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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
297.6 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Azoxystrobin inhibited Botrytis cinerea fungi in vitro with EC50 value of 0.0884 uM.
Substance Class Chemical
Record UNII
NYH7Y08IPM
Record Status Validated (UNII)
Record Version