Corticosteroid usage and binding to arginine: determinants of corticosteroid hypersensitivity

Wilkinson, S. M.; Jones, M.F.

doi:10.1111/j.1365-2133.1996.tb01151.x

Cited by 52 publications

(12 citation statements)

References 22 publications

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“…This suggests that the corticosteroid-glyoxal degradation product is involved in corticosteroid allergy. In vitro, the amount of degradation product, which subsequently reacted with arginine, has been shown to vary between corticosteroids and to be correlated with the frequency of allergic reactions to a steroid (7).…”

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confidence: 99%

Corticosteroid cross‐reactions: an alternative view

Wilkinson

2000

Contact Dermatitis

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An alternative view of corticosteroid cross-reactivity is proposed, based on 2 immune recognition sites on the corticosteroid molecule, 1 influenced by C 6/9 substitution and 1 by C 16/17 substitution. A case report is adduced in support of such a hypothesis.Key words: corticosteroid; cross-reaction; allergic contact dermatitis; tixocortol pivalate; hydrocortisone; budesonide; medicaments; structure-activity relationships. C Munksgaard, 2000. Accepted for publication 9 August 1999Cross-reactions occur between chemicals with similar structures. However, structure is not the only determinant of whether such a reaction will occur (1, 2). On the skin, penetration of the allergen determines whether the immune system will be exposed, and if the substance is a prohapten, its susceptibility to metabolism or degradation determines whether antigen is formed. Metabolism and DegradationThe available evidence suggests that with corticosteroids, the allergen is not the steroid itself but a degradation product. Metabolism and degradation within the skin might therefore be a factor that influences the development of a cross-reaction. It has been suggested that corticosteroids degrade to a reactive corticosteroid-glyoxal that then reacts with arginine ( Fig. 1) to form antigen (3, 4). Clinically, it has been shown that positive patch test reactions to corticosteroid are correlated with patch test reactions to the corresponding corticosteroid-glyoxal (5, 6). This suggests that the corticosteroid-glyoxal degradation product is involved in corticosteroid allergy. In vitro, the amount of degradation product, which subsequently reacted with arginine, has been shown to vary between corticosteroids and to be correlated with the frequency of allergic reactions to a steroid (7).The corticosteroid-glyoxal is formed on the C17 side chain (Fig. 2). Alterations to this chain might therefore affect whether corticosteroid-glyoxal is formed. For practical purposes, the main alterations to this side-chain occur at the C21 position. In the skin, an esterase rapidly splits any ester from the molecule, resulting in a C21 hydroxyl group. In vivo, it has been estimated that within 5 h, 80% in rats, and 50% in dogs, of topically applied hydrocortisone-17-butyrate-21-propionate

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confidence: 99%

Corticosteroid cross‐reactions: an alternative view

Wilkinson

2000

Contact Dermatitis

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“…Recent studies suggest that corticosteroids are not allergens themselves; corticosteroids are degraded to a corticosteroid glyoxal that then reacts with arginine molecules of proteins to form the complete antigen; so, the immune system can recognize the allergen [20, 21]. …”

Section: Discussionmentioning

confidence: 99%

A Case of Cutaneous Delayed-Type Allergy to Oral Dexamethasone and to Betamethasone

et al. 2002

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Corticosteroids are drugs that may cause allergic contact dermatitis, but systemic allergic reactions to these drugs are rare. A 29-year-old man developed a maculopapular rash during an oral therapy with betamethasone. Patch tests demonstrated a delayed-type allergy to dexamethasone, betamethasone and fluocortolone. Oral, intramuscular or topical provocation tests with other corticosteroids – deflazacort, hydrocortisone, methylprednisolone, fluticasone dipropionate, triamcinolone and prednisone – were all negative. This demonstrates that a patient with a systemic allergy to a group of corticosteroids can tolerate those of other groups.

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“…Other protein-binding mechanisms have been described (106). In thiosteroids such as tixocortol pivalate, which has a thioester group at C21, hydrolysis produces tixocortol which binds rapidly to amino acids such as methionine via a disulphur bridge.…”

Section: Protein Bindingmentioning

confidence: 99%

“…It has been shown that steroid glyoxals can bind to every amino acid except proline and hydroxyproline. The arginine reaction, however, is clearly predominant -and also irreversible (106,107). Wilkinson et al (106) showed that CSs with a greater capacity to bind to arginine do have stronger allergenic properties and recently, Berl et al (107) confirmed that steroids selectively react with arginine to form important adducts.…”

Section: Protein Bindingmentioning

confidence: 99%

Allergic hypersensitivity to topical and systemic corticosteroids: a review

Baeck

Marot

Nicolas

et al. 2009

Allergy

101

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Corticosteroids, which are potent anti‐inflammatory and immunomodulator agents used in the treatment of various inflammatory diseases including allergic diseases, can in some cases produce immediate or delayed hypersensitivity reactions. This review summarizes the epidemiological and clinical characteristics of such reactions, including related diagnostic issues. It also presents a detailed analysis of the proposed immunological mechanisms including underlying cross‐reactions.

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Corticosteroid usage and binding to arginine: determinants of corticosteroid hypersensitivity

Cited by 52 publications

References 22 publications

Corticosteroid cross‐reactions: an alternative view

Corticosteroid cross‐reactions: an alternative view

A Case of Cutaneous Delayed-Type Allergy to Oral Dexamethasone and to Betamethasone

Allergic hypersensitivity to topical and systemic corticosteroids: a review

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