Page last updated: 2024-12-06

1,2,3,4,5,6-hexabromocyclohexane

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

## 1,2,3,4,5,6-Hexabromocyclohexane: A Versatile Chemical with Research Significance

1,2,3,4,5,6-Hexabromocyclohexane (HBC) is an organic compound, specifically a cyclohexane with six bromine atoms attached to each carbon atom in the ring. This saturated structure grants it a high degree of stability.

Here's why HBC is important for research:

**1. Flame Retardant:** HBC is a highly effective flame retardant. It acts by releasing bromine radicals during combustion, interrupting the chain reaction that propagates fire. This property makes it valuable for use in polymers, plastics, textiles, and electronics.

**2. Synthesis Intermediate:** HBC's structure and reactivity make it a versatile intermediate in organic synthesis. It can be used to create other compounds with unique properties, particularly in the synthesis of cyclic and acyclic brominated compounds.

**3. Physical Properties Research:** The highly symmetrical structure and high bromine content of HBC make it an interesting model compound for studies in physical chemistry. It exhibits unique physical properties such as high density, low vapor pressure, and strong intermolecular interactions. These properties make it suitable for research on crystallography, spectroscopy, and phase transitions.

**4. Environmental Studies:** HBC is a persistent organic pollutant (POP), meaning it breaks down very slowly in the environment. This persistence can lead to bioaccumulation in organisms and poses potential environmental risks. Research on HBC helps understand its environmental fate, degradation pathways, and the potential for remediation.

**5. Biomedical Research:** Although HBC is not currently used in medicine, its unique structure and potential for modification makes it an interesting target for potential drug development. Researchers explore its interaction with biological systems, potentially leading to new applications in treatment of various diseases.

**However, it's crucial to note the drawbacks:**

* **Toxicity:** HBC exhibits toxicity, especially to aquatic life, and has been linked to reproductive and developmental problems in animals.
* **Environmental Persistence:** Its slow degradation and potential for bioaccumulation raises concerns about its impact on the environment.
* **Regulation:** Due to its toxicity and persistence, HBC is regulated in many countries. This can limit its use and research in certain areas.

Overall, 1,2,3,4,5,6-hexabromocyclohexane is a unique compound with valuable properties for research. However, its potential risks must be carefully considered, and its applications should be assessed with caution. Research on HBC aims to understand its properties, find safer alternatives, and develop new uses for this versatile chemical.

Cross-References

ID SourceID
PubMed CID74603
CHEMBL ID444236
CHEBI ID93940
SCHEMBL ID459442
MeSH IDM0484326

Synonyms (40)

Synonym
benzene hexabromide
HMS3268H22
cyclohexane, 1,2,3,4,5,6-hexabromo-
AKOS015836040
cyclohexane,2,3,4,5,6-hexabromo-
nsc7908
1837-91-8
nsc-7908
jak2 inhibitor ii
1,2,3,4,5,6-hexabromocyclohexane ,
NCGC00092358-01
H0368
1,2,3,4,5,6-hexabromo-cyclohexane
CHEMBL444236
A812818
1,2,3,4,5,6-hexakis(bromanyl)cyclohexane
FT-0633875
S5902
BRD-K06817181-001-01-5
DTXSID4052687
SCHEMBL459442
QFQZKISCBJKVHI-UHFFFAOYSA-N
1,2,3,4,5,6-hexabromocyclohexane #
HB1428
c6h6br6
mfcd00059127
CHEBI:93940
1,2,3,4,5,6-hexabromocyclohexane, >=98% (hplc)
J-011778
Q27165694
jak2 inhibitor ii - cas 1837-91-8
HMS3677C10
HMS3413C10
1,2,3,4,5,6-hexabromocyclohexane;nsc7908
NCGC00092358-02
T71979
1,2,3,4,5,6-hexabrom-cyclohexan (i(2)-form)
HY-107594
BAA83791
CS-0028930

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitorAn EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
[role 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]

Drug Classes (2)

ClassDescription
bromohydrocarbonA compound derived from a hydrocarbon by replacing a hydrogen atom with a bromine atom.
bromoalkaneAny haloalkane that consists of an alkane substituted by at least one bromine atom.
[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]

Protein Targets (29)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency25.11890.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency25.11890.025120.237639.8107AID886
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
Chain A, Ferritin light chainEquus caballus (horse)Potency28.18385.623417.292931.6228AID485281
15-lipoxygenase, partialHomo sapiens (human)Potency39.81070.012610.691788.5700AID887
phosphopantetheinyl transferaseBacillus subtilisPotency79.43280.141337.9142100.0000AID1490
Microtubule-associated protein tauHomo sapiens (human)Potency16.81590.180013.557439.8107AID1460; AID1468
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency19.95260.011212.4002100.0000AID1030
mitogen-activated protein kinase 1Homo sapiens (human)Potency39.81070.039816.784239.8107AID995
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency6.47760.00798.23321,122.0200AID2546; AID2551
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency15.84890.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency19.95260.316212.765731.6228AID881
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency19.95260.00638.235039.8107AID881
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID360729Inhibition of human JAK2 V617F mutant expressed in COS7 cells2007The Journal of biological chemistry, Feb-09, Volume: 282, Issue:6
Erlotinib effectively inhibits JAK2V617F activity and polycythemia vera cell growth.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (50.00)29.6817
2010's3 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.74 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]