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Name Description
id 82
T3DB ID T3D0093
Name Hexachlorobenzene
Class SmallMolecule
Description Hexachlorobenzene is an agricultural fungicide, belonging to the family of Chlorobenzenes. These are compounds containing a chlorine atom attached to a benzene moiety.
Categories "Pesticide", "Pollutant", "Airborne Pollutant", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Aromatic Hydrocarbon", "Pesticide", "Pollutant", "Food Toxin", "Metabolite", "Synthetic Compound"
Synonyms "1,2,3,4,5,6-Hexachloro-Benzene", "1,2,3,4,5,6-Hexachlorobenzene", "Amatin", "Ceku c.b.", "Co-op hexa", "Esaclorobenzene", "Granox", "Granox NM", "HCB", "Hexa c.b", "Hexa c.b.", "Hexa CB", "Hexachlorbenzol", "Hexachloro-Benzene", "Julen's carbon chloride", "Pentachlorophenyl chloride", "Perchlorobenzene", "Phenyl perchloryl", "S Anocide", "Sanocid", "Sanocide", "Smut-go", "Snieciotox", "Voronit c"
CAS Number 118-74-1
Chemical Formula C6Cl6
Average Molecular Mass 284.78
Monoisotopic Mass 281.81
IUPAC Name hexachlorobenzene
Traditional Name hexachlorobenzene
SMILES ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl
InChI Identifier InChI=1S/C6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9
InChI Key InChIKey=CKAPSXZOOQJIBF-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Halobenzenes
Direct Parent Chlorobenzenes
Alternate Parents "Aryl Chlorides", "Organochlorides"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "chlorobenzene", "aryl chloride", "organochloride", "Aromatic Homomonocyclic Compound", "Aryl Halide", "Organohalogen Compound"
Descriptors "chlorobenzenes (ChEBI)", "Organochlorine fungicides (KEGG)"
Status Detected and Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids "Blood"
Tissues
Pathways
State Solid
Appearance White powder.
Melting Point 226°C
Boiling Point 323-326°C
Solubility 6.2e-06 mg/mL at 25°C
LogP 5.73
Route of Exposure Oral (L225); inhalation (L225) ; dermal (L225)
Mechanism of Toxicity Hexachlorobenzene causes porphyria by modifying sulfhydryl groups in the catalytic or substrate-binding sites of uroporphyrinogen decarboxylase. This inhibits uroporphyrinogen decarboxylase, resulting in a deficiency of the decarboxylation of uroporphyrinogen III and accumulation of uroporphyrins in the liver. In addition, metabolism of hexachlorobenzene by the cytochrome P-450 enzymes is believed to produce reactive electrophilic metabolites that covalently bind to cellular proteins and DNA, causing irreversible damage. Exposure to hexochlorobenzene also causes macrophages to be attracted to organs such as the spleen, lungs, and skin, where they become activated by the hexochlorobenzene. This leads to a cascade of reactions involving innate immune cells. The gene expression profiles provide evidence for the importance of macrophages and granulocytes and mediators released by these cells in the adverse inflammatory response against hexochlorobenzene. In this way, co-stimulatory or danger signals are generated that could polyclonally activate T cells. Hexachlorobenzene is a weak agonist for aryl hydrocarbon receptor and may exhibit some of its toxic effects by activating the gene-regulatory properties of this protein, possibly inducing cytochome P-450 enzymes. It may also act at certain endocrine receptors. (A14, L225, A156, A157, A60)
Metabolism Hexachlorobenzene is mainly absorbed via ingestion, but also through inhalation and oral routes. It preferentially distributes to adipose tissue and other organs with high fat content. In animals, hexachlorobenzene is slowly metabolized to pentachlorophenol by the hepatic cytochrome P-450 system, conjugated with glutathione to yield pentachlorothiophenol, or reductively dechlorinated to form pentachlorobenzene. Other metabolites include less chlorinated benzenes, chlorophenols, S-conjugated phenols, and benzenes. Hexachlorobenzene is slowly metabolized in mammals, and the majority of hexachlorobenzene is excreted unchanged in the feces, while metabolites are excreted in the urine. (L225)
Toxicity LD50: 3500 mg/kg (Oral, Rat) (T10)
Lethal Dose
Carcinogenicity 2B, possibly carcinogenic to humans. (L135)
Uses/Sources Hexachlorobenzene was previously used as a pesticide to protect the seeds of onions and sorghum, wheat, and other grains against fungus. It was also used to make fireworks, ammunition, and synthetic rubber. As it can persist in the environment for long periods of time, today exposure occurs mainly from contact with contaminated water, food, soil, or air. (L225)
Minimum Risk Level Acute Oral: 0.008 mg/kg/day (L134) Intermediate Oral: 0.0001 mg/kg/day (L134) Chronic Oral: 0.00005 mg/kg/day (L134)
Health Effects Chronic exposure to hexachlorobenzene can damage the liver, thyroid, nervous system, bones, kidneys, blood, and immune and endocrine systems. It also causes a syndrome, called black sore, that is characterized by dermal blistering and epidermolysis, pigmentation and scarring, alopecia, photosensitivity, hepatomegaly, porphyria, suppurative arthritis, osteomyelitis, and osteoporosis of the bones of the hands. It may also cause a liver disease called porphyria cutanea tarda. This disease can cause red-colored urine, skin sores, change in skin color, arthritis, and problems of the liver, nervous system, and stomach. Hexachlorobenzene also affects development and results in lower survival rates of children of exposed mothers. It is also believed to be a human carcinogen. (T10, L225)
Symptoms Hexachlorobenzene causes a syndrome, called black sore, that is characterized by dermal blistering and epidermolysis, pigmentation and scarring, alopecia, photosensitivity, hepatomegaly, porphyria, suppurative arthritis, osteomyelitis, and osteoporosis of the bones of the hands. It may also cause a liver disease called porphyria cutanea tarda. This disease can cause red-colored urine, skin sores, change in skin color, arthritis, and problems of the liver, nervous system, and stomach. (L225)
Treatment Treatment is mainly symptomatic and may include gastric lavage, administering activated charcoal, and controlling convulsions. (L226)
DrugBank ID
HMDB ID HMDB32566
PubChem Compound ID 8370
ChEMBL ID CHEMBL228514
ChemSpider ID 8067
KEGG Compound ID C11042
UniProt ID 0
OMIM ID 0
ChEBI ID 5692
BioCyc ID CPD-1125
CTD ID D006581
Stitch ID Hexachlorobenzene
PDB ID
ACToR ID 691
Wikipedia Link
Creation Date 2009-03-06 18:58:04
Update Date 2014-12-24 20:21:05