U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H9Cl5
Molecular Weight 354.486
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOFENOTANE

SMILES

ClC1=CC=C(C=C1)C(C2=CC=C(Cl)C=C2)C(Cl)(Cl)Cl

InChI

InChIKey=YVGGHNCTFXOJCH-UHFFFAOYSA-N
InChI=1S/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H

HIDE SMILES / InChI

Molecular Formula C14H9Cl5
Molecular Weight 354.486
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

DDT (dichlorodiphenyltrichloroethane) is a colorless, crystalline, tasteless and almost odorless organochloride known for its insecticidal properties and environmental impacts. First synthesized in 1874, DDT's insecticidal action was discovered by the Swiss chemist Paul Hermann Müller in 1939. It was used in the second half of World War II to control malaria and typhus among civilians and troops. After the war, DDT was also used as an agricultural insecticide and its production and use duly increased. The United States banned the use of DDT in 1972, but some countries still use the chemical. In December 2000, in a convention organized by the United Nations Environment Program, 122 nations agreed to a treaty banning twelve very toxic chemicals. Included among the twelve was DDT. However, the treaty allowed the use of DDT to combat malaria until other alternatives become available. Before it can take effect the treaty must be ratified by 50 of the nations that agreed to it in principle. DDT has also been used in the past for the treatment of lice. It is still in use outside the United States for the control of mosquitoes that spread malaria. DDT and related chemicals persist for a long time in the environment and in animal tissues. People are most likely to be exposed to DDT from food, including meat, fish, and dairy products. DDT can be absorbed by eating, breathing, or touching products contaminated with DDT. In the body, DDT is converted into several metabolic products, including the metabolite dichlorodiphenyldichloroethene (DDE). DDT and DDE are stored in the body’s fatty tissues. In pregnant women DDT and DDE can be passed to the fetus. Both chemicals are found in breast milk, resulting in exposure to nursing infants. Human health effects from DDT at low environmental doses are unknown. However, following exposure to high doses human symptoms can include vomiting, tremors or shakiness, and seizures. Laboratory animal studies showed effects on both the liver and reproduction. DDT is considered a possible human carcinogen. DDE acts as a weak androgen receptor antagonist, but not as an estrogen. p,p'-DDT, DDT's main component, has little or no androgenic or estrogenic activity. The minor component o,p'-DDT has weak estrogenic activity.

Originator

Curator's Comment: in 1874 by Othmar Zeidler under the supervision of Adolf von Baeyer

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
PubMed

PubMed

TitleDatePubMed
[Effect of nonsteroidal estrogen-like substances on aromatase activity].
2001 May-Jun
Isolation and characterisation of organochlorine pesticides residues from landfill sites.
2001 Oct
Organochlorine pesticide residues in sediments and biota from the coastal area of Dar es Salaam city, Tanzania.
2002
Composition and distribution of organochlorine pesticide residues in surface sediments from the Wu-Shi River Estuary, Taiwan.
2002
Organochlorine pesticide residues in catfish, Tachysurus thalassinus (Ruppell, 1835), from the South Patches of the Bay of Bengal.
2002
Current levels of DDT, PCB and trace elements in the Baltic ringed seals (Phoca hispida baltica) and grey seals (Halichoerus grypus).
2002
Stable chlorine intramolecular kinetic isotope effects from the abiotic dehydrochlorination of DDT.
2002
Bioconcentration of trace organochlorine pesticides by the rainbow trout.
2002
Persistent chlorinated pesticides and polychlorinated biphenyls in selected fish species from Lake Tanganyika, Burundi, Africa.
2002
Intraspecific variation in trophic feeding levels and organochlorine concentrations in glaucous gulls (Larus hyperboreus) from Bjørnøya, the Barents Sea.
2002 Apr
Hepatic microsomal cytochrome p450s and chlorinated hydrocarbons in largha and ribbon seals from Hokkaido, Japan: differential response of seal species to Ah receptor agonist exposure.
2002 Apr
Seasonal variation of persistent organochlorine accumulation in birds from Lake Baikal, Russia, and the role of the south Asian region as a source of pollution for wintering migrants.
2002 Apr 1
Toxic contaminants and their biological effects in coastal waters of Xiamen, China. I. Organic pollutants in mussel and fish tissues.
2002 Aug
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region.
2002 Aug
Differential expression and induction of two Drosophila cytochrome P450 genes near the Rst(2)DDT locus.
2002 Aug
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
Burden of organochlorine pesticides in blood and its effect on thyroid hormones in women.
2002 Aug 5
Isomer-specific activity of dichlorodyphenyltrichloroethane with estrogen receptor in adult and suckling estrogen reporter mice.
2002 Dec
[Bioindication of organochlorine pesticides by night heron in Taihu wetland ecosystem].
2002 Feb
Association of maternal blood pressure and hemoglobin level with organochlorines in human milk.
2002 Jan
Distribution and fate of organochlorine pesticide residues in sediments from the selected rivers in Taiwan.
2002 Jul
Organochlorine chemical residues in fish from the Mississippi River basin, 1995.
2002 Jul
Induction and inhibition of aromatase (CYP19) activity by various classes of pesticides in H295R human adrenocortical carcinoma cells.
2002 Jul 1
Factors influencing nominal effective concentrations of chemical compounds in vitro: medium protein concentration.
2002 Jun
Impact of protein binding on the availability and cytotoxic potency of organochlorine pesticides and chlorophenols in vitro.
2002 Jun 14
DDT inhibits the functional activation of murine macrophages and decreases resistance to infection by Mycobacterium microti.
2002 Jun 5
Membrane-contaminant interaction found by 3D force field calculations.
2002 Mar
Dissolved organic carbon--contaminant interaction descriptors found by 3D force field calculations.
2002 Mar
Distribution of organobrominated and organochlorinated contaminants in Belgian human adipose tissue.
2002 Mar
The organochlorine pesticide residues and antioxidant enzyme activities in human breast tumors: is there any association?
2002 Mar
Effects of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)-ethane (p,p'-DDT) on 3T3-L1 and 3T3-F442A adipocyte differentiation.
2002 Mar 1
Headspace solid-phase microextraction in combination with gas chromatography and tandem mass spectrometry for the determination of organochlorine and organophosphorus pesticides in whole numan blood.
2002 Mar 25
Effect of molecular structures on the solubility enhancement of hydrophobic organic compounds by environmental amphiphiles.
2002 May
Residential pesticide use during pregnancy among a cohort of urban minority women.
2002 May
Associations between weight loss-induced changes in plasma organochlorine concentrations, serum T(3) concentration, and resting metabolic rate.
2002 May
Detailed low-dose study of 1,1-bis(p-chlorophenyl)-2,2,2- trichloroethane carcinogenesis suggests the possibility of a hormetic effect.
2002 May 1
Comparative investigation of multiple organs of mice and rats in the comet assay.
2002 May 27
Persistent organochlorine residues and their bioaccumulation profiles in resident and migratory birds from North Vietnam.
2002 Oct
Biosorption of organochlorine pesticides using fungal biomass.
2002 Oct
Organochlorine hydrocarbons in human breast milk collected in Hong Kong and Guangzhou.
2002 Oct
Persistent organochlorine pollutants in human serum of 50-65 years old women in the Flanders Environmental and Health Study (FLEHS). Part 1: Concentrations and regional differences.
2002 Sep
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.
2002 Sep
Assessing the estrogenic potential of organochlorine pesticides in primary cultures of male rainbow trout (Oncorhynchus mykiss) hepatocytes using vitellogenin as a biomarker.
2002 Sep 16
Evidence for a stabilizer element in the untranslated regions of Drosophila glutathione S-transferase D1 mRNA.
2002 Sep 20
A single p450 allele associated with insecticide resistance in Drosophila.
2002 Sep 27
Pesticides in surface water, sediment, and rainfall of the northeastern Pantanal basin, Brazil.
2002 Sep-Oct
Lipophil-mediated reduction of toxicants in humans: an evaluation of an ayurvedic detoxification procedure.
2002 Sep-Oct
Great tit (Parus major) nestlings as biomonitors of organochlorine pollution.
2003 Jan
Metabolism of DDT [1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane] by Alcaligenes denitrificans ITRC-4 under aerobic and anaerobic conditions.
2003 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:52:50 UTC 2023
Edited
by admin
on Sat Dec 16 15:52:50 UTC 2023
Record UNII
CIW5S16655
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DDT
HPUS   HSDB   ISO   MI  
Preferred Name English
CLOFENOTANE
INN   MART.   WHO-DD  
INN  
Official Name English
P,P'-DDT
Common Name English
DDT, P,P'-
Common Name English
DDT [HPUS]
Common Name English
4,4'-DDT
Common Name English
1,1'-(2,2,2-TRICHLOROETHYLIDENE)BIS(4-CHLOROBENZENE)
Systematic Name English
NSC-8939
Code English
DICOPHANE
Common Name English
DDT [ISO]
Common Name English
CHLOROPHENOTHANE
Common Name English
clofenotane [INN]
Common Name English
Clofenotane [WHO-DD]
Common Name English
DDT [HSDB]
Common Name English
DDT [MI]
Common Name English
1,1,1-TRICHLORO-2,2-BIS(P-CHLOROPHENYL)ETHANE
Common Name English
ENT-1506
Code English
DDT-
Common Name English
CLOFENOTANE [MART.]
Common Name English
1,1,1-TRICHLORO-2,2-BIS(4-CHLOROPHENYL)ETHANE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QP53AB01
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
WHO-VATC QP53AB51
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
WHO-ATC P03AB01
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
NCI_THESAURUS C737
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
NCI_THESAURUS C45386
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
WHO-ATC P03AB51
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
Code System Code Type Description
FDA UNII
CIW5S16655
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
WIKIPEDIA
DDT
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
HSDB
200
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
DRUG BANK
DB13424
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
MERCK INDEX
m4113
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY Merck Index
EVMPD
SUB06700MIG
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
SMS_ID
100000084311
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
PUBCHEM
3036
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
NCI_THESAURUS
C44364
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
MESH
C493852
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
CHEBI
16130
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
ALANWOOD
DDT
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
CAS
50-29-3
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
MESH
D003634
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
ChEMBL
CHEMBL416898
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-024-3
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
INN
2202
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
DRUG CENTRAL
4396
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
NSC
8939
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID4020375
Created by admin on Sat Dec 16 15:52:50 UTC 2023 , Edited by admin on Sat Dec 16 15:52:50 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY