Cephalosporin-Allergic Patients - Subsequent Use of Cephalosporins and Related Antibiotics

9/21/2016 Cephalosporin-allergic patients: Subsequent use of cephalosporins and related antibiotics
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Cephalosporinallergic patients: Subsequent use of cephalosporins and related antibiotics
Author Section Editor Deputy Editor

Antonino Romano, MD N Franklin Adkinson, Jr, MD Anna M Feldweg, MD
All topics are updated as new evidence becomes available and our peer review process is complete.
Literature review current through: Aug 2016. | This topic last updated: Oct 16, 2014.
INTRODUCTION — Cephalosporins are commonlyused antibiotics that can cause a variety of
hypersensitivity reactions. The reactions can be broadly classified as follows:
● Immediate reactions are reactions that develop within one hour of administration. These are usually
type I, immunoglobulin E (IgE)mediated reactions and are characterized by urticaria, angioedema,
bronchospasm, and/or hypotension (table 1).
● Nonimmediate reactions are reactions that develop >1 hour of administration, often after several hours
or days. Common delayed reactions include maculopapular rashes and urticarial eruptions. Rare types
of delayed reactions include serum sicknesslike reactions, drug fever, and druginduced
hypersensitivity syndrome.
Patients with past reactions to a specific cephalosporin may require subsequent treatment with a different
cephalosporin or a related antibiotic, such as a penicillin, carbapenem, or monobactam. Approaches to
these different clinical scenarios will be presented here. The clinical manifestations, pathogenesis, and
diagnosis of different types of cephalosporinhypersensitivity reactions are reviewed separately. (See
"Cephalosporin allergy: Clinical manifestations and diagnosis".)
PAST IMMEDIATE REACTIONS — Patients with past immediate reactions to cephalosporins who require
subsequent use of other cephalosporins or penicillins should be evaluated by an allergy specialist. The
purpose of this evaluation, which usually involves skin testing, is to determine what other drugs may be
safely administered to that patient. Most patients will be able to tolerate other cephalosporins and/or
penicillins.
Cross reactivity among cephalosporins and between cephalosporins and penicillins may arise from the
following:
● Sensitization to structurally similar R1 side chain groups (most common) or R2 side chain groups
(figure 1) [111]
● Sensitization to the core betalactam ring, contained in both penicillins and cephalosporins, or
metabolites of this ring
Sensitization to the R1 side chain group of cephalosporins is believed to be important in determining cross
reactivity among cephalosporins, as well as among cephalosporins and amoxicillin and ampicillin (which
share side chains with certain cephalosporins) (figure 2).
Because of the different possible sensitization patterns, we suggest evaluating patients with immediate
cephalosporin reactions with prick/puncture and intradermal skin testing to all of the following:
● The classic penicillin reagents (penicilloylpolylysine [PPL], the minor determinant mixture [MDM], and
benzylpenicillin). (See "Penicillin skin testing", section on 'Skin testing reagents and concentrations'.)
● Ampicillin and amoxicillin (to detect patients who are sensitized to side chain groups that are shared by
these aminopenicillins and some cephalosporins).
● The cephalosporin that caused the past reaction.
● One or more alternative cephalosporins with different R groups from the culprit drug, which the patient
could potentially receive instead.
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Skin testing to cephalosporins and to penicillins is described in detail separately. (See "Cephalosporin
allergy: Clinical manifestations and diagnosis", section on 'Indications for skin testing' and "Penicillin skin
testing" and "Penicillin allergy: Immediate reactions".)
Use of other cephalosporins — When approaching a patient with a history of an immediate cephalosporin
reaction, the clinician should be mindful of the following:
● Similarities among side chain groups alone cannot be relied upon to predict cross sensitivity accurately
[14,7,9]. Rather, these similarities are best used to select structurally different cephalosporins from the
one that caused the initial reaction to which the patient is less likely to react. The evaluation must still
include skin testing, and, in case of negative results, graded challenge to determine if the selected
cephalosporin can be safely administered. Graded challenges typically involve two or three steps. The
starting dose is usually 1/100 or 1/10 of the full dose. Tenfold increasing doses are administered every
30 to 60 minutes until the full therapeutic dose is reached. Graded challenges are discussed in more
detail elsewhere. (See "Penicillin allergy: Immediate reactions".)
We suggest selecting for evaluation a cephalosporin that has a different side chain, especially in the R1
position, from the cephalosporin that caused the past reaction. However, a similar side chain should
not absolutely exclude a drug from consideration if it is the most appropriate drug for the clinical
situation.
● The results of skin tests (or in vitro tests, where available) for cephalosporin allergy may not translate
into clinical cross reactivity. For ethical reasons, very few studies have confirmed the accuracy of
positive testing results by challenging patients with a drug to which they tested positive. Therefore, skin
tests need to be followed by graded challenge to determine if the selected cephalosporin is tolerated.
With the above caveats in mind, there are studies demonstrating the utility of considering side chain groups
when selecting an alternative cephalosporin. As examples, ceftriaxone, cefotaxime, cefepime, and
cefuroxime have similar or identical R1 side chains (containing a methoxyimino group) and cross reactivity
among these drugs is regularly reported (figure 3) [9]. Ceftazidime has a R1 side chain that is slightly
different from ceftriaxone, cefotaxime, cefepime, and cefuroxime. The ceftazidime R1 side chain has an
alkoxyimino group that has greater steric hindrance than the methoxyimino moiety, and so would not be
expected to be recognized by the same immunoglobulin E (IgE) molecules [5]. Consistent with this, one
study found a significant degree of cross reactivity between cefotaxime and ceftriaxone (odds ratio [OR] =
7.0, 95% CI 224), but not between these two cephalosporins and ceftazidime [9]. However, in some studies
by the author's group, there were subjects who had experienced immediate hypersensitivity reactions to
ceftazidime, as well as to cefotaxime and/or ceftriaxone in separate episodes and displayed positive results
in allergy tests with the responsible compounds [2,3]. Therefore, cross reactivity among these
cephalosporins seems to be possible as well.
The following algorithm depicts an approach to identifying a safe alternative cephalosporin in a patient with a
past immediate cephalosporin reaction (algorithm 1):
● The clinician should choose one or more alternative cephalosporins that have different side chains,
especially in the R1 position, from the responsible compounds (figure 2 and figure 3).
● Skin testing should be performed to the desired cephalosporin. (See "Cephalosporin allergy: Clinical
manifestations and diagnosis", section on 'Indications for skin testing'.)
● If the results are positive, then the patient should be assumed to be allergic to the desired
cephalosporin and it should only be administered using a desensitization protocol. (See "Rapid drug
desensitization for immediate hypersensitivity reactions".)
● If the results are negative, then the desired cephalosporin can be administered by graded challenge to
confirm that the drug is tolerated.
Use of the same cephalosporin that caused a previous reaction — Rarely, a patient requires the same
cephalosporin to which there is evidence of IgEmediated allergy. A formal desensitization protocol should
be performed in this situation. The procedure described for penicillin desensitization would be appropriate.
(See "Rapid drug desensitization for immediate hypersensitivity reactions".)
Use of penicillins — Most patients with immediate reactions to cephalosporins and no history of reacting to
penicillins will tolerate penicillins. However, there are patients who react to both groups of drugs and there
are at least three allergenic determinants that are shared by penicillins and cephalosporins that may be
responsible for this cross reactivity:
● Side chain groups – Side chain groups may be the most common source of cross reactivity between
cephalosporins and penicillins. In one study, patients with past reactions to cephalosporins with similar
or identical side chains with penicillins demonstrated a threefold increased incidence of positive results
in allergy tests with that penicillin [11]. Amoxicillin has the same side chain as cefadroxil, cefprozil, and
cefatrizine. Ampicillin has the same side chain as cefaclor, cephalexin, cephradine, cephaloglycin, and
loracarbef (figure 2).
● Small moieties – Small moieties shared by cephalosporins and penicillins can also be allergenically
important. In one study, a population of IgE antibodies recognizing a methylene group present in both
cephalothin and benzylpenicillin was identified in patient sera [10]. Positive skin tests to both
benzylpenicillin and cephalothin have been observed in such patients.
● Betalactam ring – A small percentage of patients with primary cephalosporin reactions may be
sensitized to the betalactam core that is common to both cephalosporins and penicillins (figure 1) [3].
The pathophysiology of penicillin allergy and the role of the betalactam ring are reviewed in greater
detail elsewhere. (See "Penicillin allergy: Immediate reactions", section on 'Pathogenesis'.)
Therefore, if a patient reacted to a cephalosporin in the past and now requires a penicillin, then penicillin skin
testing is indicated to guide management as follows (algorithm 2):
● Negative results on penicillin skin testing indicate that the patient's reaction to the cephalosporin was
probably due to a unique cephalosporin determinant. Therefore, the patient is not at increased risk for
reacting to a penicillin, provided that penicillin does not share a side chain with the cephalosporin that
caused the initial reaction (figure 2).
● Positive results on penicillin skin testing indicate that the patient may be reactive to the betalactam
core, provided that the penicillin and cephalosporin in question do not share similar side chains. The
patient may be treated with a non betalactam antibiotic or desensitized to the desired penicillin. (See
"Penicillin allergy: Immediate reactions", section on 'Desensitization'.)
If penicillin skin testing is not available, we would suggest selecting a penicillin that does NOT have a side
chain similar to that on the culprit cephalosporin, and skin testing with that penicillin (in its native form)
(figure 2). If negative, we suggest performing a graded challenge to the penicillin.
Use of carbapenems and monobactams — Patients with immediate cephalosporin allergy usually tolerate
carbapenems (eg, imipenem/cilastatin, meropenem, ertapenem, and doripenem) and monobactams (ie,
aztreonam) [11,12]. In the largest study available, 98 patients with convincing histories of immediate
cephalosporin reactions and positive skin tests to the culprit cephalosporin underwent allergy evaluation and
graded challenge with several related medications. Overall, fewer than 5 percent had positive skin tests to
carbapenems or monobactams [11]. For ethical reasons, patients with positive skin tests were not
challenged to determine if the positive results were true:
● Carbapenems share a common fourmembered betalactam ring with cephalosporins (and penicillins)
and hence the potential for allergic cross reactivity (figure 4). However, clinical cross reactivity with
cephalosporins appears to be rare. In the study mentioned above, only 1 of 98 subjects was skintest
positive to both cephalosporins and carbapenems (both meropenem and imipenem/cilastatin), and this
patient also tested positive to penicillin reagents and aztreonam. Therefore, his IgE antibodies were
probably directed against the betalactam ring, which is shared by all betalactams [11]. In the 97
subjects with negative skin tests to carbapenems, graded challenges were performed with meropenem
and imipenem/cilastatin and were well tolerated by 96 patients. The one remaining subject developed a
mild urticarial eruption 30 minutes after the full dose of imipenem/cilastatin.
The author's recommended approach to patients with a history of an immediate reaction to a
cephalosporin, who now require a carbapenem, is to obtain an allergy consultation and perform skin
testing with the carbapenem in question. The concentrations used in the study above were meropenem
at 1 mg/mL and imipenem/cilastatin at 0.5 mg/mL for each component [11].
• If skin tests are negative, the carbapenem can be given by graded challenge (eg, 1/100, then 1/10,
then full dose, each separated by 30 to 60 minutes of observation).
• If skin tests are positive, the carbapenem should be given only if there is no alternative drug and
then, using a desensitization protocol. (See "Rapid drug desensitization for immediate
hypersensitivity reactions".)
● Aztreonam is the only monobactam clinically available. Although it contains a monocyclic betalactam
core, it does not pose a risk to patients allergic to penicillin. However, aztreonam shares a side chain
structure with ceftazidime, and clinical cross reactivity has been reported between aztreonam and
ceftazidime [13,14]. Despite the similarity in side chain groups, not all ceftazidimeallergic patients react
to aztreonam [11,15], and not all aztreonamallergic patients react to ceftazidime [16]. Therefore, we
suggest that patients who experienced immediate reactions to ceftazidime in the past and now require
aztreonam be skin tested to aztreonam (2 mg/mL).
• If aztreonam skin test results are negative, the patient can receive the drug using a graded
challenge.
• If aztreonam skin tests to aztreonam are positive and the patient has a particular need for this
drug, then it should be administered using a rapid desensitization protocol. (See "Rapid drug
desensitization for immediate hypersensitivity reactions".)
• If an allergy evaluation is not possible, then we suggest informing the patient that the risk of
reacting to aztreonam is estimated at less than 5 percent [11] and then performing a graded
challenge.
PAST NONIMMEDIATE REACTIONS — Management options for patients with past nonimmediate reactions
to cephalosporins depend upon the specific type of reaction that occurred. Structural similarities among
drugs might predict the recurrence of some nonimmediate reactions. Cross reactivity between
aminopenicillins (eg, ampicillin, amoxicillin, and bacampicillin) and aminocephalosporins, like cephalexin has
been reported [17].
Past maculopapular rash — The occurrence of this common type of nonimmediate reaction does not
necessitate future avoidance of the culpritsuspected medication in the majority of patients [18]. These
reactions are not accompanied by fever, blistering of the skin or mucous membranes, or systemic
symptoms. The presence of fever, mucosal involvement, or systemic symptoms should be interpreted as a
more severe type of drug reaction and the culprit cephalosporin should not be given again.
It is the author's approach to perform delayedreading intradermal tests, and in patients with negative
results, challenges with the suspected drugs. This evaluation is described separately. (See "Cephalosporin
allergy: Clinical manifestations and diagnosis", section on 'Evaluation of nonimmediate reactions'.)
● In a study from the author's center of 105 children with delayed reactions to cephalosporins, all had
negative reactions to patch testing and delayed readings of intradermal testing, and just one had
positive skin test results for IgEmediated penicillin allergy [19]. The 104 children with negative tests
were offered challenge with the cephalosporin to which they initially reacted. Of the 95 patients who
accepted challenge, all tolerated the drug. One patient developed hives to a suspension of the drug,
but tolerated it in capsules, indicating that the reaction was due to an excipient [19]. In another study of
105 adults with nonimmediate reactions, only five patients demonstrated positive responses to
delayedreading intradermal tests with the responsible cephalosporins, of whom three were also patch
test positive [17].
● In a study by a different group, 12 (4.1 percent) of 290 patients with cutaneous adverse reactions to
cephalosporins displayed positive responses to patch tests with the responsible cephalosporins [20].
Only 1 of the 75 patients with cutaneous eruptions associated with cephalosporins and negative results
in patch tests reacted to the provocation tests with the suspected cephalosporins (cefadroxil or
cephalexin).
In the United States, the most common approach is simply to use a different cephalosporin in the future. If
the culprit cephalosporin is specifically required, it can be administered using a graded challenge.
Delayedonset urticaria/angioedema — This type of nonimmediate reaction to cephalosporins is managed
similarly to maculopapular rash, although immediatetype skin testing should be performed to exclude IgE
sensitization. The evaluation of delayedonset urticaria/angioedema is discussed elsewhere. (See
"Cephalosporin allergy: Clinical manifestations and diagnosis", section on 'Evaluation of nonimmediate
reactions'.)
Past serum sickness — Cefaclor is the cephalosporin most commonly implicated in serum sicknesslike
reactions, particularly in children. These patients can receive other cephalosporins normally in the future,
including the structurally similar agent loracarbef [21].
USE OF CEPHALOSPORINS IN PATIENTS ALLERGIC TO PENICILLINS — Among patients reporting a
penicillin allergy, 1 to 11 percent can be expected to react to a cephalosporin if no objective diagnostic
testing is performed. Aspects of the history, including the clinical features and severity of the penicillin
reaction and the time elapsed since the reaction, are important in estimating an individual's risk. An
approach to treating penicillinallergic patients with cephalosporins, with and without additional testing, is
reviewed in detail separately. (See "Penicillinallergic patients: Use of cephalosporins, carbapenems, and
monobactams", section on 'Cephalosporins'.)
SUMMARY AND RECOMMENDATIONS
Immediate reactions — Immediate reactions are reactions that develop within one hour of administration.
These are usually type I, immunoglobulin E (IgE)mediated reactions and are characterized by urticaria,
angioedema, bronchospasm, and/or hypotension (table 1). (See "Cephalosporin allergy: Clinical
manifestations and diagnosis", section on 'Immediate reactions'.)
● Patients with past immediate reactions to a cephalosporin can often be safely treated with other beta
lactam drugs, including structurally dissimilar cephalosporins, penicillins, carbapenems, and
monobactams. However, this requires an understanding of what is known about cross reactivity
patterns among cephalosporins and related drugs. (See 'Introduction' above.)
● Cross reactivity among cephalosporins and between cephalosporins and penicillins commonly arises
from structural similarities in side chain groups or rarely from sensitization to the core betalactam ring
(present both penicillins and cephalosporins) or metabolites of this ring (figure 1). (See 'Past immediate
reactions' above.)
● Patients with past immediate reactions to cephalosporins who require subsequent use of related
antibiotics should be evaluated by an allergy specialist when possible. The purpose of this evaluation is
to determine what other drugs may be safely administered to that patient. An algorithm depicts the
approach to identifying a safe alternative cephalosporin in a patient with a past immediate
cephalosporin reaction (algorithm 1). (See 'Use of other cephalosporins' above.)
● Most patients with immediate reactions to cephalosporins and no history of reacting to penicillins will
tolerate penicillins. If a patient reacted to a cephalosporin in the past and now requires a penicillin, then
penicillin skin testing is indicated to guide management as shown (algorithm 2). (See 'Use of penicillins'
above.)
● Patients with immediate cephalosporin allergy usually tolerate carbapenems (eg, imipenem/cilastatin,
meropenem, ertapenem, and doripenem). An approach to evaluating such patients, which involves
carbapenem skin testing, is described. (See 'Use of carbapenems and monobactams' above.)
● Aztreonam is the only monobactam available for clinical use. There is no evidence of immunologic
cross reactivity between the core cephalosporin structure and monobactams, so most cephalosporin
allergic patients may receive aztreonam normally. An exception is the patient with a past immediate
reaction to ceftazidime, because aztreonam and ceftazidime share an identical side chain, and cross
reactivity between the two drugs is reported. An approach to evaluating such patients, which involves
aztreonam skin testing, is described. (See 'Use of carbapenems and monobactams' above.)
Nonimmediate reactions — Nonimmediate reactions are reactions that develop >1 hour after
administration, and include uncomplicated maculopapular rashes, delayedonset urticaria/angioedema, and
serum sickness. These reactions are not accompanied by fever, blistering of the skin or mucous
membranes, or systemic symptoms. The presence of fever, mucosal involvement, or systemic symptoms
should be interpreted as a more severe type of drug reaction and the culprit cephalosporin should not be
given again. (See 'Past nonimmediate reactions' above.)
● Structural similarities among drugs might predict the recurrence of nonimmediate reactions. Cross
reactivity between aminopenicillins and aminocephalosporins has been described. Management
options depend upon the type of reaction that occurred. Patients can safely receive other
cephalosporins, and in many cases, the same cephalosporin again in the future. (See 'Past
nonimmediate reactions' above.)
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REFERENCES
1. Romano A, Quaratino D, AimoneGastin I, et al. Cephalosporin allergy: Characterization of unique and
crossreaction cephalosporin antigens. Int J Immunopathol Pharmacol 1997; 10:Suppl 2:187.
2. Romano A, Mayorga C, Torres MJ, et al. Immediate allergic reactions to cephalosporins: cross
reactivity and selective responses. J Allergy Clin Immunol 2000; 106:1177.
3. Romano A, GuéantRodriguez RM, Viola M, et al. Diagnosing immediate reactions to cephalosporins.
Clin Exp Allergy 2005; 35:1234.
4. Antunez C, BlancaLopez N, Torres MJ, et al. Immediate allergic reactions to cephalosporins:
evaluation of crossreactivity with a panel of penicillins and cephalosporins. J Allergy Clin Immunol
2006; 117:404.
