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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 of METHOXYCHLOR

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

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

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

Originator

Sources: DOI: 10.1002/prac.18930470103

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
15.4700000000000006 µM [IC50]
22.4499999999999993 µM [IC50]
14.8399999999999999 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Marlate

Approved Use

Applied for the control of certain external parasites.
Curative
Marlate

Approved Use

Applied for the control of certain external parasites.
PubMed

PubMed

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

Sample Use Guides

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
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
  • Download
Name Type Language
METHOXYCHLOR
HSDB   ISO   MART.   MI   WHO-DD  
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
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
Code System Code Type Description
MERCK INDEX
M7331
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
METHOXYCHLOR
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
EPA CompTox
72-43-5
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-779-9
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
PUBCHEM
4115
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
FDA UNII
RIA79UD69L
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
HSDB
1173
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
CAS
72-43-5
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
MESH
D008731
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
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