METHOXYCHLOR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H15Cl3O2
Molecular Weight	345.648
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C(C2=CC=C(OC)C=C2)C(Cl)(Cl)Cl

InChI

InChIKey=IAKOZHOLGAGEJT-UHFFFAOYSA-N

InChI=1S/C16H15Cl3O2/c1-20-13-7-3-11(4-8-13)15(16(17,18)19)12-5-9-14(21-2)10-6-12/h3-10,15H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C16H15Cl3O2
Molecular Weight	345.648
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.epa.gov/sites/production/files/2016-09/documents/methoxychlor.pdf | https://www3.epa.gov/pesticides/chem_search/ppls/000352-00167-19690424.pdf | http://pmep.cce.cornell.edu/profiles/extoxnet/haloxyfop-methylparathion/methoxychlor-ext.html

Methoxychlor is a contact and stomach insecticide effective against a wide range of pests encountered in agriculture, households, and ornamental plantings. It was registered for use on fruits, vegetables, forage crops and on shade trees. Methoxychlor was also registered for veterinary use as a poison to kill parasites on dairy and beef cattle. Exposure to methoxychlor may occur during its manufacture or use as a pesticide. In an acute oral study in animals, changes in the liver were reported. Dermal contact with methoxychlor is slightly irritating to the skin. The use of methoxychlor as a pesticide was banned in the United States in 2003 and in the European Union in 2002.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 8297	15.47 µM [IC50]
Cytochrome P450 2C11 2 Target ID: CHEMBL4971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 8297	22.45 µM [IC50]
Cytochrome P450 2C6 1 Target ID: CHEMBL1907986 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 8297	14.84 µM [IC50]
Cytochrome P450 2B6 19 Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10101147	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lice infestation 5 Sources: https://www3.epa.gov/pesticides/chem_search/ppls/000352-00167-19690424.pdf	Curative		Approved 8429	Marlate Approved Use Applied for the control of certain external parasites.
Flea infestations 12 Sources: https://www3.epa.gov/pesticides/chem_search/ppls/000352-00075-19780918.pdf	Curative		Approved 8429	Marlate Approved Use Applied for the control of certain external parasites.

PubMed

Title	Date	PubMed
Methoxychlor stimulates the mouse lactoferrin gene promoter through a GC-rich element.	2002	11908639
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor.	2002 Apr	11896288
Assessment of interactions of diverse ternary mixtures in an estrogen receptor-alpha reporter assay.	2002 Apr 1	11922773
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis.	2002 Apr 15	11969380
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region.	2002 Aug	12196010
Methoxychlor may cause ovarian follicular atresia and proliferation of the ovarian epithelium in the mouse.	2002 Aug	12151644
Uterine responsiveness to estradiol and DNA methylation are altered by fetal exposure to diethylstilbestrol and methoxychlor in CD-1 mice: effects of low versus high doses.	2002 Aug 15	12217638
Determination of organochlorine pesticides in seawater using liquid-phase hollow fibre membrane microextraction and gas chromatography-mass spectrometry.	2002 Aug 30	12236503
Analysis of pesticides and PCB congeners in serum by GC/MS with SPE sample cleanup.	2002 Aug 5	12191885
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.	2002 Dec	12623674
Determination of estrogenic activity in landfill leachate by simplified yeast two-hybrid assay.	2002 Dec	12509063
An avian bioassay for environmental estrogens: the growth response of zebra finch (Taeniopygia guttata) chick oviduct to oral estrogens.	2002 Dec	12463562
Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents.	2002 Dec	12460799
Induction of oxidative stress in the rat testis after short-term exposure to the organochlorine pesticide methoxychlor.	2002 Dec	12451445
Enantioselective metabolism of the endocrine disruptor pesticide methoxychlor by human cytochromes P450 (P450s): major differences in selective enantiomer formation by various P450 isoforms.	2002 Dec	12433799
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002 Jul	12224631
Workshop report. Children as a special subpopulation: focus on immunotoxicity. Federal Institute for Health Protection of Consumers and Veterinary Medicine (BgVV), 15-16 November 2001, Berlin, Germany.	2002 Jul	12222155
Enhancing effects of beta-estradiol 3-benzoate but not methoxychlor on the promotion/progression stage of chemically-induced mammary carcinogenesis in ovariectomized rats.	2002 Jul	12149140
Is exposure to endocrine disrupting compounds during fetal/post-natal development affecting the reproductive potential of farm animals?	2002 Jul	12142238
Effect of methoxychlor on the antioxidant system in mitochondrial and microsome-rich fractions of rat testis.	2002 Jul 1	12062931
Detection of estrogenic activity in sediment-associated compounds using in vitro reporter gene assays.	2002 Jul 3	12109482
Methoxychlor alters the predator-prey relationship between dragonfly naiads and salamander larvae.	2002 Jun	12012050
Thyroid toxicity due to subchronic exposure to a complex mixture of 16 organochlorines, lead, and cadmium.	2002 Jun	12011480
Organochlorine pesticides directly regulate gonadotropin-releasing hormone gene expression and biosynthesis in the GT1-7 hypothalamic cell line.	2002 Jun 28	12088877
The effect of methoxychlor on the epididymal antioxidant system of adult rats.	2002 Mar-Apr	11955947
Comparative assessment of endocrine modulators with oestrogenic activity. II. Persistent organochlorine pollutants.	2002 May	12029381
PCDDs/PCDFs, PCBs, and organochlorine pesticides in eggs of Eurasian sparrowhawks (Accipiter nisus), hobbies (Falco subbuteo), and northern goshawks (Accipiter gentilis) collected in the area of Berlin-Brandenburg, Germany.	2002 May	11994791
Effects of subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects.	2002 May	11961226
Effects of primary exposure to environmental and natural estrogens on vitellogenin production in carp (Cyprinus carpio) hepatocytes.	2002 May	11961218
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.	2002 Nov	12389925
The pesticide methoxychlor given orally during the perinatal/juvenile period, reduced the spermatogenic potential of males as adults by reducing their Sertoli cell number.	2002 Nov-Dec	12625421
Effect of tolerance to insecticides on substrate penetration by Formosan subterranean termites (Isoptera: Rhinotermitidae).	2002 Oct	12403426
A comparison of the estrogenic potencies of estradiol, ethynylestradiol, diethylstilbestrol, nonylphenol and methoxychlor in vivo and in vitro.	2002 Oct 2	12204590
Thymic atrophy induced by methoxychlor in rat pups.	2002 Oct 5	12270678
Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: pathways involving a novel catechol metabolite.	2002 Sep	12167570
The rat as a model in developmental immunotoxicology.	2002 Sep-Oct	12458909
Environmental estrogens alter early development in Xenopus laevis.	2003 Apr	12676604
The multidrug resistance-associated protein 1 transports methoxychlor and protects the seminiferous epithelium from injury.	2003 Apr 30	12765240
Inhibition of gonadotropin-induced oviposition and ovarian steroidogenesis in the African clawed frog (Xenopus laevis) by the pesticide methoxychlor.	2003 Feb 12	12560167
Expression profiling of estrogenic compounds using a sheepshead minnow cDNA macroarray.	2003 Jan	12735107
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China].	2003 Jan	12708301
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
Preimplantation mouse embryo development as a target of the pesticide methoxychlor.	2003 Jan-Feb	12507662
Effects of exogenous estrogenic agents on pubertal growth and reproductive system maturation in female rhesus monkeys.	2003 Jul	12730626
Resistance status of house flies (Diptera: Muscidae) from southeastern Nebraska beef cattle feedlots to selected insecticides.	2003 Jun	12852649
Evaluation of alternative tactics for management of insecticide-resistant horn flies (Diptera: Muscidae).	2003 Jun	12852633
Methoxychlor modifies the ultradian secretory pattern of prolactin and affects its TRH response.	2003 May	12761465
Analysis of pesticides in water and sediment under different storage conditions using gas chromatography.	2003 May	12712273
Effect of organochlorine pesticides on maturation of starfish and mouse oocytes.	2003 May	12700411
Isolation of four aquatic streptomycetes strains capable of growth on organochlorine pesticides.	2003 Sep	12699931

Patents

Sample Use Guides

In Vivo Use Guide

Use 2 Ibs. of Marlate 50 (50% methoxychlor) in 25 gals. of water. As a spray, wet animals to the skin. Repeat treatment every 3 weeks as needed.

Route of Administration: Topical

In Vitro Use Guide

Rat primary cortical neurons were exposed to 1 or 10 uM methoxychlor for 9 days. GluR2 expression in cultures treated with methoxychlor was decreased significantly to approximately 61% and 56% of that observed in untreated cultures.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:02:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:19 GMT 2023`
Record UNII	RIA79UD69L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHOXYCHLOR

Systematic Name

English

METHOXYCHLOR [MI]

Common Name

English

Methoxychlor [WHO-DD]

Common Name

English

DIMETHOXY-DDT

Common Name

English

1,1,1-TRICHLORO-2,2-BIS(4-METHOXYPHENYL)ETHANE

Systematic Name

English

DIANISYLTRICHLORETHANE

Common Name

English

DMDT

Common Name

English

2,2-BIS(P-METHOXYPHENYL)-1,1,1-TRICHLOROETHANE

Common Name

English

METHOXYCHLOR [MART.]

Common Name

English

NSC-8945

Code

English

1,1'-(2,2,2-TRICHLOROETHYLIDENE)BIS(4-METHOXYBENZENE)

Systematic Name

English

2,2-BIS(P-ANISYL)-1,1,1-TRICHLOROETHANE

Common Name

English

METHOXYCHLOR [ISO]

Common Name

English

METHOXYCHLOR [IARC]

Common Name

English

METHOXYCHLOR [HSDB]

Common Name

English

Classification Tree Code System Code

IARC

Methoxychlor

EPA PESTICIDE CODE

34001