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Details

Stereochemistry ACHIRAL
Molecular Formula C21H22ClN3O2
Molecular Weight 383.871
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLFENPYRAD

SMILES

CCC1=NN(C)C(C(=O)NCC2=CC=C(OC3=CC=C(C)C=C3)C=C2)=C1Cl

InChI

InChIKey=WPALTCMYPARVNV-UHFFFAOYSA-N
InChI=1S/C21H22ClN3O2/c1-4-18-19(22)20(25(3)24-18)21(26)23-13-15-7-11-17(12-8-15)27-16-9-5-14(2)6-10-16/h5-12H,4,13H2,1-3H3,(H,23,26)

HIDE SMILES / InChI

Molecular Formula C21H22ClN3O2
Molecular Weight 383.871
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.fsc.go.jp/english/evaluationreports/pesticide/evaluationreport_tolfenpyrad.pdf

Tolfenpyrad is a pyrazole insecticide, and was discovered by Mitsubishi Chemical Corporation in 1991. The compound acts mainly through the inhibition of the mitochondrial electron transport system. Tolfenpyrad has shown activity against parasitic larval stages (xL3 and L4) of H. contortus in vitro; IC50 values were comparable with those of two commercially available anthelmintics, monepantel and moxidectin. As a pesticide, tolfenpyrad has relatively broad activity against egg, larval, nymphal and adult stages of various arthropods (including Hemiptera, Coleoptera, Diptera, Lepidoptera, Thysanoptera and Acarina), and has been applied to various infested crops. This chemical was developed in Japan and was first approved in 2002; it has been registered for commercial use in several countries other than Japan, including the Dominican Republic, Thailand, the United Arab Emirates, Indonesia and the USA.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.02 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Acute tebufenpyrad and tolfenpyrad poisoning in humans].
2010 Dec
Patents

Sample Use Guides

Beagle dogs (groups of 4 males and 4 females) were given tolfenpyrad, technical grade at 0, 1, 5, or 10 mg/kg bw/day for 1 year by gavage. Dogs in the 10 mg/kg bw/day group were given 20 mg/kg bw/day for the first 5 weeks.
Route of Administration: Oral
The cytotoxicity data show that the viability of SH-SY5Y cells at 24 h was significantly below 80% for concentrations of tebufenpyrad ≥ 3 uM, genotoxicity was observed from 0.01 uM
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:01:52 GMT 2023
Edited
by admin
on Fri Dec 15 19:01:52 GMT 2023
Record UNII
OHA74571QT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOLFENPYRAD
ISO  
Common Name English
4-CHLORO-3-ETHYL-1-METHYL-N-((4-(4-METHYLPHENOXY)PHENYL)METHYL)-1H-PYRAZOLE-5-CARBOXAMIDE
Systematic Name English
TOLFENPYRAD [ISO]
Common Name English
4-CHLORO-3-ETHYL-1-METHYL-N-(4-(P-TOLYLOXY)BENZYL)PYRAZOLE-5-CARBOXAMIDE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 90111
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
Code System Code Type Description
ALANWOOD
tolfenpyrad
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
PRIMARY
CHEBI
38628
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
PRIMARY
PUBCHEM
10110536
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID6057952
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
PRIMARY
CAS
129558-76-5
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
PRIMARY
FDA UNII
OHA74571QT
Created by admin on Fri Dec 15 19:01:52 GMT 2023 , Edited by admin on Fri Dec 15 19:01:52 GMT 2023
PRIMARY