5. Hasdenteufel F, Luyasu S, Renaudin JM, et al. Anaphylactic shock associated with cefuroxime axetil:
structureactivity relationships. Ann Pharmacother 2007; 41:1069.
6. Varela Losada S, González de la Cuesta C, AlvarezEire MG, González González C. Immediatetype
allergic reaction to cefuroxime: crossreactivity with other cephalosporins, and good tolerance to
ceftazidime. J Investig Allergol Clin Immunol 2009; 19:164.
7. Nagakura N, Shimizu T, Masuzawa T, Yanagihara Y. Anticephalexin monoclonal antibodies and their
crossreactivities to cephems and penams. Int Arch Allergy Appl Immunol 1990; 93:126.
8. PerezInestrosa E, Suau R, Montañez MI, et al. Cephalosporin chemical reactivity and its
immunological implications. Curr Opin Allergy Clin Immunol 2005; 5:323.
9. Guéant JL, GuéantRodriguez RM, Viola M, et al. IgEmediated hypersensitivity to cephalosporins.
Curr Pharm Des 2006; 12:3335.
10. Zhao Z, Baldo BA, Rimmer J. betaLactam allergenic determinants: fine structural recognition of a
crossreacting determinant on benzylpenicillin and cephalothin. Clin Exp Allergy 2002; 32:1644.
11. Romano A, Gaeta F, Valluzzi RL, et al. IgEmediated hypersensitivity to cephalosporins: cross
reactivity and tolerability of penicillins, monobactams, and carbapenems. J Allergy Clin Immunol 2010;
126:994.
12. Kula B, Djordjevic G, Robinson JL. A systematic review: can one prescribe carbapenems to patients
with IgEmediated allergy to penicillins or cephalosporins? Clin Infect Dis 2014; 59:1113.
13. Pérez Pimiento A, Gómez Martínez M, Mínguez Mena A, et al. Aztreonam and ceftazidime: evidence
of in vivo cross allergenicity. Allergy 1998; 53:624.
14. Adkinson NF Jr. Immunogenicity and crossallergenicity of aztreonam. Am J Med 1990; 88:12S.
15. Moss RB. Sensitization to aztreonam and crossreactivity with other betalactam antibiotics in highrisk
patients with cystic fibrosis. J Allergy Clin Immunol 1991; 87:78.
16. Iglesias Cadarso A, Sáez Jiménez SA, Vidal Pan C, Rodriguez Mosquera M. Aztreonaminduced
anaphylaxis. Lancet 1990; 336:746.
17. Romano A, Gaeta F, Valluzzi RL, et al. Diagnosing nonimmediate reactions to cephalosporins. J
Allergy Clin Immunol 2012; 129:1166.
18. Romano A, Blanca M, Torres MJ, et al. Diagnosis of nonimmediate reactions to betalactam
antibiotics. Allergy 2004; 59:1153.
19. Romano A, Gaeta F, Valluzzi RL, et al. Diagnosing hypersensitivity reactions to cephalosporins in
children. Pediatrics 2008; 122:521.
20. Lammintausta K, KortekangasSavolainen O. The usefulness of skin tests to prove drug
hypersensitivity. Br J Dermatol 2005; 152:968.
21. Kearns GL, Wheeler JG, Rieder MJ, Reid J. Serum sicknesslike reaction to cefaclor: lack of in vitro
crossreactivity with loracarbef. Clin Pharmacol Ther 1998; 63:686.
