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Name Description
id 19
T3DB ID T3D0020
Name Chlordane
Class SmallMolecule
Description Chlordane is a manufactured chemical that was used as a pesticide in the United States from 1948 to 1988. Chlordane occurs in two isomers, called cis-chlordane (alpha-chlordane) and trans-chlordane (gamma-chlordane) (L90).
Categories "Pesticide", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Pollutant", "Synthetic Compound"
Synonyms "1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0(2,6)]dec-8-ene", "Alpha-chlordan", "Alpha-chlordane", "Aspon-chlordane", "C orodane", "C-chlordane", "Chlor kill", "Chlordan", "Chlordane-technical", "Chlorindan", "Chlorodane", "Chlorotox", "Chlortox", "Cis-chlordane", "Cis-photochlordane", "Clordan", "Clordano", "Compound k", "Corodane", "Cortilan-neu", "Dichlorochlordene", "Dow-klor", "Dowchlor", "Gold crest", "Intox", "Intox 8", "Kilex lindane", "Kypchlor", "Liquid Chlordane", "Octa-klor", "Octach lorohexahydromethanoindene", "Octachlor", "Octachlordane", "Octachloro-4, 7-methanohydroindane", "Octachloro-4,7-methanohydroindane", "Octachloro-4,7-methanotetrahydroindane", "Octachlorodihydrodicyclopentadiene", "Octachlorohexahydromethanoindene", "Oindane", "Oktaterr", "Ortho-klor", "Photochlordane", "Shell sd-5532", "Starchlor", "Steraskin", "Sydane", "Syndane", "Synklor", "T-chlordane", "Tat Chlor 4", "Technical Chlordane", "Termex", "Termi-ded", "Topichlor 20", "Topiclor", "Topiclor 20", "Toxichlor", "Trans-chlordan", "Trans-chlordane", "Unexan-koeder", "Velsicol 1068"
CAS Number 57-74-9
Chemical Formula C10H6Cl8
Average Molecular Mass 409.78
Monoisotopic Mass 405.80
IUPAC Name 1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.0²,?]dec-8-ene
Traditional Name chlordane
SMILES ClC1CC2C(C1Cl)C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl
InChI Identifier InChI=1/C10H6Cl8/c11-3-1-2-4(5(3)12)9(16)7(14)6(13)8(2,15)10(9,17)18/h2-5H,1H2
InChI Key InChIKey=BIWJNBZANLAXMG-UHFFFAOYNA-N
Kingdom Organic Compounds
Super Class Organohalogen Compounds
Class Vinyl Halides
Sub Class Vinyl Chlorides
Direct Parent Vinyl Chlorides
Alternate Parents "Chloroalkenes", "Organochlorides", "Alkyl Chlorides"
Geometric Description Aliphatic Homopolycyclic Compounds
Substituents "organochloride", "alkyl chloride", "Alkyl Halide", "Aliphatic Homopolycyclic Compound", "Chloroalkene", "Vinyl Chloride", "Haloalkene"
Descriptors "Organochlorine pesticides (KEGG)", "Organochlorine insecticides (KEGG)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cell junction", "Cytoskeleton", "Extracellular", "Membrane", "Membrane Fraction", "Microsome", "Mitochondrion", "Plasma Membrane"
Biofluids
Tissues
Pathways "Apoptosis", "Cell cycle", "Influenza a", "Eicosanoids", "Degradation Of Aromatic Compounds"
State Solid
Appearance Colorless to amber liquid.
Melting Point 106°C
Boiling Point
Solubility 5.6e-05 mg/mL at 25 °C [SANBORN,JR et al. (1976)]
LogP
Route of Exposure Oral (L281) ; inhalation (A105)
Mechanism of Toxicity Chlordane is believed to bind irreversibly to DNA, leading to cell death or altered cellular function. It also affects transcription by antagonizing estrogen-related receptors. Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. Chlordane has also been shown to bind and activate retinoic acid receptor, causing various developmental defects, and inhibit alkaline phosphatases in hepatic and renal tissues. (L91, A52, A53, A68, A69)
Metabolism Chlordane is highly lipophilic and is thus easily absorbed by ingestion, inhalation, and dermal exposure, then stored mainly in the fat. Chlordane is metabolized mainly in the liver and kidney. Metabolism is slow, and is believed to occur by multiple pathways involving cytochrome P-450 enzymes, glutathione-S-transferase type enzymes, and microsomal mixed-function oxidase systems. The metabolites are generally less toxic and include chlordene chlorohydrin, monohydroxylated dihydrochlordene, and oxychlordane. They are excreted in the urine and faeces. (L91)
Toxicity LD50: 200 mg/kg (Oral, Rat) (T13) LD50: 343 mg/kg (Intraperitoneal, Rat) (T13) LD50: 10 mg/kg (Intravenous, Mouse) (T14) LD50: 780 mg/kg (Dermal, Rat) (T14) LC50: 100 mg/m3 over 4 hours (Inhalation, Cat) (T14)
Lethal Dose 100 mg/kg for an adult human. (T15)
Carcinogenicity 2B, possibly carcinogenic to humans. (L135)
Uses/Sources Chlordane was used as a pesticide. (L90)
Minimum Risk Level Intermediate Inhalation: 0.0002 mg/m3 (L134) Chronic Inhalation: 0.00002 mg/m3 (L134) Acute Oral: 0.001 mg/kg/day (L134) Intermediate Oral: 0.0006 mg/kg/day (L134) Chronic Oral: 0.0006 mg/kg/day (L134)
Health Effects Chlordane is a central nervous system stimulant, and can also damage the digestive system and the liver. Large doses have been known to cause convulsions, respiratory failure, and death. Chlordane is also known to have adverse reproductive and developmental effects. (L91)
Symptoms Ingestion and inhalation of chlordane cause headaches, irritability, confusion, weakness, vision problems, vomiting, stomach cramps, diarrhea, and jaundice. (L91)
Treatment Treatment is symptomatic. It is aimed at controlling convulsions, coma, and respiratory depression. Gastric lavage, followed by the administration of activated charcoal, may be performed following ingestion. (L146)
DrugBank ID
HMDB ID
PubChem Compound ID 5993
ChEMBL ID
ChemSpider ID 26563723
KEGG Compound ID C14176
UniProt ID 0
OMIM ID 0
ChEBI ID 34623
BioCyc ID 1-AMINO-PROPAN-2-OL
CTD ID
Stitch ID Chlordane
PDB ID
ACToR ID 271
Wikipedia Link
Creation Date 2009-03-06 18:57:56
Update Date 2014-12-24 20:20:53