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
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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3880 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8792849 |
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Target ID: CHEMBL4303 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8792849 |
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Target ID: CHEMBL2094266 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9096284 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Fenthion Approved UseEctoparasiticide |
PubMed
Title | Date | PubMed |
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In vitro and in vivo induction of heat shock (stress) protein (Hsp) gene expression by selected pesticides. | 1996 Aug 1 |
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Foetal and adult human CYP3A isoforms in the bioactivation of organophosphorothionate insecticides. | 2006 Dec 15 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
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Fenthion and terbufos induce DNA damage, the expression of tumor-related genes, and apoptosis in HEPG2 cells. | 2011 Aug |
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Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets. | 2011 Mar 28 |
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Reactivation of plasma butyrylcholinesterase by pralidoxime chloride in patients poisoned by WHO class II toxicity organophosphorus insecticides. | 2013 Dec |
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Piperonyl butoxide increases oxidative toxicity of fenthion in the brain of Oreochromis niloticus. | 2014 Feb |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8792849
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.
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Classification Tree | Code System | Code | ||
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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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34761
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DB11412
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fenthion
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C76873
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D005284
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m5299
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300000029423
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CHEMBL1604375
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755881
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DTXSID8020620
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BL0L45OVKT
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200-231-9
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3346
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55-38-9
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Fenthion
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ACTIVE MOIETY