Structural determinants of antibiotic allergy

Baldo, Brian A.; Zhao, Zhenjun; Pham, Nghia H.

doi:10.1007/s11882-001-0093-4

Cited by 15 publications

(18 citation statements)

References 48 publications

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“…In keeping with earlier conclusions [1,2], numerous well-known and important antibiotics are rarely implicated in true allergic reactions in humans. For example, the macrolides, which comprise the important antibacterials erythromycin, azithromycin, and clarithromycin, are generally well tolerated.…”

Section: Introductionsupporting

confidence: 85%

“…Adding to the earlier reports on vancomycin allergies [1], Hassaballa et al [3] described such a case. This individual developed anaphylaxis after intravenous (IV) infusion of vancomycin.…”

Section: Vancomycin and Teicoplaninmentioning

confidence: 88%

“…Skin tests with vancomycin proved positive, suggesting that the reaction was at least in part an immediate hypersensitivity response. Another interesting aspect of this case was the subject's tolerance to teicoplanin despite the known crossreactivity between the two glycopeptide antibiotics [1].…”

Section: Vancomycin and Teicoplaninmentioning

confidence: 99%

“…Rifamycin SV is a macrocyclic antibiotic that could act as an allergen [1]; its application has an established track record of immediate allergic reaction. Two reports add to that record.…”

Section: Rifamycin Svmentioning

confidence: 99%

“…Following our earlier review of this field [1], emphasis is on developments from the past 3 to 5 years along with references to earlier studies, if appropriate.…”

Section: Introductionmentioning

confidence: 99%

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Antibiotic allergy: Immunochemical and clinical considerations

Baldo¹,

Zhao²,

Pham³

2008

Curr Allergy Asthma Rep

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Antibiotics are among the most widely and heavily prescribed drugs, but despite this, allergic reactions to most groups of antibiotics are relatively uncommon-especially when compared with the number and frequency of type 1 hypersensitivity responses to the beta-lactams (ie, penicillins, cephalosporins, and, to a lesser extent, carbopenems). Still, there remains a steady flow of reports of allergic reactions to some topically used antibiotics (eg, rifamycin SV and bacitracin). Moreover, aminoglycosides (eg, neomycin and gramicidin) may be implicated more often than previously suspected. Despite advances in our understanding of the structural basis of the allergenicity of beta-lactam antibiotics, the insights have not readily transferred into routine use to improve diagnoses of reactions to individual penicillins and cephalosporins. This remains a challenge in drug allergy, as does the need for further chemical, immunologic, and clinical research on cephalosporin breakdown products and the so-called multiple antibiotic allergy syndrome.

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Section: Introductionsupporting

confidence: 85%

“…Adding to the earlier reports on vancomycin allergies [1], Hassaballa et al [3] described such a case. This individual developed anaphylaxis after intravenous (IV) infusion of vancomycin.…”

Section: Vancomycin and Teicoplaninmentioning

confidence: 88%

Section: Vancomycin and Teicoplaninmentioning

confidence: 99%

“…Rifamycin SV is a macrocyclic antibiotic that could act as an allergen [1]; its application has an established track record of immediate allergic reaction. Two reports add to that record.…”

Section: Rifamycin Svmentioning

confidence: 99%

“…Following our earlier review of this field [1], emphasis is on developments from the past 3 to 5 years along with references to earlier studies, if appropriate.…”

Section: Introductionmentioning

confidence: 99%

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Antibiotic allergy: Immunochemical and clinical considerations

Baldo¹,

Zhao²,

Pham³

2008

Curr Allergy Asthma Rep

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Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects

Zhao

Baldo

Baumgart

et al. 2001

J of Molecular Recognition

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IgE antibodies in the sera of subjects allergic to beta-lactam antibiotics detect a spectrum of specificities ranging from side-chain groups to an entire penicillin or cephalosporin molecule. In addition to such structural heterogeneity of allergenic determinants, IgE antibodies in the sera of different allergic subjects show heterogeneous recognition responses. Detailed immunochemical studies were carried out on the sera of penicillin-allergic subjects that showed selective and unexpected reactions with the frequently prescribed penicillin, amoxicillin. Antibodies from one subject reacted only with the amoxicilloyl determinant while IgE from another subject showed multiple reactivity with penicilloyl and penicillanyl determinants of different penicillins but not with the amoxicilloyl determinant. Quantitative hapten inhibition studies revealed that the combining sites of the former antibodies were complementary to amoxicillin in a form that permits binding to the hydroxyaminobenzyl side-chain and the thiazolidine ring carboxyl. These conditions are satisfied with the drug in the '-oyl' but not in the '-anyl' form which involves linkage through the 2-carboxyl of the thiazolidine ring. With the second serum, adsorption studies showed that the wide-ranging reactivity of IgE was due to a single population of antibodies that detected a common specificity on the different penicillins. Combining site studies revealed clear recognition of the benzyl portion of the side-chain of benzylpenicilloyl, benzylpenicillanyl, ampicilloyl, ampicillanyl and amoxicillanyl determinants when free antibody access to the side-chain was possible but little or no recognition of the ring hydroxyl of amoxicillin. Such uninhibited access may not occur, however, when amoxicillin is conjugated in the '-oyl' form since opening the beta-lactam ring allows increased flexibility and rotation of the molecule and the possibility of close association of the hydroxyaminobenzyl side-chain of amoxicillin with the linked peptide carrier. In such close steric association, H-bonding involving the ring hydroxyl and amino acids of the carrier may prevent antibody access to the side-chain region of the amoxicilloyl determinant.

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Other Antimicrobial Drugs

Baldo¹,

Pham²

2020

Drug Allergy

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Structural determinants of antibiotic allergy

Cited by 15 publications

References 48 publications

Antibiotic allergy: Immunochemical and clinical considerations

Antibiotic allergy: Immunochemical and clinical considerations

Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects

Other Antimicrobial Drugs

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