Topic 13536 Version 9.0
GRAPHICS
Symptoms and signs of anaphylaxis
Skin
Feeling of warmth, flushing (erythema), itching, urticaria, angioedema, and "hair standing
on end" (pilor erection)
Oral
Itching or tingling of lips, tongue, or palate
Edema of lips, tongue, uvula, metallic taste
Respiratory
Nose Itching, congestion, rhinorrhea, and sneezing
Laryngeal Itching and "tightness" in the throat, dysphonia, hoarseness, stridor
Lower airways Shortness of breath (dyspnea), chest tightness, cough, wheezing, and
cyanosis
Gastrointestinal
Nausea, abdominal pain, vomiting, diarrhea, and dysphagia (difficulty swallowing)
Cardiovascular
Feeling of faintness or dizziness; syncope, altered mental status, chest pain, palpitations,
tachycardia, bradycardia or other dysrhythmia, hypotension, tunnel vision, difficulty
hearing, urinary or fecal incontinence, and cardiac arrest
Neurologic
Anxiety, apprehension, sense of impending doom, seizures, headache and confusion;
young children may have sudden behavioral changes (cling, cry, become irritable, cease to
play)
Ocular
Periorbital itching, erythema and edema, tearing, and conjunctival erythema
Other
Uterine cramps in women and girls
Original figure modified for this publication. Simons FER. Anaphylaxis. J Allergy Clin Immunol 2010;
125:S161. Table used with the permission of Elsevier Inc. All rights reserved.
Graphic 66333 Version 15.0
Comparison of cephalosporin and penicillin
structures
Cephalosporins and penicillins share a fourmembered betalactam ring.
Cephalosporins have a sixmembered dihydrothiazine ring, while
penicillins have a fivemembered thiazolidine ring. The R1, and to a
lesser extent, the R2 side groups on cephalosporins are important in
generating allergenic epitopes.
R: side chain group.
Courtesy of Antonino Romano, MD.
Side chains shared by penicillins and cephalosporins
Some penicillins and cephalosporins share identical or similar side chain groups, leading to
possible clinical cross reactivity. Ampicillin has the same side chain in the R1 position as
cephalexin and cefaclor, as well as (not shown) cephradine, cephaloglycin, and loracarbef.
Amoxicillin has the same side chain as cefadroxil, cefatrizine, and (not shown) cefprozil.
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Side chains and side chain groups that are shared among
cephalosporins
Several cephalosporins share the same moeities at the R1 side chain position (shown in the
boxes). The more similar the R1 side chains, the more likely it is that a patient allergic to one will
also react to another. Specifically, ceftriaxone, cefuroxime, cefotaxime, and cefepime each have a
methoxymino group (circled) within the R1 side chain and cross reactivity is observed in patients
allergic to these agents. In contrast, ceftazidime has a different structure in the R1 position, and
cross reactivity with the other agents is not frequently observed.
Administration of a cephalosporin to a patient with
a history of an immediate allergic reaction to
another cephalosporin
Adapted with permission from: Figure 1 in Ann Allergy Asthma Immunol
1999; 83: Suppl. Copyright © 1999 American College of Allergy, Asthma and
Immunology.
Administration of penicillin to a patient with a
history of an immediate allergic reaction to a
cephalosporin
Adapted with permission from: Figure 1 in Ann Allergy Asthma Immunol
1999; 83: Suppl. Copyright ©1999 American College of Allergy, Asthma and
Immunology.
Structure of penicillins and related betalactam
drugs
R: side chain group.
Contributor Disclosures
Antonino Romano, MD Consultant/Advisory Boards: Diater SA [Reagents for diagnosis of penicillin allergy
(DAP)]. N Franklin Adkinson, Jr, MD Consultant/Advisory Boards: Regado; Merck; Boehringer Ingelheim
[Hypersensitivity reactions and anaphylaxis in drugs under development (Fluoroquinolones)]; Pfizer; Alexion;
ATYR Pharma; Genzyme/Sanofi; Synageva [DSMB for drug products under development]; Merck [Allergen
immunotherapy products (Oral tablets for allergen immunotherapy)]. Equity Ownership/Stock Options:
AllerQuest [Penicillin allergy diagnosis (Penicilloyl polylysine)]; DBV Tech [Epicutaneous immunotherapy
(Viaskin patches)]. Anna M Feldweg, MD Nothing to disclose.
Contributor disclosures are reviewed for conflicts of interest by the editorial group. When found, these are
addressed by vetting through a multilevel review process, and through requirements for references to be
provided to support the content. Appropriately referenced content is required of all authors and must
conform to UpToDate standards of evidence.
Conflict of interest policy

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