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Details

Stereochemistry ACHIRAL
Molecular Formula C22H17N3O5
Molecular Weight 403.3875
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZOXYSTROBIN

SMILES

CO\C=C(\C(=O)OC)C1=C(OC2=NC=NC(OC3=C(C=CC=C3)C#N)=C2)C=CC=C1

InChI

InChIKey=WFDXOXNFNRHQEC-GHRIWEEISA-N
InChI=1S/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+

HIDE SMILES / InChI

Molecular Formula C22H17N3O5
Molecular Weight 403.3875
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Azoxystrobin is the first of a new class of pesticidal compounds called ß-methoxyacrylates, which are derived from the naturally-occurring strobilurins. Azoxystrobin is a broad spectrum fungicide with activity against several diseases on many edible crops and ornamental plants. Some diseases controlled or prevented are rice blast, rusts, downy mildew, powdery mildew, late blight, apple scab, and Septoria. Azoxystrobin is marketed by Syngenta as single AS products under several trade names, the major ones for crop protection being: Amistar, Abound, Priori, Quadris, Dynasty for seed treatments, and Heritage for turf. Azoxystrobin (AZOX), a Qo inhibitor of mitochondrial respiratory complex III, exerts whole-body beneficial effects on the regulation of glucose and lipid homeostasis in high-fat diet-fed mice. Chronic treatment with AZOX reduced body weight and significantly improved glucose tolerance and insulin sensitivity in high-fat diet-fed mice. AZOX treatment resulted in decreased triacylglycerol accumulation and down-regulated the expression of genes involved in liver lipogenesis. AZOX increased glucose uptake in L6 myotubes and 3T3-L1 adipocytes and inhibited de novo lipogenesis in HepG2 cells.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
297.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Azoxystrobin is non-oncogenic in the rat. Based on a study which administered azoxystrobin in the diets of rats the following values were recorded: male rat 3.6 mg/kg/day, female rat 3.6 mg/kg/day at 60 ppm diet; male rat 18.2 mg/kg/day, female rat 22.3 mg/kg/day at 300 ppm diet; male rat 82.4 mg/kg/day, female rat 117.6 mg/kg/day at 1500/750 ppm diet, respectively. http://pmep.cce.cornell.edu/profiles/extoxnet/24d-captan/azoxystrobin-ext.html
High-fat diet-fed mice were orally administered either vehicle (100% corn oil) or Azoxystrobin (25 mg/kg/day) for 35 days.
Route of Administration: Oral
Azoxystrobin inhibited Botrytis cinerea fungi in vitro with EC50 value of 0.0884 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:35:43 GMT 2023
Edited
by admin
on Fri Dec 15 18:35:43 GMT 2023
Record UNII
NYH7Y08IPM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZOXYSTROBIN
HSDB   ISO   MI  
Common Name English
METHYL (.ALPHA.E)-2-((6-(2-CYANOPHENOXY)-4-PYRIMIDINYL)OXY)-.ALPHA.-(METHOXYMETHYLENE)BENZENEACETATE
Common Name English
(.ALPHA.E)-2-((6-(2-CYANOPHENOXY)-4-PYRIMIDINYL)OXY)-.ALPHA.-(METHOXYMETHYLENE)BENZENEACETIC ACID METHYL ESTER
Common Name English
QUADRIS
Brand Name English
METHYL (2E)-2-(2-(6-(2-CYANOPHENOXY)PYRIMIDIN-4-YLOXY)PHENYL)-3-METHOXYACRYLATE
Systematic Name English
AZOXYSTROBIN [HSDB]
Common Name English
HERITAGE
Brand Name English
ICI-A-5504
Common Name English
AZOXYSTROBIN [ISO]
Common Name English
AZOXYSTROBIN [MI]
Common Name English
AMISTAR
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128810
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
Code System Code Type Description
FDA UNII
NYH7Y08IPM
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID0032520
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
PRIMARY
DRUG BANK
DB07401
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
PRIMARY
CAS
131860-33-8
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
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MESH
C087670
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
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HSDB
7017
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
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PUBCHEM
3034285
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
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ALANWOOD
azoxystrobin
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
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WIKIPEDIA
AZOXYSTROBIN
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
PRIMARY
ECHA (EC/EINECS)
ANNEX I INDEX 607-256-00-X
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
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MERCK INDEX
m2187
Created by admin on Fri Dec 15 18:35:43 GMT 2023 , Edited by admin on Fri Dec 15 18:35:43 GMT 2023
PRIMARY Merck Index