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
Acute hepatotoxicity of DDT: effect on glucocorticoid receptors and serum transcortin.
2000 May
Anaerobic bioventing of unsaturated zone contaminated with DDT and DNT.
2001
Distribution of DDT residues in fish from the Songkhla Lake, Thailand.
2001
Mixtures of four organochlorines enhance human breast cancer cell proliferation.
2001 Apr
Analyses of lindane, vinclozolin, aldrin, p,p'-DDE, o,p'-DDT and p,p'-DDT in human serum using gas chromatography with electron capture detection and tandem mass spectrometry.
2001 Aug 25
Gas exchange of OCPs across the air-water interface at the creek adjoining Mumbai harbour, India.
2001 Dec
Surfactant-enhanced solubilization and anaerobic biodegradation of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)-ethane (DDT) in contaminated soil.
2001 Jan-Feb
Modulatory effects of neonatal exposure to TCDD, or a mixture of PCBs, p,p'-DDT, and p-p'-DDE, on methylnitrosourea-induced mammary tumor development in the rat.
2001 Jul
Optimization of a yeast estrogen screen and its applicability to study the release of estrogenic isoflavones from a soygerm powder.
2001 Jul
Organochlorine pesticides, polychlorinated biphenyls, and butyltin compounds in blubber and livers of stranded California sea lions, elephant seals, and harbor seals from coastal California, USA.
2001 Jul
Sex-associated expression of mouse hepatic and renal CYP2B enzymes by glucocorticoid hormones.
2001 Jul 15
Determination of organochlorine pesticides and chlorobenzenes in strawberries by using accelerated solvent extraction combined with sorptive enrichment and gas chromatography/mass spectrometry.
2001 Jul-Aug
Differing effects of endocrine-disrupting chemicals on basal and FSH-stimulated progesterone production in rat granulosa-luteal cells.
2001 Jun
The global distribution of PCBs and organochlorine pesticides in butter.
2001 Mar 15
Plasma levels of persistent organohalogens and hormone levels in adult male humans.
2001 Mar-Apr
Anaerobic biodegradation of DDT residues (DDT, DDD, and DDE) in estuarine sediment.
2001 May
Effects of environmental antiandrogens on reproductive development in experimental animals.
2001 May-Jun
Relationship between two consecutive lactations and fat level in persistent organochlorine compound concentrations in human breast milk.
2001 May-Jun
Association of DDT with spontaneous abortion: a case-control study.
2001 Oct
Organochlorines and 8-hydroxy-2'-deoxyguanosine (8-OHdG) in cancerous and noncancerous breast tissue: do the data support the hypothesis that oxidative DNA damage caused by organochlorines affects breast cancer?
2001 Oct
Identification of a novel class of insect glutathione S-transferases involved in resistance to DDT in the malaria vector Anopheles gambiae.
2001 Oct 15
Determination of DDT and its metabolites in cattle dip soil available in aqueous phase after remediation.
2001 Sep
Current levels of DDT, PCB and trace elements in the Baltic ringed seals (Phoca hispida baltica) and grey seals (Halichoerus grypus).
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
Differential expression and induction of two Drosophila cytochrome P450 genes near the Rst(2)DDT locus.
2002 Aug
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
Dichlorodiphenyltrichloroethane in soil, river sediment, and fish in the Amazon in Brazil.
2002 Feb
A molecular motif required for the activation of rat neutrophil phospholipase A(2) by organochlorine compounds.
2002 Feb
Hair analysis: another approach for the assessment of human exposure to selected persistent organochlorine pollutants.
2002 Jan
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
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
Residuals of beta-hexachlorocyclohexane, dichlorodiphenyltrichloroethane, and hexachlorobenzene in serum, and relations with consumption of dietary components in rural residents in Japan.
2002 Mar 8
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
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.
2002 Sep
Evidence for a stabilizer element in the untranslated regions of Drosophila glutathione S-transferase D1 mRNA.
2002 Sep 20
Great tit (Parus major) nestlings as biomonitors of organochlorine pollution.
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 GMT 2023
Edited
by admin
on Sat Dec 16 15:52:50 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
WHO-VATC QP53AB51
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
WHO-ATC P03AB01
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
NCI_THESAURUS C737
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
NCI_THESAURUS C45386
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
WHO-ATC P03AB51
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
Code System Code Type Description
FDA UNII
CIW5S16655
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
WIKIPEDIA
DDT
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
HSDB
200
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
DRUG BANK
DB13424
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
MERCK INDEX
m4113
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY Merck Index
EVMPD
SUB06700MIG
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
SMS_ID
100000084311
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
PUBCHEM
3036
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
NCI_THESAURUS
C44364
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
MESH
C493852
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
CHEBI
16130
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
ALANWOOD
DDT
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
CAS
50-29-3
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
MESH
D003634
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL416898
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-024-3
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
INN
2202
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
DRUG CENTRAL
4396
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
NSC
8939
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID4020375
Created by admin on Sat Dec 16 15:52:50 GMT 2023 , Edited by admin on Sat Dec 16 15:52:50 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY