ContaminantDB: Endosulfan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (49)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:59 UTC

Update Date

2017-04-05 00:25:10 UTC

Accession Number

CHEM000050

Identification

Common Name

Endosulfan

Class

Small Molecule

Description

Endosulfan is a organochlorine insecticide and acaricide. The two isomers, endo and exo, are known popularly as I and II. Endosulfan sulfate is a product of oxidation containing one extra O atom attached to the S atom. It is used to control insects on food and non-food crops and also as a wood preservative. Due to its toxicity and tendency to bioaccumulate, the use of endosulfan is banned in many areas. (4)

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Herbicide
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dimethanol cyclic sulfite	ChEBI
1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenedimethyl sulphite	ChEBI
1,9,10,11,12,12-Hexachloro-4,6-dioxa-5-thiatricyclo[7.2.1.0(2,8)]dodec-10-ene 5-oxide	ChEBI
alpha,beta-1,2,3,4,7,7-Hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulfite	ChEBI
Benzoepin	ChEBI
1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dimethanol cyclic sulphite	Generator
1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenedimethyl sulfite	Generator
a,b-1,2,3,4,7,7-Hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulfite	Generator
a,b-1,2,3,4,7,7-Hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulphite	Generator
alpha,beta-1,2,3,4,7,7-Hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulphite	Generator
Α,β-1,2,3,4,7,7-hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulfite	Generator
Α,β-1,2,3,4,7,7-hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulphite	Generator
endoSulphan	Generator
Thiotox	MeSH, HMDB
Thiodan	MeSH, HMDB
beta-Endosulfan	MeSH, HMDB
Thiodon	MeSH, HMDB
alpha Endosulfan	MeSH, HMDB
alpha-Endosulfan	MeSH, HMDB
beta Endosulfan	MeSH, HMDB

Chemical Formula

C₉H₆Cl₆O₃S

Average Molecular Mass

406.925 g/mol

Monoisotopic Mass

403.817 g/mol

CAS Registry Number

115-29-7

IUPAC Name

1,9,10,11,12,12-hexachloro-4,6-dioxa-5λ⁴-thiatricyclo[7.2.1.0²,⁸]dodec-10-en-5-one

Traditional Name

endosulfan

SMILES

ClC1=C(Cl)C2(Cl)C3COS(=O)OCC3C1(Cl)C2(Cl)Cl

InChI Identifier

InChI=1S/C9H6Cl6O3S/c10-5-6(11)8(13)4-2-18-19(16)17-1-3(4)7(5,12)9(8,14)15/h3-4H,1-2H2

InChI Key

RDYMFSUJUZBWLH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sulfite esters. These are organic compounds containing an organic group attached to the sulfite oxoanion, with the formula R[SO3]2-.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic sulfites

Direct Parent

Sulfite esters

Alternative Parents

Substituents

Sulfite ester
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclic sulfite ester (CHEBI:4791 )
cyclodiene organochlorine insecticide (CHEBI:4791 )
Organochlorine pesticides (C11090 )
Organochlorine insecticides (C11090 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Actin Cytoskeleton
Cell junction
Cytoskeleton
Cytosol
Endoplasmic reticulum
Extracellular
Lysosome
Membrane
Membrane Fraction
Microsome
Mitochondrial Matrix
Mitochondrion
Nucleolus
Peroxisome
Plasma Membrane
Ribosome
Sarcoplasmic Reticulum
Secretory vesicle

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Proteasome	Not Available	Not Available
Oxidative phosphorylation	Not Available	map00190
Ovarian Steroidogenesis	Not Available	Not Available
Cell cycle	Not Available	map04110
Antiviral Agents	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Cream- to brown-colored solid.

Experimental Properties

Property	Value
Melting Point	106°C
Boiling Point	Not Available
Solubility	0.000325 mg/mL at 22 °C [TOMLIN,C (1994)]

Predicted Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	4.32	ALOGPS
logP	2.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.98 m³·mol⁻¹	ChemAxon
Polarizability	31.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6839000000-c9547e9129c46466e951	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0001900000-14803a5488f7b5642868	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009000000-c53d9213cf67e512f24a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fy9-3019000000-b61f370914dcbdd006e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0001900000-4a6457e8c8712884b840	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-1009700000-1f6854b3041bccaaf5b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2009000000-0d683166427dc5b15175	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-2eefcdeb338309d303ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000900000-2eefcdeb338309d303ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0108900000-cbd073f44cae72c878ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-e2d19f5f0adc47d59a36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000900000-62f46a28d1c6ad7c7173	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ue9-4000900000-3f8af71ab3b467356262	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kn-2691000000-d66e2736219436d73395	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; inhalation (5) ; dermal (5)

Mechanism of Toxicity

Endosulfan antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions. Endosulfan also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the CNS. This results in hyperexcitation and generalized seizures. Endosulfan is also an endocrine disruptor and acts as an agonist at the progesterone receptor and estrogen receptors. (8, 4, 5, 1, 3)

Metabolism

Endosulfan is absorbed by inhalation, oral, and dermal routes of exposure. It accumulates mainly in the liver, kidney, and brain, and is metabolized to polar and nonpolar metabolites by cytochrome P-450 enzymes. Endosulfan and its metabolites, which include sulfate, diol, α-hydroxyether, lactone, and ether derivatives of endosulfan, are excreted in the urine and faeces. (5)

Toxicity Values

LD50: 18 mg/kg (Oral, Rat) (9) LD50: 34 mg/kg (Dermal, Rat) (9) LD50: 8 mg/kg (Intraperitoneal, Rat) (9) LD50: 360 mg/kg (Subcutaneous, Rabbit) (9) LC50: 80 mg/m3 over 4 hours (Inhalation, Rat) (9)

Lethal Dose

50 to 500 mg/kg for an adult human. (10)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Endosulfan is used as an insecticide, acaricide, and in wood preservatives. (5)

Minimum Risk Level

Intermediate Oral: 0.005 mg/kg/day (6) Chronic Oral: 0.002 mg/kg/day (6)

Health Effects

Endosulfan is a neurotoxin and damages the central nervous system, causing effects such as intermittent muscle twitching and myoclonic jerking. Endosulfan can also damage the kidneys, testes, and liver, and may possibly affect the body's ability to fight infection. It is also an endocrine disruptor and causes reproductive and developmental damage. (8, 4, 5)

Symptoms

Symptoms of endosulfan poisoning include hyperactivity, hyperreflexia, tremors, dizziness, headache, convulsions, lack of coordination, staggering, difficulty breathing, nausea and vomiting, diarrhea, and in severe cases, unconsciousness. (8, 4, 5)

Treatment

Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (7)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0251793

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Endosulfan (CHEM000050)

Structure for CHEM000050: Endosulfan