U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of METHOXYCHLOR

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

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

CNS Penetrant
2523
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.

Originator

Elbs, K.
1
Sources: DOI: 10.1002/prac.18930470103

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 15.47 µM [IC50]
Inhibitor
8228
 22.45 µM [IC50]
Inhibitor
8228
 14.84 µM [IC50]
Substrate
656
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8360
Marlate

Approved Use

Applied for the control of certain external parasites.
Curative
Approved
8360
Marlate

Approved Use

Applied for the control of certain external parasites.
PubMed

PubMed

TitleDatePubMed
Methoxychlor stimulates the mouse lactoferrin gene promoter through a GC-rich element.
2002
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor.
2002 Apr
Assessment of interactions of diverse ternary mixtures in an estrogen receptor-alpha reporter assay.
2002 Apr 1
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis.
2002 Apr 15
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region.
2002 Aug
Methoxychlor may cause ovarian follicular atresia and proliferation of the ovarian epithelium in the mouse.
2002 Aug
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
Determination of organochlorine pesticides in seawater using liquid-phase hollow fibre membrane microextraction and gas chromatography-mass spectrometry.
2002 Aug 30
Analysis of pesticides and PCB congeners in serum by GC/MS with SPE sample cleanup.
2002 Aug 5
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.
2002 Dec
Determination of estrogenic activity in landfill leachate by simplified yeast two-hybrid assay.
2002 Dec
An avian bioassay for environmental estrogens: the growth response of zebra finch (Taeniopygia guttata) chick oviduct to oral estrogens.
2002 Dec
Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents.
2002 Dec
Induction of oxidative stress in the rat testis after short-term exposure to the organochlorine pesticide methoxychlor.
2002 Dec
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
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
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
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
Is exposure to endocrine disrupting compounds during fetal/post-natal development affecting the reproductive potential of farm animals?
2002 Jul
Effect of methoxychlor on the antioxidant system in mitochondrial and microsome-rich fractions of rat testis.
2002 Jul 1
Detection of estrogenic activity in sediment-associated compounds using in vitro reporter gene assays.
2002 Jul 3
Methoxychlor alters the predator-prey relationship between dragonfly naiads and salamander larvae.
2002 Jun
Thyroid toxicity due to subchronic exposure to a complex mixture of 16 organochlorines, lead, and cadmium.
2002 Jun
Organochlorine pesticides directly regulate gonadotropin-releasing hormone gene expression and biosynthesis in the GT1-7 hypothalamic cell line.
2002 Jun 28
The effect of methoxychlor on the epididymal antioxidant system of adult rats.
2002 Mar-Apr
Comparative assessment of endocrine modulators with oestrogenic activity. II. Persistent organochlorine pollutants.
2002 May
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
Effects of subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects.
2002 May
Effects of primary exposure to environmental and natural estrogens on vitellogenin production in carp (Cyprinus carpio) hepatocytes.
2002 May
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.
2002 Nov
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
Effect of tolerance to insecticides on substrate penetration by Formosan subterranean termites (Isoptera: Rhinotermitidae).
2002 Oct
A comparison of the estrogenic potencies of estradiol, ethynylestradiol, diethylstilbestrol, nonylphenol and methoxychlor in vivo and in vitro.
2002 Oct 2
Thymic atrophy induced by methoxychlor in rat pups.
2002 Oct 5
Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: pathways involving a novel catechol metabolite.
2002 Sep
The rat as a model in developmental immunotoxicology.
2002 Sep-Oct
Environmental estrogens alter early development in Xenopus laevis.
2003 Apr
The multidrug resistance-associated protein 1 transports methoxychlor and protects the seminiferous epithelium from injury.
2003 Apr 30
Inhibition of gonadotropin-induced oviposition and ovarian steroidogenesis in the African clawed frog (Xenopus laevis) by the pesticide methoxychlor.
2003 Feb 12
Expression profiling of estrogenic compounds using a sheepshead minnow cDNA macroarray.
2003 Jan
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China].
2003 Jan
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Preimplantation mouse embryo development as a target of the pesticide methoxychlor.
2003 Jan-Feb
Effects of exogenous estrogenic agents on pubertal growth and reproductive system maturation in female rhesus monkeys.
2003 Jul
Resistance status of house flies (Diptera: Muscidae) from southeastern Nebraska beef cattle feedlots to selected insecticides.
2003 Jun
Evaluation of alternative tactics for management of insecticide-resistant horn flies (Diptera: Muscidae).
2003 Jun
Methoxychlor modifies the ultradian secretory pattern of prolactin and affects its TRH response.
2003 May
Analysis of pesticides in water and sediment under different storage conditions using gas chromatography.
2003 May
Effect of organochlorine pesticides on maturation of starfish and mouse oocytes.
2003 May
Isolation of four aquatic streptomycetes strains capable of growth on organochlorine pesticides.
2003 Sep
Patents

Patents

JP2011506740A
1
JP2011509971A
151
JPH04261147A
2
JPH0640818A
2

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 Wed Jul 05 22:34:23 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:23 UTC 2023
Record UNII
RIA79UD69L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOXYCHLOR
HSDB   ISO   MART.   MI   WHO-DD  
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
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
Code System Code Type Description
MERCK INDEX
M7331
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
METHOXYCHLOR
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID9020827
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
CHEBI
6842
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-779-9
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
DAILYMED
RIA79UD69L
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
ALANWOOD
methoxychlor
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
NSC
8945
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
PUBCHEM
4115
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
FDA UNII
RIA79UD69L
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
HSDB
1173
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
CAS
72-43-5
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
RXCUI
2598123
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
SMS_ID
100000184171
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
MESH
D008731
Created by admin on Wed Jul 05 22:34:23 UTC 2023 , Edited by admin on Wed Jul 05 22:34:23 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2A6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of HYDROXYCHLOR
METABOLITE -> PARENT
Structure of 4-(2,2,2-TRICHLORO-1-(4-METHOXYPHENYL)ETHYL)-1,2-BENZENEDIOL
METABOLITE -> PARENT
Structure of MONODEMETHYLMETHOXYCHLOR
METABOLITE -> PARENT
Structure of 4-(2,2,2-TRICHLORO-1-(4-HYDROXYPHENYL)ETHYL)-1,2-BENZENEDIOL
METABOLITE -> PARENT
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966