FENTHION

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 Search

SMILES

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

Description
Sources: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=524.920 | http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenthion-ext.html | https://www.beyondpesticides.org/assets/media/documents/pesticides/factsheets/Fenthion.pdf

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
Heat shock protein HSP 90-alpha 12 Target ID: CHEMBL3880 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8792849	Activator 1447
Heat shock protein HSP 90-beta 14 Target ID: CHEMBL4303 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8792849	Activator 1447
Protein kinase C (PKC) 44 Target ID: CHEMBL2094266 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9096284	Activator 1447
Acetylcholinesterase 209 Target ID: CHEMBL3199 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2147549 \| https://www.ncbi.nlm.nih.gov/pubmed/2773698 \| https://www.ncbi.nlm.nih.gov/pubmed/7991222 \| https://www.ncbi.nlm.nih.gov/pubmed/2385836 \| http://www.inchem.org/documents/jmpr/jmpmono/v071pr06.htm	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Helminthiasis in cattle 3 Sources: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=524.920 http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenthion-ext.html	Preventing		Approved 8583	Fenthion Approved Use Ectoparasiticide

C_max

Value	Dose	Co-administered	Analyte	Population
0.4 OTHER OTHER https://agris.fao.org/agris-search/search.do?recordID=DJ20220318542	10 mg/kg bw single, topical dose: 10 mg/kg bw route of administration: Topical experiment type: SINGLE co-administered:		FENTHION	Bos taurus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
52.5 h OTHER https://agris.fao.org/agris-search/search.do?recordID=DJ20220318542	10 mg/kg bw single, topical dose: 10 mg/kg bw route of administration: Topical experiment type: SINGLE co-administered:		FENTHION	Bos taurus population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 inhibitor 2252 substrate 1946 inducer 1087	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 CYP19A1 429 OATP1B3 961 CYP2C19 2057 CYP1A2 2153	CYP2C19 1119 CYP1A2 1197 FMO3 77 FMO1 25 CYP2C8 810 CYP2B6 776 CYP1A1 389 CYP2A6 626 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 19.0	inconclusive [IC50 27.5404 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 252.0	no
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTYwNDM3NSJ9fQ==	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 316.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 2.0	yes [IC50 0.7098 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 3.0	yes [IC50 1.6196 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTYwNDM3NSJ9fQ==	yes [IC50 12.5893 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 6.0	yes [IC50 3.8902 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE2MDQzNzUifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE2MDQzNzUifX0=	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	likely
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	likely
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	likely
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3346#section=Biological-Test-Results Page: 316 \| 318	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 1.6 uM]
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 12 uM]
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 2.4 uM]
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 2.7 uM]
FMO1 25	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 2.7 uM]
FMO3 77	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 39 uM]
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 8 uM]
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18845175/	yes [Km 89 uM]

PubMed

Title	Date	PubMed
Piperonyl butoxide increases oxidative toxicity of fenthion in the brain of Oreochromis niloticus.	2014-02	24497177
Reactivation of plasma butyrylcholinesterase by pralidoxime chloride in patients poisoned by WHO class II toxicity organophosphorus insecticides.	2013-12	24052565
Fenthion and terbufos induce DNA damage, the expression of tumor-related genes, and apoptosis in HEPG2 cells.	2011-08	21538558
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.	2011-03-28	21251949
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.	2010-03-15	20143881
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Foetal and adult human CYP3A isoforms in the bioactivation of organophosphorothionate insecticides.	2006-12-15	17110060
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells.	2004-04	15064155
Evaluation of xenobiotic N- and S-oxidation by variant flavin-containing monooxygenase 1 (FMO1) enzymes.	2004-04	14976351
In vitro and in vivo induction of heat shock (stress) protein (Hsp) gene expression by selected pesticides.	1996-08-01	8792849
Differences in the mode of lethality produced through intravenous and oral administration of organophosphorus insecticides in rats.	1991-04	1855619

Patents

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.

Name

Type

Language

O,O-DIMETHYL O-(3-METHYL-4-(METHYLTHIO)PHENYL) PHOSPHOROTHIOATE

Preferred Name

English

FENTHION

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

FENTHION [MART.]

Common Name

English

FENTHION [GREEN BOOK]

Common Name

English

PRO-SPOT

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QP53AF07