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 8504	15.47 µM [IC50]
Cytochrome P450 2C11 2 Target ID: CHEMBL4971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 8504	22.45 µM [IC50]
Cytochrome P450 2C6 1 Target ID: CHEMBL1907986 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162	Inhibitor 8504	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 6 Sources: https://www3.epa.gov/pesticides/chem_search/ppls/000352-00167-19690424.pdf	Curative		Approved 8583	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 8583	Marlate Approved Use Applied for the control of certain external parasites.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 CYP19A1 429 OATP1B3 961 CYP2C19 2057 CYP1A2 2153	CYP3A5 446 CYP1A2 1197 P-gp 2052 CYP2C19 1119 MRP1 113 CYP2B6 776 CYP2C18 149 CYP1A1 389 CYP2A6 626 CYP1B1 104 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 13.0	inconclusive [IC50 14.0815 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 10.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 2.0	yes [IC50 0.3537 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 3.0	yes [IC50 0.4996 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 14.0	yes [IC50 15.7997 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 27.0	yes [IC50 31.5246 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2MjkxOSJ9fQ==	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2MjkxOSJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 29 \| 303	inconclusive
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	major [Km 0.43 uM]
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	minor
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	minor
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	no
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	no
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	yes [Km 0.51 uM]
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9733665/	yes
MRP1 113	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMDA0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM2MjkxOSJ9fQ==	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/4115#section=Biological-Test-Results Page: 10.0

PubMed

Title	Date	PubMed
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Metabolic activation of bisphenol A by rat liver S9 fraction.	2001 Aug	11452134
An in vitro reporter gene assay method incorporating metabolic activation with human and rat S9 or liver microsomes.	2001 Jan 12	11162482
Determination of pesticides in drinking water by micellar electrokinetic capillary chromatography.	2001 Jul	11504061
Optimization of a yeast estrogen screen and its applicability to study the release of estrogenic isoflavones from a soygerm powder.	2001 Jul	11485867
Insecticide susceptibility in Coptotermes formosanus and Reticulitermes virginicus (Isoptera: Rhinotermitidae).	2001 Oct	11681687
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
Effects of prenatal exposure to low doses of diethylstilbestrol, o,p'DDT, and methoxychlor on postnatal growth and neurobehavioral development in male and female mice.	2001 Sep	11534990
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
Genistein and methoxychlor modulate the activity of natural killer cells and the expression of phenotypic markers by thymocytes and splenocytes in F0 and F1 generations of Sprague-Dawley rats.	2002 Apr 2	11893419
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region.	2002 Aug	12196010
Combined effects of dietary phytoestrogen and synthetic endocrine-active compound on reproductive development in Sprague-Dawley rats: genistein and methoxychlor.	2002 Mar	11861976
Effects of subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects.	2002 May	11961226
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
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China].	2003 Jan	12708301
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
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 `Mon Mar 31 17:36:14 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:14 GMT 2025`
Record UNII	RIA79UD69L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHOXYCHLOR

Systematic Name

English

NSC-8945

Preferred 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

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