62
T3D0061
Methoxychlor
Methoxychlor is a manufactured organochlorine used as an insecticide against flies, mosquitoes, cockroaches, chiggers, and a wide variety of other insects. It is used on agricultural crops and livestock, and in animal feed, barns, grain storage bins, home garden, and on pets. (L167)
72-43-5
4115
C16H15Cl3O2
344.013760
Pale-yellow powder.
87°C
decomposes
0.0001 mg/mL at 25 °C [RICHARDSON,LT & MILLER,DM (1960)]
Oral (L167) ; dermal (L167)
Sodium/potassium-transporting ATPase subunit alpha-1 (P05023)
Sodium/potassium-transporting ATPase subunit alpha-2 (P50993)
Sodium/potassium-transporting ATPase subunit alpha-3 (P13637)
Sodium/potassium-transporting ATPase subunit alpha-4 (Q13733)
Sodium/potassium-transporting ATPase subunit beta-1 (P05026)
Sodium/potassium-transporting ATPase subunit beta-2 (P14415)
Sodium/potassium-transporting ATPase subunit beta-3 (P54709)
Sodium/potassium-transporting ATPase gamma chain (P54710)
Calcium-transporting ATPase type 2C member 1 (P98194)
Calcium-transporting ATPase type 2C member 2 (O75185)
Plasma membrane calcium-transporting ATPase 1 (P20020)
Plasma membrane calcium-transporting ATPase 2 (Q01814)
Plasma membrane calcium-transporting ATPase 3 (Q16720)
Plasma membrane calcium-transporting ATPase 4 (P23634)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (O14983)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (P16615)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 3 (Q93084)
(T10)
Certain mono- and bis-hydroxy metabolites of methoxychlor, especially 2,2-bis(p-hydroxyphenyl)-1,1, 1-trichloroethane (HPTE), act as estrogen analogues. HPTE is an estrogen receptor alpha agonist, and also acts as an antagonist at the estrogen receptor beta and androgen receptor. This affects protein synthesis, which is believed to cause many of methoxychlor's estrogenic effects, such as decreased fertility. As methoxychlor is also a structural analogue of DDT, it is believed to have the same neurotoxic effects. This includes preventing the deactivation of the sodium gate after neuron activation and membrane depolarization, resulting in hyperexcitability of the nerve. Like DDT, methoxychlor may also inhibit neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase and Ca2+-ATPase, which play vital roles in neuronal repolarization. This contributes to the reduced rate of depolarization and increases the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. (T10, A118)
Methoxychlor is well absorbed by the gastrointestinal tract and to a lesser extent by the skin. Once in the bloodstream, methoxychlor appears to distribute to most tissues of the body, with highest levels usually found in fat. Methoxychlor is metabolized rapidly by cytochrome P450 enzymes in the liver, undergoing demethylation to form phenolic derivatives, with dechlorination and dehydrochlorination reactions occurring to a lesser extent. The metabolites of methoxychlor are excreted mainly in the faeces. (L167)
LD50: 3460 mg/kg (Oral, Rat) (L167)
6400 mg/kg for an adult human. (T28)
3, not classifiable as to its carcinogenicity to humans. (L135)
Methoxychlor is used as an insecticide against flies, mosquitoes, cockroaches, chiggers, and a wide variety of other insects. It is used on agricultural crops and livestock, and in animal feed, barns, grain storage bins, home garden, and on pets. (L167)
Intermediate Oral: 0.005 mg/kg/day (L134)
Animal studies show that methoxychlor may affect the reproductive system, causing harm to the ovaries, uterus, and mating cycle in females, and the testes and prostate in males, as well as decreased fertility in both sexes. Methoxychlor exposure may also cause EEG pattern changes. (T10. L167)
High levels of methoxychlor may cause fatigue, lethargy, tremors, convulsions and seizures. (T10, L167)
2009-03-06T18:58:00Z
2014-12-24T20:21:00Z
Cytochrome P450 2C19 (P33261)
Cytochrome P450 1A2 (P05177)
Cytochrome P450 2A6 (P11509)
Cytochrome P450 2C9 (P11712)
Cytochrome P450 2B6 (P20813)
Cytochrome P450 2D6 (P10635)
Cytochrome P450 2E1 (P05181)
Cytochrome P450 3A4 (P08684)
(L167)
http://en.wikipedia.org/wiki/Methoxychlor
C11043
6842
D008731
Methoxychlor
843
true
Cytochrome P450 2C19 (P33261)
Cytochrome P450 1A2 (P05177)
Cytochrome P450 2A6 (P11509)
Cytochrome P450 2C9 (P11712)
Cytochrome P450 2B6 (P20813)
Cytochrome P450 2D6 (P10635)
Cytochrome P450 2E1 (P05181)
Cytochrome P450 3A4 (P08684)
(L167)
COC1=CC=C(C=C1)C(C1=CC=C(OC)C=C1)C(Cl)(Cl)Cl
C16H15Cl3O2
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
InChIKey=IAKOZHOLGAGEJT-UHFFFAOYSA-N
345.648
344.013762845
Exogenous
Solid
CHEMBL362919
3972