The Role of Penicilloylated Protein Impurities, Penicillin Polymers and Dimers in Penicillin Allergy (Part 2 of 2)

Weck, A.L. de; Schneider, C.H.; Gutersohn, J.

doi:10.1159/000316032

Cited by 5 publications

(7 citation statements)

References 13 publications

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“…In both these studies the specificity of the reactions observed was demonstrated to be predominantly penicilloyl as verified by hapten inhibition experiments or immunosorbent experiments. Other investigators (12,14,17,(44)(45)(46) have similarly demonstrated the antigenicity of polymeric substances derived from various penicillins.…”

Section: Immunological Efects Of Polymersmentioning

confidence: 88%

“…A similar observation has also been made by de Weck er al. (14) in the case of a 10% w/v penicillin solution. This reduction in polymerization through keeping the pH in the range 7-7.5 is in accordance with the postulated mechanism for the polymerization since penicillenic acid is formed only very slowly at neutral pH.…”

Section: Fig 2 Dimerizatron Of Benzylpenicillin (R=benzyl) Via Reacmentioning

confidence: 99%

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Pharmaceutical Aspects of Penicillin Allergy: Polymerization of Penicillins and Reactions With Carbohydrates

Bundgaard

1980

J Clin Pharm Ther

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In this paper recent experimental results of some pharmaceutical aspects of penicillin allergy are reviewed. Among products assumed to be involved in the elicitation of allergic reactions to penicillin preparations are penicillin polymers and penicilloyl‐carbohydrate conjugates. The polymers are formed by reaction of penicillins with themselves or with their degradation products, whereas the carbohydrate esters arise from reaction of penicillins with carbohydrates used as excipients in various penicillin preparations. A survey and discussion of available data on the rate and mechanism of formation, chemical structure and immunological effects of these products are given along with considerations of possible approaches to depress or prevent the formation of the products by proper formulation and storage of penicillin preparations.

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Section: Immunological Efects Of Polymersmentioning

confidence: 88%

Section: Fig 2 Dimerizatron Of Benzylpenicillin (R=benzyl) Via Reacmentioning

confidence: 99%

Pharmaceutical Aspects of Penicillin Allergy: Polymerization of Penicillins and Reactions With Carbohydrates

Bundgaard

1980

J Clin Pharm Ther

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“…Their immunogenicity is thus related to their ability to bind to proteins. Examples of such chemically reactive drugs are P-lactams and sulfonamides, two of the most frequently sensitizing drugs, which are reactive either per se (p-lactams) or after drug metabolism (sulfonamides) (17)(18)(19)(20)(21)(22).…”

Section: Chemically Reactive and Nonreactive Drugsmentioning

confidence: 99%

“…Early studies showed that the p-lactam ring spontaneously opens under physiologic conditions so that its carbonyl moiety can form an amide linkage, mainly to the e-amino groups of proteins. Thereby is formed the penicilloyl group, which can act as an immunogen (19)(20)(21). Other conjugations occur by degradation of penicillin to penicillenic or penicilloic acid, which forms disulfide bonds with sulfidryl groups of cysteine (minor antigenic determinants) (23).…”

Section: Chemically Reactive and Nonreactive Drugsmentioning

confidence: 99%

Role of T cells in drug allergies

Pichler

Schnyder

Zanni

et al. 1998

Allergy

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“…In 1967, Batchelor et al (2) and Stewart (17) postulated that penicilloylated protein impurities and penicillin polymers, which were isolated from commercially available benzylpenicillin preparation, may be the possible antigens in penicillin allergy. However, several studies have failed to show that the benzylpenicillin preparations gave positive PCA reactions in guinea pigs sensitized cutaneously with either anti-BPO y,-antibodies or anti-BPO y2-antibodies, and have also reported that the preparations could not evoke systemic anaphylactic reactions in sensitized animals (5,7,13).…”

Section: Correlation Between the Severity Of Systemic Anaphylactic Rementioning

confidence: 99%

Antigenicity of Semisynthetic Penicillin Preparations to Evoke Systemic Anaphylactic Reactions in Animal Models

Koizumi

Suzuki

Fukuba

et al. 1980

Allergy

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Four commercially available penicillin preparations (benzylpenicillin, aminobenzylpenicillin, carbenicillin and sulbenicillin) and two kinds of the new semisynthetic penicillin preparations (mezlocillin and piperacillin) evoked systemic anaphylactic reactions in guinea pigs immunized with one of the following penicillin-Ascaris extract (As) conjugates in aluminum hydroxide gel (alum), i.e., benzylpenicilloyl (BPO)-As, aminobenzylpenicilloyl (ABPO)-As, carbenicilloyl (CBPO)-As, sulbenicilloyl (SBPO)-As, mezlocillin-As conjugate (MEZ-As) and piperacillin-As conjugate (PIP-As). The tracheal chains prepared from the tracheas of the guinea pigs immunized with BPO-As, MEZ-As, or PIP-As revealed anaphylactic contractions in vitro on addition of benzylpenicillin, mezlocillin, or piperacillin preparations. These results indicated that the semisynthetic penicillin preparations as well as benzylpenicillin preparation have enough antigenicity to evoke systemic anaphylactic reactions in guinea pigs immunized with penicillin-As conjugate. Such guinea pigs seem to be suitable animals for investigations of penicillin allergy.

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The Role of Penicilloylated Protein Impurities, Penicillin Polymers and Dimers in Penicillin Allergy (Part 2 of 2)

Cited by 5 publications

References 13 publications

Pharmaceutical Aspects of Penicillin Allergy: Polymerization of Penicillins and Reactions With Carbohydrates

Pharmaceutical Aspects of Penicillin Allergy: Polymerization of Penicillins and Reactions With Carbohydrates

Role of T cells in drug allergies

Antigenicity of Semisynthetic Penicillin Preparations to Evoke Systemic Anaphylactic Reactions in Animal Models

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