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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H15O3PS2
Molecular Weight 278.328
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENTHION

SMILES

COP(=S)(OC)OC1=CC=C(SC)C(C)=C1

InChI

InChIKey=PNVJTZOFSHSLTO-UHFFFAOYSA-N
InChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3

HIDE SMILES / InChI
Fenthion (trade names include Baytex™, Baycid™, and Tiguvon™, used on livestock) was first registered domestically in 1965 by the Mobay Corp., a U.S. subsidiary of Bayer AG of West Germany. Fenthion is a contact and stomach insecticide used against many sucking, biting pests, especially fruit flies, stem borers, mosquitoes, and Eurygaster cereal bugs. In mosquitoes, it is toxic to both the adult and immature forms (larvae). Once used extensively in the U.S. for controlling intestinal worms, fenthion no longer has FDA approval due to an excess number of poisoning deaths. Like most other organophosphates, its mode of action is via cholinesterase inhibition. It was used mostly for the control of grubs and lice in beef and nonlactating cattle.

Approval Year

PubMed

PubMed

TitleDatePubMed
In vitro and in vivo induction of heat shock (stress) protein (Hsp) gene expression by selected pesticides.
1996 Aug 1
Foetal and adult human CYP3A isoforms in the bioactivation of organophosphorothionate insecticides.
2006 Dec 15
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
Fenthion and terbufos induce DNA damage, the expression of tumor-related genes, and apoptosis in HEPG2 cells.
2011 Aug
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011 Mar 28
Reactivation of plasma butyrylcholinesterase by pralidoxime chloride in patients poisoned by WHO class II toxicity organophosphorus insecticides.
2013 Dec
Piperonyl butoxide increases oxidative toxicity of fenthion in the brain of Oreochromis niloticus.
2014 Feb
Patents

Sample Use Guides

Beef cattle and nonlactating dairy cattle --(i) Amount. It is used at the rate of one-half fluid ounce per 100 pounds of body weight applied topically on the backline of the animal. Only one application per season should be made for grub control and this will also provide initial control of lice. A second application for lice control may be made if animals become reinfested, but no sooner than 35 days after the first treatment. The drug is a solution containing either 5.6 or 13.8 percent fenthion.
Route of Administration: Topical
In Vitro Use Guide
At 50 nM concentrations of fenthion the expression of Hsp89alpha increased by approximately 4.1-fold, while the expression of Hsp89beta increased approximately 5.3-fold, as compared to control value. The expression of Hsp89alpha increased 5.2-fold following incubation of cultured PC-12 cells with 100 nM concentration of fenthion, while at the same concentration the expression of Hsp89beta increased 6.8-fold as compared to control value. At 200 nM concentration of fenthion the expression of Hsp89alpha increased by approximately 5.8-fold and of Hsp89beta increased by approximately 5.6-fold as compared to the control value.
Name Type Language
FENTHION
GREEN BOOK   HSDB   ISO   MART.   MI  
Common Name English
FENTHION [HSDB]
Common Name English
FENTHION [MI]
Common Name English
NSC-755881
Code English
O,O-DIMETHYL O-4-METHYLTHIO-M-TOLYL PHOSPHOROTHIOATE
Common Name English
FENTHION [ISO]
Common Name English
SPOTTON
Brand Name English
TIGUVON
Brand Name English
O,O-DIMETHYL O-(3-METHYL-4-(METHYLTHIO)PHENYL) PHOSPHOROTHIOATE
Systematic Name English
FENTHION [MART.]
Common Name English
FENTHION [GREEN BOOK]
Common Name English
PRO-SPOT
Brand Name English
Classification Tree Code System Code
WHO-VATC QP53AF07
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WHO-VATC QP53BB02
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CFR 21 CFR 524.920
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NCI_THESAURUS C737
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EPA PESTICIDE CODE 53301
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Code System Code Type Description
HSDB
1403
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CHEBI
34761
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DRUG BANK
DB11412
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ALANWOOD
fenthion
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NCI_THESAURUS
C76873
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MESH
D005284
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MERCK INDEX
m5299
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PRIMARY Merck Index
SMS_ID
300000029423
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ChEMBL
CHEMBL1604375
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NSC
755881
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EPA CompTox
DTXSID8020620
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FDA UNII
BL0L45OVKT
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ECHA (EC/EINECS)
200-231-9
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PUBCHEM
3346
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CAS
55-38-9
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WIKIPEDIA
Fenthion
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