2,4,5,2',4',5'-hexabromobiphenyl profile

2,4,5,2',4',5'-hexabromobiphenyl, also known as hexabromobiphenyl (HBB), is a highly brominated polybrominated biphenyl (PBB) compound. It is a persistent organic pollutant (POP) with a complex synthesis pathway, often involving the reaction of benzene with bromine in the presence of a catalyst. HBB has been extensively studied due to its environmental persistence, bioaccumulation potential, and its potential for adverse health effects. It has been shown to be toxic to various organisms, including humans, causing developmental, reproductive, and endocrine disruptions. HBB's persistence in the environment and its potential to bioaccumulate in food chains makes it a significant environmental concern. Research on HBB aims to understand its fate and transport in the environment, its toxicological profile, and potential remediation strategies.'

2,4,5,2',4',5'-hexabromobiphenyl: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2,2',4,4',5,5'-hexabromobiphenyl : A polybromobiphenyl that is biphenyl in which the hydrogens at positions 2, 2', 4, 4', 5, and 5' have been replace by bromines. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	42948
CHEBI ID	134050
SCHEMBL ID	26724
MeSH ID	M0070247

Synonym
67774-32-7
2,2',4,4',5,5'-hexabromobiphenyl
2,2'4,4'5,5'-hexabromo-1,1'-biphenyl
brn 1991358
hsdb 2913
2,4,5,2',4',5'-hexabromobiphenyl
2,2',4,4',5,5'-hexabromo-1,1'-biphenyl
2,2'4,4',5,5'-hexabromo-1,1'-biphenyl
ccris 5773
1,1'-biphenyl, 2,2',4,4',5,5'-hexabromo-
59080-40-9
pbb 153
pbb153
pbb-153
inchi=1/c12h4br6/c13-7-3-11(17)9(15)1-5(7)6-2-10(16)12(18)4-8(6)14/h1-4
firemaster ff-1
CHEBI:134050
2,2',4,4',5,5'-hexabromo[biphenyl]
1,2,4-tribromo-5-(2,4,5-tribromophenyl)benzene
9s2pwx7kbn ,
unii-9s2pwx7kbn
2,4,5,2',4',5'-hexabromobiphenyl [hsdb]
SCHEMBL26724
HMBBJSKXDBUNNT-UHFFFAOYSA-N
DTXSID70858838
bb 153 (2,2',4,4',5,5'-hexabromobiphenyl)
pbb-no. 153 10 microg/ml in cyclohexane
2,2,4,4,5,5-hexabromobiphenyl
firemaster ff 1.
Q26840910
pbb-no. 153 100 microg/ml in isooctane
pbb-no. 153
1ST6406
2,2',4,4',5,5'-hexabromo biphenyl

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" This is most likely due to the effect of 2,4,5-HBB and toxic congeners formed during the irradiation of 2,4,5-HBB."	( Photolysis products of 2,4,5,2',4',5'-hexabromobiphenyl: hepatic microsomal enzyme induction and toxicity in Sprague-Dawley rats. Aust, SD; Millis, CD; Mills, R; Sleight, SD, 1985)	0.58
" In some HBB-exposed fetuses there were minor abnormalities of brain development, which were probably indicative of developmental delay rather than direct toxic effects on differentiation of specific regions of the brain."	( Placental transfer and developmental toxicity of 2,2',4,4',5,5'-hexabromobiphenyl in B6C3F1 mice. Morgan, KT; Welsch, F, 1985)	0.27
" According to the 24-h acute toxicity test, up to concentration of 210 microg/L, these chemicals were not toxic to Daphnia."	( Comparison of toxicity of congener-153 of PCB, PBB, and PBDE to Daphnia magna. Huhtala, S; Nakari, T, 2008)	0.35

Bioavailability

Excerpt	Reference	Relevance
" Each of the PBB analogs was found in all tissues examined but varied in both rate of absorption and clearance."	( Differential tissue distribution of various polybrominated biphenyls of Firemaster FF-1 in male rats. Domino, EF; Domino, SE; Fivenson, DP, )	0.13

Dosage Studied

Excerpt	Relevance	Reference
" At the end of the dosing period no alterations in the content and profile of the hepatic porphyrins were observed."	( 2,2',4,4',5,5'-hexabromobiphenyl: its toxicokinetics, biotransformation and porphyrinogenic action in rats. Koss, G; Seubert, A; Seubert, S; Weider, T, 1994)	0.29
" Additionally, we identified dose-response curves for serum PBB-153 levels and the prevalence of autoimmune disorders that differed by lifestage of exposure and sex."	( Polybrominated biphenyls (PBBs) and prevalence of autoimmune disorders among members of the Michigan PBB registry. Barr, DB; Barton, H; Hood, RB; Marcus, M; Marder, ME; Mardovich, S; Pearson, M; Somers, EC; Terrell, ML; Tomlinson, MS, 2023)	0.91

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Class	Description
polybromobiphenyl	A biphenyl compound containing between 2 and 10 bromine atoms attached to the two benzene rings.
brominated flame retardant	Any organobromine compound that is used as a flame retardant. These chemicals are widely incorporated as additives in consumer products such as electronics, vehicles, polyurethane foams etc, to make them less flammable.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	19 (45.24)	18.7374
1990's	3 (7.14)	18.2507
2000's	5 (11.90)	29.6817
2010's	8 (19.05)	24.3611
2020's	7 (16.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.13%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	46 (97.87%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	1.96	1	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.37	2	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
decabromobiphenyl ether decabromobiphenyl ether: a flame retardant. decabromodiphenyl ether : A polybromodiphenyl ether that is diphenyl ether in which all of the hydrogens have been replaced by bromines.	2.6	1	polybromodiphenyl ether	neurotoxin
pcb 118 [no description available]	2.13	1	dichlorobenzene; pentachlorobiphenyl; trichlorobenzene
3,4,5,3',4',5'-hexachlorobiphenyl [no description available]	1.96	1	hexachlorobiphenyl; trichlorobenzene
2,4,5,2',4',5'-hexachlorobiphenyl [no description available]	2.79	3	hexachlorobiphenyl
2,2',3',4,4',5-hexachlorobiphenyl [no description available]	2.13	1	polychlorobiphenyl
pcb 180 PCB 180: C12-H3-Cl7	2.13	1	polychlorobiphenyl
2,3,4,5,3',4',5'-heptachlorobiphenyl 2,3,4,5,3',4',5'-heptachlorobiphenyl: induces cytochromes P-448 & P-450; RN given refers to cpd with locants for chlorine moieties	1.96	1	heptachlorobiphenyl; tetrachlorobenzene; trichlorobenzene
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	1.96	1
2,2',4,4'-tetrabromodiphenyl ether [no description available]	2.6	1	aromatic ether; organobromine compound
3,3',4,4',5,5'-hexabromobiphenyl [no description available]	4.31	6
3,3',4,4'-tetrabromobiphenyl [no description available]	1.96	1
firemaster bp-6 [no description available]	2.37	2
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.42	2
nadp [no description available]	2.36	2
octabromobiphenyl octabromobiphenyl: fire retardant; 27858-07-7 (cpd with unspecified bromine locants)	1.96	1
bilirubin [no description available]	2.6	1	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
oligonucleotides [no description available]	2.02	1
lucifer yellow lucifer yellow: RN given refers to di-Li salt	1.97	1	organic lithium salt	fluorochrome
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.02	1

Condition	Relationship Strength	Studies
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.6	1
Abdominal Obesity [description not available]	2.6	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.6	1
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	2.6	1
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.6	1
Autoimmune Disease [description not available]	2.6	1
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	2.6	1
Innate Inflammatory Response [description not available]	2.6	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.6	1
Delayed Effects, Prenatal Exposure [description not available]	2.25	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.68	3
Degenerative Diseases, Central Nervous System [description not available]	2.21	1
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.21	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.88	4
Cancer of Liver [description not available]	1.97	1
Liver Neoplasms Tumors or cancer of the LIVER.	1.97	1
Experimental Hepatoma [description not available]	3.29	2
Condition, Preneoplastic [description not available]	1.96	1
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	1.96	1
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	2.88	1
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	1.96	1
Fetal Resorption The disintegration and assimilation of the dead FETUS in the UTERUS at any stage after the completion of organogenesis which, in humans, is after the 9th week of GESTATION. It does not include embryo resorption (see EMBRYO LOSS).	1.96	1
Keratoderma Blennorrhagicum [description not available]	1.96	1
Keratosis Any horny growth such as a wart or callus.	1.96	1

2,4,5,2',4',5'-hexabromobiphenyl

Description

Cross-References

Synonyms (34)

Research Excerpts

Toxicity

Bioavailability

Dosage Studied

Drug Classes (2)

Research

Studies (42)

Market Indicators

Research Demand Index: 10.97

Study Types

2,4,5,2',4',5'-hexabromobiphenyl

Description

Cross-References

Synonyms (34)

Research Excerpts

Toxicity

Bioavailability

Dosage Studied

Drug Classes (2)

Research

Studies (42)

Market Indicators

Research Demand Index: 10.97

Study Types

Related Drugs (21)

Related Conditions (24)