T3D0022

23 T3D0022

Hexachlorobutadiene

Hexachlorobutadiene is a man-made chemical primarily produced as a by-product in the production of carbon tetrachloride and tetrachloroethene. It is also used to make rubber compounds, lubricants, in gyroscopes, as a heat transfer liquid, as a hydraulic fluid, and as a solvent. (L93, L94) 87-68-3

6901

C4Cl6

257.813120 Colorless liquid.

-21°C

210-220°C

0.0032 mg/mL at 25 °C [BANERJEE,S et al. (1980)]

Oral (L94); inhalation (L94); dermal (L94)

DNA Transcription factor EC (O14948) Cystathionine beta-synthase (P35520) Hemoglobin subunit alpha (P69905) (A54)

It is believed that intermediates produced by modification of the S- 1,1,2,3,4-pentachlorodienyl cysteine derivative metabolite by gamma-glutamyltransferase are responsible for the observed effects on the proximal tubules of the nephrons. These metabolites uncouple oxidative phosphorylation, preventing the generation of ATP, and also inhibit cytochrome c-cytochrome oxidase activity and electron transport. The carcinogenic properties of hexachlorobutadiene are proposed to result from binding of the sulfenic acid degradation product or a thioketene intermediate to cellular DNA. The binding of hexachlorobutadiene to alpha 2u-globulin is believed to be an important factor in its nephrotoxicity. (L94, A54)

After absorption, most of the hexachlorobutadiene is carried to the liver, where it is metabolized by a glutathione-mediated pathway. It is initially bioactivated to S-glutathione conjugates which may later be metabolized further by beta-lyases and other enzymes. Hexachlorobutadiene and its metabolites preferentially distribute to the kidney, liver, adipose deposits, and possibly the brain. Metabolites are eventually excreted in the urine and faeces. (L94) LD50: 90 mg/kg (Oral, Rat) (T14) LD50: 175 mg/kg (Intraperitoneal, Rat) (T14) LD50: 1211 mg/kg (Dermal, Rabbit) (T14) 3, not classifiable as to its carcinogenicity to humans. (L135)

Hexachlorobutadiene is primarily produced as a by-product in the production of carbon tetrachloride and tetrachloroethene. It is also used to make rubber compounds, lubricants, in gyroscopes, as a heat transfer liquid, as a hydraulic fluid, and as a solvent. (L94)

Intermediate Oral: 0.0002 mg/kg/day (L134)

Hexachlorobutadiene is damaging to the liver and kidney, and may result in fatty liver degeneration, epithelial necrotizing nephritis, central nervous system depression and cyanosis. (L93, L94)

Inhalation of hexachlorobutadiene causes nasal irritation and difficulty breathing. (L94) As there is no antidote for hexachlorobutadiene, exposure is usually treated symptomatically. (L94)

2009-03-06T18:57:56Z

2014-12-24T20:20:54Z

Glutathione S-transferase P (P09211) Glutathione S-transferase Mu 1 (P09488) Glutathione S-transferase A1 (P08263) Glutathione S-transferase theta-2 (P30712) Glutathione S-transferase Mu 4 (Q03013) Glutathione S-transferase theta-1 (P30711) Glutathione S-transferase A4 (O15217) Glutathione S-transferase A2 (P09210) Glutathione S-transferase A3 (Q16772) Glutathione S-transferase Mu 3 (P21266) Glutathione S-transferase omega-1 (P78417) Glutathione S-transferase kappa 1 (Q9Y2Q3) Glutathione S-transferase Mu 2 (P28161) Glutathione S-transferase omega-2 (Q9H4Y5) Glutathione S-transferase A5 (Q7RTV2) Glutathione S-transferase Mu 5 (P46439) Glutathione S-transferase theta-4 (A8MPT4) Maleylacetoacetate isomerase (O43708) Microsomal glutathione S-transferase 1 (P10620) Microsomal glutathione S-transferase 2 (Q99735) Microsomal glutathione S-transferase 3 (O14880) Kynurenine--oxoglutarate transaminase 1 (Q16773) Kynurenine--oxoglutarate transaminase 3 (Q6YP21) Gamma-glutamyltranspeptidase 1 (P19440) Gamma-glutamyltranspeptidase 2 (P36268) Putative gamma-glutamyltranspeptidase 3 (A6NGU5) Gamma-glutamyltransferase 5 (P36269) Gamma-glutamyltransferase 6 (Q6P531) Gamma-glutamyltransferase 7 (Q9UJ14) (L94)

C11091

BUTADIENE

C001335

Hexachlorobutadiene

692

true

ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl

C4Cl6

InChI=1S/C4Cl6/c5-1(3(7)8)2(6)4(9)10

InChIKey=RWNKSTSCBHKHTB-UHFFFAOYSA-N

260.761

257.813116242

Exogenous Liquid

CHEMBL389950

6635