Cited by 197Analytical Methods in PharmaceuticalsPhysical Organic Chemistry and Reaction KineticsAntibiotics Pharmacokinetics and Efficacy

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Comparison of the acid stability of azithromycin and erythromycin A

Fiese, E. F., Steffen, S. H.·1990·Journal of Antimicrobial Chemotherapy

DOI 10.1093/jac/25.suppl_a.39

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Abstract

In acidic aqueous media, erythromycin A is rapidly degraded via intramolecular dehydration to form erythromycin-6.9-hemiketal and then anhydroerythromycin, both of which possess little antimicrobial activity. Azithromycin, a new azalide antibiotic, has a methyl-substituted nitrogen in place of the carbonyl at the 9a position of the aglycone ring, thus blocking the internal dehydration pathway. As a result, azithromycin decomposition occurs primarily via acid-catalysed hydrolysis of the ether bond to the neutral cladinose sugar. Rate constants and the time for 10% decay (T1/10) were determined for both azithromycin and erythromycin A at pH2 using various levels of acetonitrile cosolvent and constant ionic strength. Semi-log plots of the decay rate constants versus the reciprocal of the solution dielectric constants were used to extrapolate to totally aqueous conditions. In solution at 37 degrees C and pH2 with ionic strength mu = 0.02, azithromycin was degraded with a T1/10 of 20.1 min while erythromycin underwent 10% decay in only 3.7 sec. The activation energy for hydrolysis of the ether bond connecting cladinose to azithromycin was 25.3 kcal/mol while the internal dehydration reaction of erythromycin had an activation energy of 15.6 kcal/mol. A solution stability profile was generated for azithromycin over the pH range of 1.0 to 4.1 at 30 degrees C. Stability was found to improve ten-fold for each unit increase in pH.

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Background
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“Macrolide antibiotics (MAs) contain eight types of VAs: roxithromycin (RTM), azithromycin (AZI), tilmicosin (TIL), kitasamycin (KSM), erythromycin (ERY), tylosin (TYL), gamithromycin (GAM) and midecamycin (MDM).”
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“The second generation predominantly features modi ﬁ cations at the C6 and C9 positions (e.g., clari-thromycin, azithromycin) to improve acid stability, and in general they exhibit better bioavailability and tissue penetration than ﬁ rst-generation macrolides [2, 12, 44, 45].”

Authors: Fiese, E. F., & Steffen, S. H.
Affiliations: Pfizer (United States) (US)
Venue: Journal of Antimicrobial Chemotherapy
Publisher: Oxford University Press (OUP)
Published: 1990-01-01
Volume: 25
Issue: suppl A
Pages: 39-47
ISSN: 0305-7453 (ISSN-L)
1460-2091
DOI: 10.1093/jac/25.suppl_a.39
OpenAlex: W2052427658
Cited by: 197
References: 0
Citations by year: 2026: 2 · 2025: 6 · 2024: 7 · 2023: 2 · 2022: 6 · 2021: 4 · 2020: 2 · 2019: 3 · 2018: 10 · 2017: 8 · 2016: 5 · 2015: 5 · 2014: 6 · 2013: 5 · 2012: 2
FWCI: 16.36
Type: journal article
Language: en
Open access: closed
Locations: Journal of Antimicrobial Chemotherapy (publishedVersion)
PubMed (publishedVersion)
Topics: Physical Sciences › Chemistry › Analytical Chemistry › Analytical Methods in Pharmaceuticals
Physical Sciences › Chemistry › Organic Chemistry › Physical Organic Chemistry and Reaction Kinetics
Health Sciences › Medicine › Pharmacology (medical) › Antibiotics Pharmacokinetics and Efficacy
Keywords: azithromycin, erythromycin A, acid stability, intramolecular dehydration, azalide antibiotics, activation energy, pH dependence, solution stability, dielectric constant
MeSH terms: Acetonitriles, Chromatography, High Pressure Liquid, Drug Stability, Erythromycin, Hydrogen-Ion Concentration, Hydrolysis, Azithromycin

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Comparison of the acid stability of azithromycin and erythromycin A

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