title: Characterization of the solution degradation products of etintidine, an H2-receptor antagonist.
abstract: The primary solution degradation products of the antiulcer drug etintidine (1, N"-cyano-N-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]- N'-2-propynylguanidine) were determined to be the guanyl urea 2, the guanidine 3, the amine 4a, and the cyanoamine 4b. These products resulted from nitrile hydrolysis and/or intramolecular cyclization of the guanidino and propargyl groups. The amine 4a was found to be a predominant degradation product in aqueous media of pH 4-7 at 70 +/- 0.2 degrees C.
authors.affiliation: Research Laboratories, Ortho Pharmaceutical Corporation, Raritan, NJ 08869-0602.
authors.forename: A R
authors.initials: AR
authors.lastname: Oyler
authors.forename: R E
authors.initials: RE
authors.lastname: Naldi
authors.forename: S M
authors.initials: SM
authors.lastname: Stefanick
authors.forename: J R
authors.initials: JR
authors.lastname: Lloyd
authors.forename: D A
authors.initials: DA
authors.lastname: Graden
authors.forename: M L
authors.initials: ML
authors.lastname: Cotter
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D004350:Drug Residues / Q000032:analysis; D006635:Histamine H2 Antagonists / Q000032:analysis*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007093:Imidazoles / Q000032:analysis*; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet
chemical_list: D006635:Histamine H2 Antagonists; D007093:Imidazoles; C036616:etintidine