METHOXYCHLOR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H15Cl3O2
Molecular Weight	345.6485
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COc1ccc(cc1)C(c2ccc(cc2)OC)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	345.6485
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 17 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 3315	15.47 µM [IC50]
Cytochrome P450 2C11 Target ID: CHEMBL4971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 3315	22.45 µM [IC50]
Cytochrome P450 2C6 Target ID: CHEMBL1907986 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 3315	14.84 µM [IC50]
Cytochrome P450 2B6 9 Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10101147	Substrate 261

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lice infestation 3 Sources: https://www3.epa.gov/pesticides/chem_search/ppls/000352-00167-19690424.pdf	Curative		Approved 4033	Marlate Approved Use Applied for the control of certain external parasites.
Flea infestations 4 Sources: https://www3.epa.gov/pesticides/chem_search/ppls/000352-00075-19780918.pdf	Curative		Approved 4033	Marlate Approved Use Applied for the control of certain external parasites.

PubMed

Title	Date	PubMed
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Effect of methoxychlor on antioxidant system of goat epididymal sperm in vitro.	2001 Dec	11753474
Optimization of a yeast estrogen screen and its applicability to study the release of estrogenic isoflavones from a soygerm powder.	2001 Jul	11485867
Effects of nutrient loading and planktivory on the accumulation of organochlorine pesticides in aquatic food chains.	2001 Jun	11392141
Description and evaluation of a short-term reproduction test with the fathead minnow (Pimephales promelas).	2001 Jun	11392137
Mechanism of induction of cytochrome p450 enzymes by the proestrogenic endocrine disruptor pesticide-methoxychlor: interactions of methoxychlor metabolites with the constitutive androstane receptor system.	2001 Jun	11353743
Application of static liquid-phase microextraction to the analysis of organochlorine pesticides in water.	2001 Jun 15	11442045
Inhibition of basal and stimulated progesterone synthesis by dichlorodiphenyldichloroethylene and methoxychlor in a stable pig granulosa cell line.	2001 Mar	11226075
Cell response endpoints enhance sensitivity of the immature mouse uterotropic assay.	2001 May-Jun	11390168
Analysis of organochlorine pesticides in human milk: preliminary results.	2001 Nov	11755050
Response of MCF-7 human breast cancer cells to some binary mixtures of oestrogenic compounds in-vitro.	2001 Nov	11732758
Halogenated organic contaminants in sediments of the Havel and Spree rivers (Germany). Part 5 of organic compounds as contaminants of the Elbe river and its tributaries.	2001 Oct 15	11686361
Differential gene expression in response to methoxychlor and estradiol through ERalpha, ERbeta, and AR in reproductive tissues of female mice.	2001 Sep	11509743
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor.	2002 Apr	11896288
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis.	2002 Apr 15	11969380
Improvement of a two-stage carcinogenesis model to detect modifying effects of endocrine disrupting chemicals on thyroid carcinogenesis in rats.	2002 Apr 8	11849735
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
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
Ethological methods to study the effects of maternal exposure to estrogenic endocrine disrupters: a study with methoxychlor.	2002 Jan-Feb	11836072
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
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
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 primary exposure to environmental and natural estrogens on vitellogenin production in carp (Cyprinus carpio) hepatocytes.	2002 May	11961218
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
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
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

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 `Sat Jun 26 11:24:06 UTC 2021` Edited by `admin` on `Sat Jun 26 11:24:06 UTC 2021`
Record UNII	RIA79UD69L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHOXYCHLOR

Systematic Name

English

METHOXYCHLOR [WHO-DD]

Common Name

English

METHOXYCHLOR [MI]

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