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
| Molecular Formula | C10H15O3PS2 |
| Molecular Weight | 278.328 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
| Title | Date | PubMed |
|---|---|---|
| Differences in the mode of lethality produced through intravenous and oral administration of organophosphorus insecticides in rats. | 1991 Apr |
|
| In vitro and in vivo induction of heat shock (stress) protein (Hsp) gene expression by selected pesticides. | 1996 Aug 1 |
|
| Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. | 2004 Apr |
|
| Evaluation of xenobiotic N- and S-oxidation by variant flavin-containing monooxygenase 1 (FMO1) enzymes. | 2004 Apr |
|
| 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 |
|
| Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program. | 2010 Mar 15 |
|
| 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 |
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
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
Created
by
admin
on
Edited
Fri Dec 15 15:08:38 UTC 2023
by
admin
on
Fri Dec 15 15:08:38 UTC 2023
|
| Record UNII |
BL0L45OVKT
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
WHO-VATC |
QP53AF07
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
||
|
WHO-VATC |
QP53BB02
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
||
|
CFR |
21 CFR 524.920
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
||
|
NCI_THESAURUS |
C737
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
||
|
EPA PESTICIDE CODE |
53301
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
1403
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | |||
|
34761
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
DB11412
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
fenthion
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
C76873
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | |||
|
D005284
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | |||
|
m5299
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | Merck Index | ||
|
300000029423
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | |||
|
CHEMBL1604375
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
755881
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | |||
|
DTXSID8020620
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
BL0L45OVKT
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
200-231-9
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
3346
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY | |||
|
55-38-9
Created by
admin on Fri Dec 15 15:08:38 UTC 2023 , Edited by admin on Fri Dec 15 15:08:38 UTC 2023
|
PRIMARY | |||
|
Fenthion
Created by
admin on Fri Dec 15 15:08:39 UTC 2023 , Edited by admin on Fri Dec 15 15:08:39 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
