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Toxicology and Applied Pharmacology Jun 1977
Topics: Alanine Transaminase; Animals; Bromobenzenes; Chemical and Drug Induced Liver Injury; Liver; Liver Diseases; Male; Oxidation-Reduction; Rats; Structure-Activity Relationship
PubMed: 882979
DOI: 10.1016/0041-008x(77)90069-2 -
Journal of Labelled Compounds &... Nov 2021Convenient and straightforward synthesis of ibrutinib labeled by carbon-13 isotope is reported. Isotopically labeled building block is introduced in the last step of...
Convenient and straightforward synthesis of ibrutinib labeled by carbon-13 isotope is reported. Isotopically labeled building block is introduced in the last step of reaction sequence affording sufficient isolated yield (7%) of [ C ]-ibrutinib calculated towards starting commercially available [ C ]-bromobenzene.
Topics: Adenine; Bromobenzenes; Carbon Isotopes; Chemistry Techniques, Synthetic; Piperidines; Protein Kinase Inhibitors
PubMed: 34478181
DOI: 10.1002/jlcr.3944 -
IARC Monographs on the Evaluation of... 1990
Review
Topics: Animals; Bromobenzenes; Carcinogens; Chemical Phenomena; Chemistry; Female; Flame Retardants; Halogenated Diphenyl Ethers; Male; Mice; Phenyl Ethers; Polybrominated Biphenyls; Rats
PubMed: 2197464
DOI: No ID Found -
Drug Metabolism and Disposition: the... 1988A series of ortho-substituted bromobenzene derivatives with widely differing hepatotoxicities were investigated for their tendency to undergo oxidative metabolism and...
A series of ortho-substituted bromobenzene derivatives with widely differing hepatotoxicities were investigated for their tendency to undergo oxidative metabolism and protein covalent binding in the presence of rat liver microsomes in vitro. Compounds studied included o-bromobenzonitrile, o-dibromobenzene, bromobenzene, o-bromoanisole, and o-bromotoluene (names in order of decreasing hepatotoxicity and increasing rate of in vitro metabolism). No correlation was found between net covalent binding and toxicity. However, a good rank order correlation was observed between toxicity and the relative binding index of each compounds, defined as (picomoles covalently bound/nmol metabolized), with values ranging from a low of 7 with o-bromotoluene to a high of 365 with o-bromobenzonitrile, Extensive side chain metabolism was observed with o-bromotoluene (92-95%) and o-bromoanisole (26-42%), which accounts for their high rate of total metabolism and low relative binding index. The extent of tritium loss, relative to C-14, was assessed for each compound as an index of the "average oxidation state" of those metabolites, presumably epoxides and/or quinones, which covalently bound to protein. Tritium retention ranged from a high of 84% with o-bromobenzonitrile to a low of 21% with o-bromoanisole, and generally paralleled toxicity. These results show that introduction of ortho-substituents onto bromobenzene leads to qualitative and quantitative changes in overall oxidative metabolism, as well as important qualitative changes in the nature of reactive metabolites formed. Nevertheless, the relative binding index computed for each compound appears to reconcile these changes to a large degree, giving an in vitro index which correlates well with toxicity.
Topics: Animals; Bromobenzenes; Chemical and Drug Induced Liver Injury; Chromatography, High Pressure Liquid; In Vitro Techniques; Male; Microsomes, Liver; Rats
PubMed: 2898339
DOI: No ID Found -
Zhonghua Yu Fang Yi Xue Za Zhi [Chinese... Aug 2018Decabromodiphenyl ethane (DBDPE) is a kind of new brominated flame retardants, which is widely used as a replace of decabromodiphenyl ether in electronic appliances,... (Review)
Review
Decabromodiphenyl ethane (DBDPE) is a kind of new brominated flame retardants, which is widely used as a replace of decabromodiphenyl ether in electronic appliances, textiles and other goods. This review summarizes environmental levels and body burden of human beings of DBDPE in recent years. The data shows that the concentration of DBDPE in the environment and human tissues shows an upward trend. According to limited experiments about its toxicity, DBDPE shows similar toxicity to decabromodiphenyl ether. DBDPE can interfere thyroid hormones balance, and cause damage to liver, reproductive development, kidney, et al, which implies that DBDPE might be another new persistent organic pollutant. Further researches are needed.
