DISOXARIL

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22351989 | https://www.ncbi.nlm.nih.gov/pubmed/14516919 | Driscoll, J.S. (2002) Antiviral Drugs, page 81, retrieved from: https://books.google.ru/books?id=rQ1tAAAAMAAJ

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	2999407
Oral efficacy of WIN 51711 in mice infected with human poliovirus.	1986 Jan	3729333
Prevention of rhinovirus and poliovirus uncoating by WIN 51711, a new antiviral drug.	1986 Jul	3019232
The site of attachment in human rhinovirus 14 for antiviral agents that inhibit uncoating.	1986 Sep 19	3018924
Structure-activity studies of 5-[[4-(4,5-dihydro-2-oxazolyl) phenoxy]alkyl]-3-methylisoxazoles: inhibitors of picornavirus uncoating.	1987 Feb	3027340
Enantiomeric effects of homologues of disoxaril on the inhibitory activity against human rhinovirus-14.	1988 Mar	2831362
Comparative studies on the antirhinovirus activity and the mode of action of the rhinovirus capsid binding agents, chalcone amides.	1990 Feb	2160796
A model for compounds active against human rhinovirus-14 based on X-ray crystallography data.	1990 May	2158559
A comparative test of fifteen compounds against all known human rhinovirus serotypes as a basis for a more rational screening program.	1991 Oct	1666824
Human rhinovirus 14 complexed with fragments of active antiviral compounds.	1994 Jul	8009848
[[[(Thienylcarbonyl)alkyl]oxy]phenyl]- and [[[(pyrrylcarbonyl)alkyl]oxy]phenyl]oxazoline derivatives with potent and selective antihuman rhinovirus activity.	1995 Mar 3	7877145
Development of resistance to disoxaril in Coxsackie B1 virus-infected newborn mice.	2003 Sep	14516919
Synergistic drug combinations against the in vitro replication of Coxsackie B1 virus.	2004 Apr	15026197
Trans-dominant inhibition of RNA viral replication can slow growth of drug-resistant viruses.	2005 Jul	15965477
Physico-chemical characterization of disoxaril-dimethyl-beta-cyclodextrin inclusion complex and in vitro permeation studies.	2006 Feb	16387393
A scalable machine-learning approach to recognize chemical names within large text databases.	2006 Sep 6	17118146
Imaging poliovirus entry in live cells.	2007 Jul	17622193

Sample Use Guides

In Vivo Use Guide

Daily dose 25mg/kg for 10 days

Route of Administration: Other

Name

Type

Language

DISOXARIL

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