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 48 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 7701	15.4700000000000006 µM [IC50]
Cytochrome P450 2C11 2 Target ID: CHEMBL4971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 7701	22.4499999999999993 µM [IC50]
Cytochrome P450 2C6 1 Target ID: CHEMBL1907986 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 7701	14.8399999999999999 µM [IC50]
Cytochrome P450 2B6 19 Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10101147	Substrate 609

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 7997	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 7997	Marlate Approved Use Applied for the control of certain external parasites.

PubMed

Title	Date	PubMed
Interaction of methoxychlor and related compounds with estrogen receptor alpha and beta, and androgen receptor: structure-activity studies.	2000 Oct	10999957
Determination of pesticides in drinking water by micellar electrokinetic capillary chromatography.	2001 Jul	11504061
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Inhibition of basal and stimulated progesterone synthesis by dichlorodiphenyldichloroethylene and methoxychlor in a stable pig granulosa cell line.	2001 Mar	11226075
Diet and organochlorine contaminants in women of reproductive age under 40 years old.	2001 Nov	11755049
Insecticide susceptibility in Coptotermes formosanus and Reticulitermes virginicus (Isoptera: Rhinotermitidae).	2001 Oct	11681687
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
Determination of organochlorine pesticides in seawater using liquid-phase hollow fibre membrane microextraction and gas chromatography-mass spectrometry.	2002 Aug 30	12236503
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
Utility of a juvenile fathead minnow screening assay for detecting (anti-)estrogenic substances.	2002 Feb	11833800
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002 Jul	12224631
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
Organochlorine pesticides directly regulate gonadotropin-releasing hormone gene expression and biosynthesis in the GT1-7 hypothalamic cell line.	2002 Jun 28	12088877
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.	2002 Nov	12389925
Effect of tolerance to insecticides on substrate penetration by Formosan subterranean termites (Isoptera: Rhinotermitidae).	2002 Oct	12403426
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
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
Resistance status of house flies (Diptera: Muscidae) from southeastern Nebraska beef cattle feedlots to selected insecticides.	2003 Jun	12852649
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 `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