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
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
| 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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3397 |
15.47 µM [IC50] | ||
Target ID: CHEMBL4971 |
22.45 µM [IC50] | ||
Target ID: CHEMBL1907986 |
14.84 µM [IC50] | ||
Target ID: CHEMBL4729 |
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. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 11:24:06 UTC 2021
by
admin
on
Sat Jun 26 11:24:06 UTC 2021
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| Record UNII |
RIA79UD69L
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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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
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| Code System | Code | Type | Description | ||
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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
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PRIMARY | Merck Index | ||
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METHOXYCHLOR
Created by
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72-43-5
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200-779-9
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PRIMARY | |||
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4115
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RIA79UD69L
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PRIMARY | |||
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1173
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PRIMARY | |||
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72-43-5
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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
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
