类

SmallMolecule

T3DB_ID

T3D0021

描述

DDE, P,P'- is an isomer of dichlorodiphenyldichloroethylene, an organochlorine insecticide. It is one of the components of commercial mixtures of DDT. DDT was once a widely used pesticide, but today its agricultural use has been banned worldwide due to its toxicity and tendency to bioaccumulate. However, it still has limited use in disease vector control. (L84)

类别

"Pesticide", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"

同义词

"1, 1-Bis(p-chlorophenyl)-2,2-dichloroethylene", "1,1'-(2,2-dichloroethene-1,1-diyl)bis(4-chlorobenzene)", "1,1'-(dichloroethenylidene)bis(4-chloro)-Benzene", "1,1'-(Dichloroethenylidene)bis(4-chlorobenzene)", "1,1'-(Dichloroethenylidene)bis(chloro)-Benzene", "1,1'-(dichloroethenylidene)bis4-chloro-Benzene", "1,1'-(Dichloroethenylidene)bis[4-chlorobenzene]", "1,1'-(dichloroethenylidene)bis[4-chloro]-Benzene", "1,1'-(Dichlorovinylidene)bis(chlorobenzene)", "1,1'-Bis(chlorophenyl)-2,2-dichloroethylene", "1,1-Bis(p-chlorophenyl)-2,2-dichloroethylene", "1,1-dichloro-2, 2-bis(p-chlorophenyl)-Ethylene", "1,1-Dichloro-2, 2-bis(p-chlorophenyl)ethene", "1,1-Dichloro-2, 2-bis(p-chlorophenyl)ethylene", "1,1-Dichloro-2, 2-di(p-chlorophenyl)ethylene", "1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethylene", "1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethylene (DDE)", "1,1-Dichloro-2,2-bis(4-chlorophenyl)ethene", "1,1-Dichloro-2,2-bis(4-chlorophenyl)ethene solution", "1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene", "1,1-Dichloro-2,2-bis(p-chlorophenyl)ethene", "1,1-Dichloro-2,2-Bis(p-chlorophenyl)ethylene", "1,1-Dichloro-2,2-bis(para-chlorophenyl) ethylene", "1,1-Dichloro-2,2-bis[4-chlorophenyl]ethylene", "1,1-Dichloro-2,2-di(p-chlorophenyl)ethylene", "1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene", "1-Chloro-4-[2,2-dichloro-1-(4-chlorophenyl)vinyl]benzene", "2, 2-Bis(4-chlorophenyl)-1,1-dichloroethylene", "2, 2-Bis(p-chlorophenyl)-1,1-dichloroethylene", "2,2-Bis(4-chlorophenyl)-1,1-dichloroethene", "2,2-Bis(4-chlorophenyl)-1,1-dichloroethylene", "2,2-bis(chlorophenyl)-1,1-dichloro-Ethylene", "2,2-Bis(chlorophenyl)-1,1-dichloroethylene", "2,2-bis(p-chlorophenyl)-1,1-dichloroethene", "2,2-Bis(p-chlorophenyl)-1,1-dichloroethylene", "4,4'-DDE", "4,4'-DDE solution", "4,4'-DDEe", "4,4';-DDE solution", "DDE", "DDE(p,p')", "DDT dehydrochloride", "DDX", "Dichlorodiphenyl dichloroethene", "Dichlorodiphenyl dichloroethylene", "Dichlorodiphenyldichloroethylene", "Dichloroethylene, dichlorodiphenyl", "p, p'-(dichlorodiphenyl)dichloroethylene", "p,p'-(Dichlorodiphenyl)-2,2-dichloroethylene", "p,p'-(dichlorodiphenyl)dichloroethylene", "P,P'-dde", "p,p'-DDE", "p,p'-DDE (p,p'-dichlorodiphenyldichloroethylene)", "p,p'-dichlorodiphenoldichloroethylene", "p,p'-dichlorodiphenyl dichloroethylene", "p,p'-dichlorodiphenyldichloroethylene", "p,p'-dichlorodiphenyldichloroethylene (dde)", "p,p-dde", "P,p-dichlorodiphenyldichloroethylene", "Para,para'-DDE"

CAS登记号

72-55-9

化学式

C14H8Cl4

平均分子量

318.025

单同位素质量

315.938011084

IUPAC 名称

1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene

传统名称

p,p'-DDE

简化分子线性输入规范

ClC(Cl)=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1

InChI 标识符

InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H

键

InChIKey=UCNVFOCBFJOQAL-UHFFFAOYSA-N

化合物类型

Organic compounds

大分类

Benzenoids

类型

Benzene and substituted derivatives

子类

Diphenylmethanes

直接大类

Diphenylmethanes

另外分类

"Aryl chlorides", "Chloroalkenes", "Chlorobenzenes", "Hydrocarbon derivatives", "Ketene acetals", "Organochlorides", "Vinyl chlorides"

取代基

"Aromatic homomonocyclic compound", "Aryl chloride", "Aryl halide", "Chloroalkene", "Chlorobenzene", "Diphenylmethane", "Haloalkene", "Halobenzene", "Hydrocarbon derivative", "Ketene acetal or derivatives", "Organochloride", "Organohalogen compound", "Vinyl chloride", "Vinyl halide"

分子框架

Aromatic homomonocyclic compounds

外部描述符

"Organochlorine pesticides", "a small molecule", "chlorophenylethylene", "monochlorobenzenes"

地位

Detected and Not Quantified

起源

Exogenous

蜂窝位置

"Membrane"

生物流体位置

组织位置

途径

状态

Solid

外貌

White powder.