Topics: Bromobenzenes; Environmental Pollutants; Flame Retardants; Humans
PubMed: 30107722
DOI: 10.3760/cma.j.issn.0253-9624.2018.08.015 -
Clinical Pharmacokinetics Jun 1999Bromfenac is a nonsteroidal anti-inflammatory drug whose peak plasma concentration is reached 0.5 hours after oral administration. Bromfenac binds extensively to plasma... (Review)
Review
Bromfenac is a nonsteroidal anti-inflammatory drug whose peak plasma concentration is reached 0.5 hours after oral administration. Bromfenac binds extensively to plasma albumin. The area under the plasma concentration-time curve is linearly proportional to the dose for oral doses up to 150 mg. The relationship between the total plasma and analgesic effect has been established. Only small amounts of bromfenac are eliminated unchanged, with the remaining drug being biotransformed into glucuronide metabolites which are excreted in urine and bile. Rapid elimination occurs in healthy individuals (half-life 0.5 to 4.0 h). Renal disease, hepatic disease and aging alter the disposition kinetics of bromfenac, and dosage adjustment may be advisable. Bromfenac modestly decreases free phenytoin concentrations. Bromfenac can cause idiosyncratic hepatic toxicity and has been withdrawn by its manufacturer pending further investigation of these case reports.
Topics: Analgesics; Anti-Inflammatory Agents, Non-Steroidal; Benzophenones; Bromobenzenes; Drug Interactions; Humans
PubMed: 10427465
DOI: 10.2165/00003088-199936060-00002 -
Journal of Agricultural and Food... 1976
Topics: Animals; Bromobenzenes; Feces; Isomerism; Oxidation-Reduction; Rabbits; Structure-Activity Relationship
PubMed: 1254808
DOI: 10.1021/jf60204a001 -
Molecules (Basel, Switzerland) Nov 2007Certain substituted bromobenzenes have been synthesized in acceptable yields using a novel Sandmeyer type reaction. The reactions are relatively quick and possibly...
Certain substituted bromobenzenes have been synthesized in acceptable yields using a novel Sandmeyer type reaction. The reactions are relatively quick and possibly proceed via a radical mechanism.
Topics: Aniline Compounds; Bromine; Bromobenzenes; Models, Chemical; Molecular Structure
PubMed: 18065952
DOI: 10.3390/12112478 -
Toxicology and Applied Pharmacology Jun 1983In this study, freshly prepared isolated rat hepatocytes were exposed to various concentrations of bromobenzene and six ortho-substituted bromobenzenes. Toxicity was... (Comparative Study)
Comparative Study
In this study, freshly prepared isolated rat hepatocytes were exposed to various concentrations of bromobenzene and six ortho-substituted bromobenzenes. Toxicity was estimated by trypan blue dye exclusion and release of GPT and K+ over a 0- to 4-hr time course. In all cases a close correlation among these three indices was observed. The rate of response depended on the exposure level and the nature of the o-substituent. The relative toxicity followed the order C2H5 greater than CH3 greater than or equal to CF3 greater than Br much greater than H greater than OCH3 much greater than CN. This order does not correlate well with the in vivo toxicity data previously obtained in this laboratory (Toranzo E. G., Gillesse, T., Mendenhall, M., Traiger, G.J., Riley, P.G., Hanzlik, R.P., and Wiley, R.A. (1977). Toxicol. Appl. Pharmacol. 40, 415-425.); in fact an almost inverse relationship is indicated. Several possible reasons are proposed in order to rationalize the discrepancy between these two results. The results emphasize the need for caution when using isolated hepatocytes to screen new compounds for purposes of determining their potential in vivo toxicity, at least until the differences between hepatocytes in vivo and hepatocytes in vitro are more thoroughly understood.
Topics: Animals; Bromobenzenes; Dose-Response Relationship, Drug; In Vitro Techniques; Liver; Male; Rats; Rats, Inbred Strains; Structure-Activity Relationship; Time Factors
PubMed: 6857688
DOI: 10.1016/0041-008x(83)90119-9 -
Chemical Research in Toxicology Jun 1997
Review
Topics: Alkylation; Animals; Benzene Derivatives; Benzoquinones; Bromobenzenes; Cytochrome P-450 Enzyme System; Epoxy Compounds; Fungicides, Industrial; Hexachlorobenzene; Oxidation-Reduction; Quinones; Rats
PubMed: 9208168
DOI: 10.1021/tx9601061