Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: EC:3.2.1.31 (beta-glucuronidase)
 7,680 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

10 excretory products of Clofedanol (1-(o-chlorphenyl)-1-phenyl-3-dimethylaminopropanol) were identified in human urine. The following five products were extracted with chloroform at pH 1--2: o-(chlorphenyl)-phenylmethane (I), benzophenone (II), o-chlorbenzophenone (III), benzhydrol (IV), and o-(chlorphenyl)-beta-phenylacrolein (V). Two compounds were extracted with chloroform at pH 13--14: unchanged Clofedanol and 1-(o-chlorphenyl)-1-phenyl-3-dimethylaminopropene-1 (VI). N,N-dimethylamino-acetic acid (VII) was also identified in urine. Clofedanol and metabolite IV were present as free compounds, and they were also found after hydrolysis of metabolites VIII and IX with beta-glucuronidase.
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PMID:[Isolation and identification of some metabolites of clofedanol from human urine (author's transl]. 60 21

5-[2-Aminoacetamido)methyl]-1-[p-chloro-2-(o-chlorobenzoyl)phenyl] -N,N-dimethyl-1H-s-triazole-3-carboxamide hydrochloride dihydrate (450191-S) is a ring-opened derivative of 1,4-benzodiazepine, which is activated by desglycylation and subsequent cyclization. After 450191-S administration, rat bile contained three novel conjugates which released active metabolites possessing the 1,4-benzodiazepine structure through beta-glucuronidase hydrolysis. Since the released metabolites have no functional groups to conjugate with glucuronic acid, we speculated that the aglycone might be the ring-opened form of 1,4-benzodiazepine which spontaneously cyclizes after the release of glucuronic acid. This possibility was tested by chemically reducing the ketone group of the ring-opened 1,4-benzodiazepine glucuronate conjugates, which would prevent the spontaneous ring closure reaction after the release of the glucuronic acid moiety. The NaBH4 reduction of the ketone of the benzophenone moiety of the conjugates and subsequent treatment with beta-glucuronidase allowed identification of the reduced aglycones with authentic samples using gas chromatography-mass spectrometry.
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PMID:Identification of novel N-glucuronides in rat bile after administration of 450191-S, a 1H-1,2,4-triazolyl benzophenone derivative. 377 15

The calcium influx inhibitor and cytostatic agent, 5-amino-1-1(4'-chlorobenzoyl-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide (CAI), is in phase I clinical trial for patients with refractory cancer. Additional chromatography peaks were observed during HPLC analysis of patient samples. Identification and characterization of physiological metabolites were undertaken using HPLC techniques developed for their purification from blood, pleural fluid, and urine samples. A hydrophobic metabolite, M1, was purified and functionally characterized. Structural analysis of the purified compound indicated that it is a 3,5-dichloro-4(p-chlorobenzoyl)-benzoic acid. Quantitative analysis of M1 concentration during CAI administration indicated that the rise in M1 concentration lagged behind that of CAI and persisted after CAI was no longer detectable. No clear relationship between CAI or M1 and either toxicity or efficacy was observed. Chromatography of patient blood and urine samples under conditions favoring hydrophilic metabolite detection suggested the presence of a glucuronide compound; this was also indicated by sample treatment with beta-glucuronidase. Attempts at purification did not yield a compound stable for structural analysis. The benzophenone metabolite, M1, was nonfunctional in assays of calcium influx inhibition or proliferation. No pharmacodynamic associations were observed for these metabolites, nor was there pharmacological activity of the M1 as an individual agent. These data suggest that CAI is processed into triazole and benzophenone moieties by phase I metabolism, and these metabolites or the parent compound may be conjugated for excretion by glucuronidation.
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PMID:Identification and characterization of human metabolites of CAI [5-amino-1-1(4'-chlorobenzoyl-3,5-dichlorobenzyl)-1,2,3-triazole- 4-carboxamide). 881 79