熔点/沸点/溶解度

89°C//4e-05 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

日志P

暴露途径

Oral (L85)

毒性机制

DDE toxicity occurs via at least four mechanisms, possibly all functioning simultaneously. DDE reduces potassium transport across the membrane. DDE inhibits the inactivation of voltaged-gated sodium channels. The channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization and resulting in a state of hyperexcitability. DDE inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. DDE also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. DDE is also believed to adversely affect the reproductive system by mimicking endogenous hormones and binding to the estrogen and adrogen receptors. (T10, L85)

代谢

DDE is absorbed in the stomach and intestine, after which it enters the lymphatic system and is carried throughout the body and incorporated into fatty tissues. Metabolism of DDE occurs mainly via cytochrome P-450 enzymes in the liver and kidney. Its metabolites, mainly DDA (bis(p-chlorophenyl) acetic acid), are excreted in the urine. (L85)

毒性值

致死剂量

致癌性

Not directly listed by IARC, but carcinogenicity studies of this DDT metabolite are discussed in connection with DDT (L2151).

用途/来源

DDE is found in DDT, which is used as a pesticide and in disease vector control. (L84)

最低风险等级

健康影响

Exposure to DDT causes loss of weight and anorexia. DDT poisoning affects CNS function in humans, but pathologic changes are observed in the liver and reproductive organs. Hypertrophy of hepatocytes and subcellular organelles such as mitochondria, proliferation of smooth endoplasmic reticulum, centrolobular necrosis after exposure to high concentrations, and an increase in the incidence of hepatic tumors have been noted. (T10)

症状

Acute signs of DDT poisoning include paresthesia after oral ingestion. Studies have shown that a mammal poisoned with DDT-type agents displays periodic persistent tremoring and/or convulsive seizures that are suggestive of repetitive discharges in neurons. These repetitive tremors and seizures can be initiated by tactile and auditory stimuli. (T10)

治疗

Treatment of DDT exposure should be primarily directed towards decontamination and supportive care, as there is no specific antidote. The use of gastric lavage and activated charcoal for large ingestions may be effective. (L140)

药库 ID

HMDB_ID

PubChem 化合物 ID

3035

维基百科链接

创建于

2009-03-06 18:57:56 UTC

更新于

2014-12-24 20:20:53 UTC

目标

毒素T3DB ID	毒素名称	目标名称
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit epsilon
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit delta
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit beta-3
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit beta-2
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit beta-1
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit alpha-6
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit alpha-5
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit alpha-4
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit alpha-3
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit alpha-2
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit alpha-1
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit theta
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit rho-3
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit rho-2
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit rho-1
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit pi
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit gamma-3
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit gamma-2
T3D0021	P,P'-DDE	Gamma-aminobutyric acid receptor subunit gamma-1
T3D0021	P,P'-DDE	Nuclear receptor subfamily 1 group I member 2
T3D0021	P,P'-DDE	Progesterone receptor
T3D0021	P,P'-DDE	Sodium channel subunit beta-4
T3D0021	P,P'-DDE	Sodium channel subunit beta-3
T3D0021	P,P'-DDE	Sodium channel subunit beta-2
T3D0021	P,P'-DDE	Sodium channel subunit beta-1
T3D0021	P,P'-DDE	Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 3
T3D0021	P,P'-DDE	Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 1
T3D0021	P,P'-DDE	Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4
T3D0021	P,P'-DDE	Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2
T3D0021	P,P'-DDE	Sodium channel protein type 9 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 8 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 7 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 5 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 4 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 3 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 2 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 11 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 10 subunit alpha
T3D0021	P,P'-DDE	Sodium channel protein type 1 subunit alpha
T3D0021	P,P'-DDE	Estrogen receptor beta
T3D0021	P,P'-DDE	Estrogen receptor alpha
T3D0021	P,P'-DDE	Calmodulin
T3D0021	P,P'-DDE	Sarcoplasmic/endoplasmic reticulum calcium ATPase 3
T3D0021	P,P'-DDE	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2
T3D0021	P,P'-DDE	Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
T3D0021	P,P'-DDE	Plasma membrane calcium-transporting ATPase 4
T3D0021	P,P'-DDE	Plasma membrane calcium-transporting ATPase 3
T3D0021	P,P'-DDE	Plasma membrane calcium-transporting ATPase 2
T3D0021	P,P'-DDE	Plasma membrane calcium-transporting ATPase 1
T3D0021	P,P'-DDE	Calcium-transporting ATPase type 2C member 2
T3D0021	P,P'-DDE	Calcium-transporting ATPase type 2C member 1
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit gamma
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit beta-3
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit beta-2
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit beta-1
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit alpha-4
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit alpha-3
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit alpha-2
T3D0021	P,P'-DDE	Sodium/potassium-transporting ATPase subunit alpha-1
T3D0021	P,P'-DDE	Androgen receptor