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Benzylpenicillenic acid

The interaction of a non-enzymatic degradation product, D-benzylpenicillenic acid (formed by cleavage of the thiazolidine ring of benzylpenicillin in solution see Fig. 10.3B), with sulphydryl or amino groups in tissue proteins, to form hapten-protein conjugates, is also of importance. In particular, the reaction between D-benzylpenicillenic acid and the e-amino group of lysine (a,e-diamino- -caproic acid, NH2(CH2)4.CH(NH2).COOH) residues... [Pg.163]

Fig.3. Dimerization of benzylpenicillin (/ = benzyl) via reactions between the degradation products benzylpenicillenic acid and benzylpenicilloic acid... Fig.3. Dimerization of benzylpenicillin (/ = benzyl) via reactions between the degradation products benzylpenicillenic acid and benzylpenicilloic acid...
Wagner ES, Davis WW, Gorman M (1969) The reaction of benzylpenicillenic acid with thiol-containing compounds. The formation of a possible penicillin antigenic determinant. J Med Chem 12 438-487... [Pg.74]

Reactive derivatives and degradation products benzylpenicillenic acid, benzyl-penicilloic acid in aged penicillin solutions penicillin (especially ampicillin) polymers... [Pg.227]

Butcher BT, Stanfield MK, Stewart GT, Zemelman R (1971) Antibiotic polymers alpha-amino-benzylpenicillin (ampicillin). Mol Cryst Liq Cryst 12 321 Butler TC, Dudley KH, Johnson D (1972) Chemical studies of potential relevance to penicillin hypersensitivity kinetics of formation and disappearance of benzylpenicillenic acid and its derivatives in solutions of benzylpenicillin. J Pharmacol Exp Ther 181 201 Butterly JM, Fishman L (1972) Jarisch-Herxheimer reaction following penicillin therapy in case of symphilitic aortitis. JAMA 148 370... [Pg.467]

Dogliotti M (1975) Tests for penicillin allergy. Med Lett Drugs Ther 17 54 Dry J, Leynadier F, Damecour C, Pradalier A, Herman D (1976) Reaction pseudo-anaphy-lactique a la procaine-penicilline G. Nouv Presse Med 5 1401 Dudley KH, Butler TC, Johnson D (1971) Chemical studies of potential relevance to penicillin hypersensitivity the fate of benzylpenicillenic acid in aqueous buffer solutions. J Pharmacol Exp Ther 179 505... [Pg.469]

Levine BB (1960 c) Formation of D-penicillamine-cysteine mixed disulphide by reaction of D-benzylpenicilloic acide with cysteine Nature 187 940 Levine BB (1961) Studies on the formation of the penicillin antigen. II. Some reactions of D-benzylpenicillenic acid in aqueous solution at pH 7.5. Arch Biochem Biophys 93 50 Levine BB (1962) N(a-D-penicilloyfamines as univalent hapten inhibitors of antibody-de-pendent allergic reactions to penicillin. J Med Chem 5 1025 Levine BB (1963) Studies on the dimensions of the rabbit anti-benzyl penicilloyl antibody combining sites. J Exp Med 117 161... [Pg.474]

Maggs, John Farrell, Catherine S Lane, Andrew V Stachulski, NeU S French, Dean J Naisbitt, Munir Pirmohamed, B. Kevin Park. Direct evidence for the formation of diastereoisomeric benzylpenicUloyl haptens from benzylpenidllin and benzylpenicillenic acid in patients. J Pharmacol Exp Then 2011 338 841-9. Reprinted with permission from Americtm Society for Pharmacology and Experimental Therapeutics... [Pg.135]

Benzylpenicillenic acid, which forms readily from benzylpeniciUin in aqueous solution, is unstable and is thought to be allergenic, particularly in contact skin allergy, after direct reaction with disulfides and cysteine sulfhydryl groups (Fig. 5.6). Immunization of laboratory animals with penicil-lenate-protein and penicilloyl-protein conjugates... [Pg.135]

Benzylpenicillenic acid [38] is not formed in acidic solution (pH < 1) where its rate of formation is pH-independent. [Pg.213]

The presence of copper(II) ion has little effect upon the rate of formation of penicillenic acid from benzylpenicillin. Furthermore, the rates of hydrolysis and aminolysis of benzylpenicillenic acid are retarded in the presence of copper(II) ion. Since the observed rates of hydrolysis and aminolysis of penicillin in the presence of copper(II) ion are at least 10 times faster than the rate of formation of penicillenic acid from penicillin these reactions cannot... [Pg.247]

Unlike other amines, imidazole catalyses the isomerisation of benzylpenicillin to benzylpenicillenic acid [38] (Bundgaard, 1971a,b, 1972, 1976a). The rate law shows that the nucleophilic reaction with imidazole to give the intermediate penicilloylimidazole [65] is general base catalysed by another molecule of imidazole and general acid catalysed by the conjugate acid of imidazole. [Pg.248]

Studies on the chemical aspects of penicillin allergy have shown that the penicilloyl determinant in penicillin allergy can be formed by the reaction of benzylpenicillenic acid with free functional groups in proteins, Benzylpenicillenic acid can react with SH groups of protein to form thio-esters similar to its reaction with amino groups to form amides a. Products obtained in aminolysis and enzymic hydrolysis of cephalosporins... [Pg.158]

In Solvent F, benzylpenicillenic acid and a-methyl-D-benzylpenicilloate had Rf values of 0.38 and 0.53, respectively Time for solvent front to travel 15 cm... [Pg.290]


See other pages where Benzylpenicillenic acid is mentioned: [Pg.104]    [Pg.378]    [Pg.399]    [Pg.262]    [Pg.624]    [Pg.665]    [Pg.404]    [Pg.69]    [Pg.71]    [Pg.427]    [Pg.427]    [Pg.428]    [Pg.430]    [Pg.430]    [Pg.430]    [Pg.197]    [Pg.132]    [Pg.133]    [Pg.135]    [Pg.135]    [Pg.290]    [Pg.294]   
See also in sourсe #XX -- [ Pg.43 , Pg.227 , Pg.427 , Pg.428 , Pg.440 ]

See also in sourсe #XX -- [ Pg.290 , Pg.294 ]




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