1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane: a flame retardant and androgen receptor agonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 18728 |
| CHEMBL ID | 375107 |
| SCHEMBL ID | 332771 |
| MeSH ID | M0506828 |
| Synonym |
|---|
| 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane |
| 3322-93-8 |
| NCGC00091838-01 |
| einecs 222-036-8 |
| ccris 3743 |
| citex bcl 462 |
| vinylcyclohexene tetrabromide |
| hsdb 6146 |
| brn 1927455 |
| saytex bcl 462 |
| cyclohexane, 1,2-dibromo-4-(1,2-dibromoethyl)- |
| 4-(1,2-dibromoethyl)-1,2-dibromocyclohexane |
| 1-(1,2-dibromoethyl)-3,4-dibromocyclohexane |
| bdbm50199965 |
| CHEMBL375107 , |
| MLS002454355 |
| smr001371982 |
| FT-0666491 |
| NCGC00091838-02 |
| HMS3039D13 |
| unii-502d5q149t |
| 3-05-00-00093 (beilstein handbook reference) |
| bch cyclohexane compound |
| 502d5q149t , |
| dtxsid8024947 , |
| NCGC00258523-01 |
| tox21_200970 |
| cas-3322-93-8 |
| dtxcid204947 |
| AKOS015919789 |
| 1,2-dibromo-4-(1,2-dibromoethyl)-cyclohexane |
| c8h12br4 |
| SCHEMBL332771 |
| 1-(1,2-dibromoethyl)-3,4-dibromocyclohexane [hsdb] |
| PQRRSJBLKOPVJV-UHFFFAOYSA-N |
| mfcd00086864 |
| DS-17528 |
| Q20054503 |
| F11583 |
| AB89760 |
| CS-0186287 |
| PD179167 |
| 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane (tbech) |
| SY102311 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Yet toxicological effects are evident at low exposure concentrations: DBE-DBCH is a proven endocrine disruptor of sex and thyroid hormone pathways, with in vivo toxic effects on reproductive, metabolic, and other endpoints." | ( A review of 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane in the environment and assessment of its persistence, bioaccumulation and toxicity. Bodnaryk, A; Fernie, KJ; Fry, M; Letcher, RJ; Marteinson, SC; Marvin, C; Riddell, N; Tomy, GT, 2021) | 1 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The results indicate that use of the generally accepted standard OECD soil may overestimate accumulation of organic contaminants by earthworms, due to high bioavailability of the contaminants and/or weight loss of the worms in it." | ( Accumulation of polybrominated diphenyl ethers, hexabromobenzene, and 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane in earthworm (Eisenia fetida). Effects of soil type and aging. Andersson, PL; Asamoah, RK; Danielsson, C; Nyholm, JR; van der Wal, L, 2010) | 0.59 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 31.6228 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
| Chain A, HADH2 protein | Homo sapiens (human) | Potency | 39.8107 | 0.0251 | 20.2376 | 39.8107 | AID893 |
| Chain B, HADH2 protein | Homo sapiens (human) | Potency | 39.8107 | 0.0251 | 20.2376 | 39.8107 | AID893 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 50.1187 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| interleukin 8 | Homo sapiens (human) | Potency | 74.9780 | 0.0473 | 49.4806 | 74.9780 | AID651758 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 27.1672 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| TDP1 protein | Homo sapiens (human) | Potency | 20.5962 | 0.0008 | 11.3822 | 44.6684 | AID686979 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 60.8199 | 0.0007 | 14.5928 | 83.7951 | AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 12.9886 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID1259381; AID743040 |
| apical membrane antigen 1, AMA1 | Plasmodium falciparum 3D7 | Potency | 25.1189 | 0.7079 | 12.1943 | 39.8107 | AID720542 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 39.8107 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 39.8107 | 0.0013 | 18.0743 | 39.8107 | AID926; AID938 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 27.8579 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 15.2773 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 68.2410 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 36.5578 | 0.0008 | 17.5051 | 59.3239 | AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 56.4105 | 0.0015 | 30.6073 | 15,848.9004 | AID1224848; AID1224849; AID1259403 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 29.7656 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 44.6684 | 0.0002 | 29.3054 | 16,493.5996 | AID588514 |
| bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 50.1187 | 0.7079 | 36.9043 | 89.1251 | AID504333 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 54.6991 | 0.0237 | 23.2282 | 63.5986 | AID743222 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 38.7089 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895; AID1259385 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 26.2678 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| serine-protein kinase ATM isoform a | Homo sapiens (human) | Potency | 22.3872 | 0.7079 | 25.1119 | 41.2351 | AID485349 |
| chromobox protein homolog 1 | Homo sapiens (human) | Potency | 79.4328 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
| parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 35.4813 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
| potassium voltage-gated channel subfamily H member 2 isoform d | Homo sapiens (human) | Potency | 22.3872 | 0.0178 | 9.6374 | 44.6684 | AID588834 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 44.8735 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| mitogen-activated protein kinase 1 | Homo sapiens (human) | Potency | 19.9526 | 0.0398 | 16.7842 | 39.8107 | AID995 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 66.8242 | 0.0006 | 27.2152 | 1,122.0200 | AID651741 |
| lethal(3)malignant brain tumor-like protein 1 isoform I | Homo sapiens (human) | Potency | 31.6228 | 0.0752 | 15.2253 | 39.8107 | AID485360 |
| geminin | Homo sapiens (human) | Potency | 18.3564 | 0.0046 | 11.3741 | 33.4983 | AID624297 |
| lethal factor (plasmid) | Bacillus anthracis str. A2012 | Potency | 15.8489 | 0.0200 | 10.7869 | 31.6228 | AID912 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 76.5677 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| Rap guanine nucleotide exchange factor 4 | Homo sapiens (human) | Potency | 17.7828 | 3.9811 | 46.7448 | 112.2020 | AID720708 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Androgen receptor | Homo sapiens (human) | IC50 (µMol) | 0.0427 | 0.0000 | 0.8753 | 10.0000 | AID274427 |
| Androgen receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.1630 | 0.0010 | 1.9794 | 14.1600 | AID274425 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID274428 | Activity against human androgen receptor expressed in HepG2 cells assessed as reduction in luciferase signal in presence of 100 uM flutamide at 1 uM after 40 hrs | 2006 | Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25 | Identification of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as an androgen agonist. |
| AID274425 | Displacement of androgen fluormone from rat androgen receptor | 2006 | Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25 | Identification of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as an androgen agonist. |
| AID274426 | Activity against human androgen receptor expressed in HepG2 cells assessed as activation of luciferase reporter gene at 1 uM | 2006 | Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25 | Identification of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as an androgen agonist. |
| AID274429 | Activity against human androgen receptor expressed in HepG2 cells assessed as renilla reporter gene activation in presence of 1 nM DHT at 1 uM after 40 hrs | 2006 | Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25 | Identification of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as an androgen agonist. |
| AID274427 | Activity against human androgen receptor expressed in HepG2 cells assessed as luciferase reporter gene activation | 2006 | Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25 | Identification of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as an androgen agonist. |
| AID274424 | Displacement of androgen fluormone from androgen receptor at 100 uM | 2006 | Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25 | Identification of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane as an androgen agonist. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 6 (17.65) | 29.6817 |
| 2010's | 21 (61.76) | 24.3611 |
| 2020's | 7 (20.59) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (16.40) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (2.94%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 33 (97.06%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||