Linked Life Data

978486

Source:http://linkedlifedata.com/resource/pubmed/id/978486

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1976-12-23
pubmed:abstractText
The hydroxylated metabolites of 5,5-diphenylhydantoin (DPH) in dog and human urine, after release by beta-glucuronidase, have been isolated and purified by procedures entailing only solvent partitioning without crystallization or any other procedure that could change the proportions of optical isomers. Dogs produced both the meta- and para-5-hydroxyphenyl-5-phenylhydantoins (m-HPPH and p-HPPH) from DPH, the former in approximately 6 times the amount of the latter. The m-HPPH from dog urine was dextrorotatory and had the properties of a pure optical isomer. The p-HPPH from dog urine was a mixture of optical isomers with approximately a 2:1 preponderance of the levorotatory isomer. When dog urine was heated with acid rather than treated with beta-glucuronidase, the isolated p-HPPH contained a small preponderance of the dextrorotatory isomer, probably owing to production of d-p-HPPH from the dihydrodiol metabolite. No o-HPPH was found in dog urine. When racemic p-HPPH and m-HPPH were administered to dogs, there was little if any preponderance of either optical isomer in the materials isolated from urine. Enzymatically released p-HPPH isolated from urine of human patients receiving DPH was a mixture of optical isomers with approximarely a 10:1 preponderance of the levorotatory isomer. Crystallization of this material readily yields pure l-p-HPPH. Human urine contained only very small amounts of m-HPPH, which was detectable by gas chromatography but insufficient in amount to permit isolation. Hypotheses are discussed that could account for the differences in the metabolism of DPH in man and dog. Small amounts of 2,2-diphenylhydantoic acid were found in urine of dogs but not of human patients receiving DPH.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Oct
pubmed:issn
0022-3565
pubmed:author
pubmed:issnType
Print
pubmed:volume
199
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
82-92
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1976
pubmed:articleTitle
Studies of the metabolism of 5,5-diphenylhydantoin relating principally to the stereoselectivity of the hydroxylation reactions in man and the dog.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.