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
Isolation of four aquatic streptomycetes strains capable of growth on organochlorine pesticides.	2003-09	12699931
Effects of exogenous estrogenic agents on pubertal growth and reproductive system maturation in female rhesus monkeys.	2003-07	12730626
Resistance status of house flies (Diptera: Muscidae) from southeastern Nebraska beef cattle feedlots to selected insecticides.	2003-06	12852649
Evaluation of alternative tactics for management of insecticide-resistant horn flies (Diptera: Muscidae).	2003-06	12852633
Methoxychlor modifies the ultradian secretory pattern of prolactin and affects its TRH response.	2003-05	12761465
Analysis of pesticides in water and sediment under different storage conditions using gas chromatography.	2003-05	12712273
Effect of organochlorine pesticides on maturation of starfish and mouse oocytes.	2003-05	12700411
The multidrug resistance-associated protein 1 transports methoxychlor and protects the seminiferous epithelium from injury.	2003-04-30	12765240
Environmental estrogens alter early development in Xenopus laevis.	2003-04	12676604
The pesticide methoxychlor given orally during the perinatal/juvenile period, reduced the spermatogenic potential of males as adults by reducing their Sertoli cell number.	2003-03-11	12625421
Inhibition of gonadotropin-induced oviposition and ovarian steroidogenesis in the African clawed frog (Xenopus laevis) by the pesticide methoxychlor.	2003-02-12	12560167
Preimplantation mouse embryo development as a target of the pesticide methoxychlor.	2003-01-01	12507662
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003-01-01	12464242
Expression profiling of estrogenic compounds using a sheepshead minnow cDNA macroarray.	2003-01	12735107
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China].	2003-01	12708301
The rat as a model in developmental immunotoxicology.	2002-12-03	12458909
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.	2002-12	12623674
Determination of estrogenic activity in landfill leachate by simplified yeast two-hybrid assay.	2002-12	12509063
An avian bioassay for environmental estrogens: the growth response of zebra finch (Taeniopygia guttata) chick oviduct to oral estrogens.	2002-12	12463562
Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents.	2002-12	12460799
Induction of oxidative stress in the rat testis after short-term exposure to the organochlorine pesticide methoxychlor.	2002-12	12451445
Enantioselective metabolism of the endocrine disruptor pesticide methoxychlor by human cytochromes P450 (P450s): major differences in selective enantiomer formation by various P450 isoforms.	2002-12	12433799
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.	2002-11	12389925
Thymic atrophy induced by methoxychlor in rat pups.	2002-10-05	12270678
A comparison of the estrogenic potencies of estradiol, ethynylestradiol, diethylstilbestrol, nonylphenol and methoxychlor in vivo and in vitro.	2002-10-02	12204590
Effect of tolerance to insecticides on substrate penetration by Formosan subterranean termites (Isoptera: Rhinotermitidae).	2002-10	12403426
Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: pathways involving a novel catechol metabolite.	2002-09	12167570
Determination of organochlorine pesticides in seawater using liquid-phase hollow fibre membrane microextraction and gas chromatography-mass spectrometry.	2002-08-30	12236503
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.	2002-08-15	12217638
Analysis of pesticides and PCB congeners in serum by GC/MS with SPE sample cleanup.	2002-08-05	12191885
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region.	2002-08	12196010
Methoxychlor may cause ovarian follicular atresia and proliferation of the ovarian epithelium in the mouse.	2002-08	12151644
Detection of estrogenic activity in sediment-associated compounds using in vitro reporter gene assays.	2002-07-03	12109482
Effect of methoxychlor on the antioxidant system in mitochondrial and microsome-rich fractions of rat testis.	2002-07-01	12062931
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002-07	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.	2002-07	12222155
Enhancing effects of beta-estradiol 3-benzoate but not methoxychlor on the promotion/progression stage of chemically-induced mammary carcinogenesis in ovariectomized rats.	2002-07	12149140
Is exposure to endocrine disrupting compounds during fetal/post-natal development affecting the reproductive potential of farm animals?	2002-07	12142238
Organochlorine pesticides directly regulate gonadotropin-releasing hormone gene expression and biosynthesis in the GT1-7 hypothalamic cell line.	2002-06-28	12088877
Methoxychlor alters the predator-prey relationship between dragonfly naiads and salamander larvae.	2002-06	12012050
Thyroid toxicity due to subchronic exposure to a complex mixture of 16 organochlorines, lead, and cadmium.	2002-06	12011480
Comparative assessment of endocrine modulators with oestrogenic activity. II. Persistent organochlorine pollutants.	2002-05	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.	2002-05	11994791
Effects of subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects.	2002-05	11961226
Effects of primary exposure to environmental and natural estrogens on vitellogenin production in carp (Cyprinus carpio) hepatocytes.	2002-05	11961218
The effect of methoxychlor on the epididymal antioxidant system of adult rats.	2002-04-17	11955947
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis.	2002-04-15	11969380
Assessment of interactions of diverse ternary mixtures in an estrogen receptor-alpha reporter assay.	2002-04-01	11922773
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor.	2002-04	11896288
Methoxychlor stimulates the mouse lactoferrin gene promoter through a GC-rich element.	2002	11908639

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