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
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
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26961610
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162 |
15.47 µM [IC50] | ||
Target ID: CHEMBL4971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162 |
22.45 µM [IC50] | ||
Target ID: CHEMBL1907986 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833162 |
14.84 µM [IC50] | ||
Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10101147 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Marlate Approved UseApplied for the control of certain external parasites. |
|||
Curative | Marlate Approved UseApplied for the control of certain external parasites. |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 13.0 |
inconclusive [IC50 14.0815 uM] | |||
Page: 10.0 |
no | |||
Page: 2.0 |
yes [IC50 0.3537 uM] | |||
Page: 3.0 |
yes [IC50 0.4996 uM] | |||
Page: 14.0 |
yes [IC50 15.7997 uM] | |||
Page: 27.0 |
yes [IC50 31.5246 uM] | |||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 29 | 303 |
inconclusive | |||
major [Km 0.43 uM] | ||||
minor | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 0.51 uM] | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 10.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
Metabolic activation of bisphenol A by rat liver S9 fraction. | 2001 Aug |
|
An in vitro reporter gene assay method incorporating metabolic activation with human and rat S9 or liver microsomes. | 2001 Jan 12 |
|
Determination of pesticides in drinking water by micellar electrokinetic capillary chromatography. | 2001 Jul |
|
Optimization of a yeast estrogen screen and its applicability to study the release of estrogenic isoflavones from a soygerm powder. | 2001 Jul |
|
Insecticide susceptibility in Coptotermes formosanus and Reticulitermes virginicus (Isoptera: Rhinotermitidae). | 2001 Oct |
|
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 |
|
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 |
|
Differential gene expression in response to methoxychlor and estradiol through ERalpha, ERbeta, and AR in reproductive tissues of female mice. | 2001 Sep |
|
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor. | 2002 Apr |
|
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis. | 2002 Apr 15 |
|
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 |
|
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region. | 2002 Aug |
|
Combined effects of dietary phytoestrogen and synthetic endocrine-active compound on reproductive development in Sprague-Dawley rats: genistein and methoxychlor. | 2002 Mar |
|
Effects of subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects. | 2002 May |
|
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 |
|
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China]. | 2003 Jan |
|
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 |
|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26961610
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
Edited
Mon Mar 31 17:36:14 GMT 2025
by
admin
on
Mon Mar 31 17:36:14 GMT 2025
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Record UNII |
RIA79UD69L
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
---|---|---|---|---|
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IARC | Methoxychlor | ||
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EPA PESTICIDE CODE |
34001
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m7331
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METHOXYCHLOR
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