U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DISOXARIL

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

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
[[(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
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
A scalable machine-learning approach to recognize chemical names within large text databases.
2006 Sep 6

Sample Use Guides

Daily dose 25mg/kg for 10 days
Route of Administration: Other
Name Type Language
DISOXARIL
INN   USAN  
INN   USAN  
Official Name English
WIN 51,711
Code English
3-METHYL-5-(7-(P-2-OXAZOLIN-2-YLPHENOXY)HEPTYL)ISOXAZOLE
Common Name English
disoxaril [INN]
Common Name English
ISOXAZOLE, 5-(7-(4-(4,5-DIHYDRO-2-OXAZOLYL)PHENOXY)HEPTYL)-3-METHYL-
Systematic Name English
DISOXARIL [USAN]
Common Name English
WIN-51711
Code English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Sat Dec 16 16:17:41 GMT 2023 , Edited by admin on Sat Dec 16 16:17:41 GMT 2023
Code System Code Type Description
SMS_ID
100000081097
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PRIMARY
MESH
C045978
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PUBCHEM
55717
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ChEMBL
CHEMBL283639
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CAS
87495-31-6
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INN
5919
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EPA CompTox
DTXSID70236354
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USAN
W-27
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FDA UNII
FX8Q9PI4VP
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EVMPD
SUB06322MIG
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NCI_THESAURUS
C81607
Created by admin on Sat Dec 16 16:17:41 GMT 2023 , Edited by admin on Sat Dec 16 16:17:41 GMT 2023
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