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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

Molecular Formula C10H15O3PS2
Molecular Weight 278.328
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Fenthion

PubMed

Sample Use Guides

In Vivo Use Guide
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.
Substance Class Chemical
Record UNII
BL0L45OVKT
Record Status Validated (UNII)
Record Version