFAOYSA-N
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
| Molecular Formula | C20H26N2O3 |
| Molecular Weight | 342.432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Disoxaril is the antipicornavirus drug. It is an isoxazole heterocyclic compound and a member of the antiviral series commonly referred to as WIN compounds. Disoxaril inhibits enterovirus replication by binding to the hydrophobic pocket within the VP1 coat protein, thus stabilizing the virion and blocking its uncoating. The amino acid sequence of a large VP1 196-258 peptide (disoxaril-binding region) of CVB1/RESISTANT was significantly different from that of the CVB1/SOF (sensitive). Crucially important changes in CVB1/RES were two point mutations, M213H and F237L, both in the ligand-binding pocket. Treatment with disoxaril in newborn mice infected with Coxsackie B1 virus, for 10 days post virus inoculation decreased the virus titer in the mouse brain till day 7.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [[(4,5-Dihydro-2-oxazolyl)phenoxy]alkyl]isoxazoles. Inhibitors of picornavirus uncoating. | 1985 Dec |
|
| Oral efficacy of WIN 51711 in mice infected with human poliovirus. | 1986 Jan |
|
| Prevention of rhinovirus and poliovirus uncoating by WIN 51711, a new antiviral drug. | 1986 Jul |
|
| The site of attachment in human rhinovirus 14 for antiviral agents that inhibit uncoating. | 1986 Sep 19 |
|
| Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating. | 1987 Feb |
|
| Enantiomeric effects of homologues of disoxaril on the inhibitory activity against human rhinovirus-14. | 1988 Mar |
|
| Comparative studies on the antirhinovirus activity and the mode of action of the rhinovirus capsid binding agents, chalcone amides. | 1990 Feb |
|
| A model for compounds active against human rhinovirus-14 based on X-ray crystallography data. | 1990 May |
|
| A comparative test of fifteen compounds against all known human rhinovirus serotypes as a basis for a more rational screening program. | 1991 Oct |
|
| Human rhinovirus 14 complexed with fragments of active antiviral compounds. | 1994 Jul |
|
| [[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity. | 1995 Mar 3 |
|
| Development of resistance to disoxaril in Coxsackie B1 virus-infected newborn mice. | 2003 Sep |
|
| Synergistic drug combinations against the in vitro replication of Coxsackie B1 virus. | 2004 Apr |
|
| Trans-dominant inhibition of RNA viral replication can slow growth of drug-resistant viruses. | 2005 Jul |
|
| Physico-chemical characterization of disoxaril-dimethyl-beta-cyclodextrin inclusion complex and in vitro permeation studies. | 2006 Feb |
|
| A scalable machine-learning approach to recognize chemical names within large text databases. | 2006 Sep 6 |
|
| Imaging poliovirus entry in live cells. | 2007 Jul |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:17:41 GMT 2023
by
admin
on
Sat Dec 16 16:17:41 GMT 2023
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| Record UNII |
FX8Q9PI4VP
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C281
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C045978
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55717
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87495-31-6
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C81607
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