Biomaterial Database

Aromatic hydroxylation of beta-adrenergic antagonists. Formation of 4'- and 5'-hydroxy-1-(isopropylamino)-3-[2'-allyloxy)phenoxy]-2-propanol from oxprenolol. 1979

W L Nelson, and T R Burke

The metabolic aromatic hydroxylation of oxprenolol [1-(isopropylamino)-3-[2'-(allyloxy)phenoxy]-2-propanol] in rats was examined. Synthesis of the isomeric ring methoxyoxprenolols (3b-6b) was accomplished from the isomeric methoxysalicylaldehydes by O-allylation, followed by Baeyer-Villiger oxidation. The propanolamine side chain was elaborated by O-alkylation of the Bayer-Villiger product with epichlorohydrin and subsequent oxirane opening with isopropylamine. Gas chromatography-mass spectra of the trifluoroacetyl derivatives of these standards was compared with urinary metabolites obtained from the rat, after methylation with diazomethane and derivatization with trifluoroacetic anhydride. Both 4'- and 5'-hydroxyoxprenolol (4a and 5a) were present in an approximate 4:1 ratio. No 3'- or 6'-hydroxyoxprenolol (3a and 6a) was detected. The metabolites obtained from a human urine treated in the same manner gave similar results with both 4a and 5a present.

UI	MeSH Term	Description	Entries
D008297	Male		Males
D008745	Methylation	Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	Methylations
D010096	Oxprenolol	A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	Coretal,Koretal,Oxprenolol Hydrochloride,Slow Trasicor,Tevacor,Trasicor,Hydrochloride, Oxprenolol,Trasicor, Slow
D002849	Chromatography, Gas	Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix.	Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D006801	Humans	Members of the species Homo sapiens.	Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D006900	Hydroxylation	Placing of a hydroxyl group on a compound in a position where one did not exist before. (Stedman, 26th ed)	Hydroxylations
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D001711	Biotransformation	The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.
D013058	Mass Spectrometry	An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers.	Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D051381	Rats	The common name for the genus Rattus.	Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus