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

The DOI matches its Crossref record.

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

Open this paper in CoChat — free account

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.

Integrity signals

Registry

Crossref · 10.1093/jac/25.suppl_a.39

Cites

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Sorted by citations

Pharmaceutical solvates, hydrates and amorphous forms: A special emphasis on cocrystals
Healy, A. M., Worku, Z. A., Kumar, D. K., et al. (2017) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2017.03.002 · Cited by 371
Azithromycin
Peters, D. H., Friedel, H. A., & McTavish, D. (1992) · Drugs · doi:10.2165/00003495-199244050-00007 · Cited by 305
The Macrolides: Erythromycin, Clarithromycin, and Azithromycin
Alvarez-Elcoro, S., & Enzler, M. J. (1999) · Mayo Clinic Proceedings · doi:10.4065/74.6.613 · Cited by 285
Tissue-directed pharmacokinetics
Schentag, J. J., & Ballow, C. H. (1991) · The American Journal of Medicine · doi:10.1016/0002-9343(91)90394-d · Cited by 203
From Erythromycin to Azithromycin and New Potential Ribosome-Binding Antimicrobials
Jelić, D., & Antolović, R. (2016) · Antibiotics · doi:10.3390/antibiotics5030029 · Cited by 203
“Azithromycin proved to be highly superior to that of erythromycin, relative to stability in acidic conditions [62].”
Background
Analysis of macrolide antibiotics
Kanfer, I., Skinner, M., & Walker, R. B. (1998) · Journal of Chromatography A · doi:10.1016/s0021-9673(98)00276-3 · Cited by 180
Azithromycin--review of key chemical, pharmacokinetic and microbiological features
Lode, H. M., Börner, K., Koeppe, P., et al. (1996) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/37.suppl_c.1 · Cited by 158
Azithromycin Clinical Pharmacokinetics
Lalak, N. J., & Morris, D. L. (1993) · Clinical Pharmacokinetics · doi:10.2165/00003088-199325050-00003 · Cited by 155
Predicting Pharmacokinetic Food Effects Using Biorelevant Solubility Media and Physiologically Based Modelling
Jones, H. M., Parrott, N. J., Ohlenbusch, G., & Lav, T. (2006) · Clinical Pharmacokinetics · doi:10.2165/00003088-200645120-00006 · Cited by 150
Azithromycin
Dunn, C. J., & Barradell, L. B. (1996) · Drugs · doi:10.2165/00003495-199651030-00013 · Cited by 149
Pharmacokinetics of azithromycin in rats and dogs
Shepard, R. M., & Falkner, F. C. (1990) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/25.suppl_a.49 · Cited by 136
Azithromycin: The First Azalide Antibiotic
Ballow, C. H., & Amsden, G. W. (1992) · Annals of Pharmacotherapy · doi:10.1177/106002809202601014 · Cited by 126
Azithromycin—Spectrum of Activity, Pharmacokinetics, and Clinical Applications
Drew, R. H., & Gallis, H. A. (1992) · Pharmacotherapy The Journal of Human Pharmacology and Drug Therapy · doi:10.1002/j.1875-9114.1992.tb04504.x · Cited by 122
Macrolides: structures and microbial targets
Retsema, J. A., & Fu, W. (2001) · International Journal of Antimicrobial Agents · doi:10.1016/s0924-8579(01)00401-0 · Cited by 115
“By comparison, degradation of azithromycin takes 20 min [9].”
Background
The pharmacokinetics of azithromycin and their clinical significance
Lode, H. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975832 · Cited by 107
“7 seconds while 10 % azithromycin decay is observed in 20 minutes (4).”
Background
The dynamic gastric environment and its impact on drug and formulation behaviour
Abeele, J. V. D., Rubbens, J., Brouwers, J., & Augustijns, P. (2016) · European Journal of Pharmaceutical Sciences · doi:10.1016/j.ejps.2016.08.060 · Cited by 107
“For example, macrolide antibiotics rapidly degrade under acidic conditions (Fiese and Steffen, 1990; Kristl and Vrečer, 2000; Nakagawa et al., 1992).”
Background
Effects of Full‐Mouth Scaling and Root Planing in Conjunction With Systemically Administered Azithromycin
Gomi, K., Yashima, A., Nagano, T., et al. (2007) · Journal of Periodontology · doi:10.1902/jop.2007.060247 · Cited by 102
Azithromycin and Clarithromycin Overview and Comparison With Erythromycin
Scheld, W. M., Whitman, M. S., & Tunkel, A. R. (1992) · Infection Control and Hospital Epidemiology · doi:10.1086/646545 · Cited by 100
High-performance liquid chromatographic assay with electrochemical detection for azithromycin in serum and tissues
Shepard, R. M., Duthu, G. S., Ferraina, R. A., et al. (1991) · Journal of Chromatography B Biomedical Sciences and Applications · doi:10.1016/0378-4347(91)80393-q · Cited by 95
Effects of food on drug absorption
Welling, P. G. (1989) · Pharmacology & Therapeutics · doi:10.1016/0163-7258(89)90019-3 · Cited by 94
Comparison of the effects of the new azalide antibiotic, azithromycin, and erythromycin estolate on rat liver cytochrome P-450
Amacher, D. E., Schomaker, S., & Retsema, J. A. (1991) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.35.6.1186 · Cited by 87
“This modification has resulted in improved stability at a low pH (9), improved potency against gram-negative organisms (19), and excellent in vivo activity against localized infections because of the high sustained tissue levels produced by azithromycin (10, 11).”
Background
PharmGKB summary
Fohner, A. E., Sparreboom, A., Altman, R. B., et al. (2017) · Pharmacogenetics and Genomics · doi:10.1097/fpc.0000000000000270 · Cited by 81
On the photodegradation of azithromycin, erythromycin and tylosin and their transformation products – A kinetic study
Voigt, M., & Jaeger, M. (2017) · Sustainable Chemistry and Pharmacy · doi:10.1016/j.scp.2016.12.001 · Cited by 78
Azithromycin and Clarithromycin: Overview and Comparison with Erythromycin
Whitman, M. S., & Tunkel, A. R. (1992) · Infection Control and Hospital Epidemiology · doi:10.2307/30147135 · Cited by 76
Azalides from Azithromycin to New Azalide Derivatives
Mutak, S. (2007) · The Journal of Antibiotics · doi:10.1038/ja.2007.10 · Cited by 75
Azithromycin: the first of the tissue-selective azalides
Hoepelman, I. M., & Schneider, M. M. E. (1995) · International Journal of Antimicrobial Agents · doi:10.1016/0924-8579(95)00009-w · Cited by 74
Insight into antibiotics removal: Exploring the photocatalytic performance of a Fe3O4/ZnO nanocomposite in a novel magnetic sequential batch reactor
Fernández, L., Gamallo, M., Gómez, M. A. G., Vázquez‐Vázquez, C., Rivas, J. M., Pintado, M., & Moreira, M. T. (2019) · Journal of Environmental Management · doi:10.1016/j.jenvman.2019.02.089 · Cited by 75
Relationship of Adverse Events to Serum Drug Levels in Patients Receiving High-Dose Azithromycin for Mycobacterial Lung Disease
Brown, B. A., Griffith, D. E., Girard, W., et al. (1997) · Clinical Infectious Diseases · doi:10.1093/clinids/24.5.958 · Cited by 73
“The azalides contain a methyl-substituted nitrogenatom in place of the carbonyl at the 9a position in the macrolide aglycone ring [13, 14].”
Background
Genome Engineering of Eubacterium limosum Using Expanded Genetic Tools and the CRISPR-Cas9 System
Shin, J., Kang, S., Song, Y., Jin, S., Lee, J. S., Lee, J.-K., Kim, D. R., Kim, S. C., Cho, S., & Cho, B. (2019) · ACS Synthetic Biology · doi:10.1021/acssynbio.9b00150 · Cited by 69
A kinetic study on the degradation of erythromycin A in aqueous solution
Kim, Y., Heinze, T. M., Beger, R. D., et al. (2003) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2003.10.023 · Cited by 69
Erythromycin Modification That Improves Its Acidic Stability while Optimizing It for Local Drug Delivery
Cyphert, E. L., Wallat, J. D., Pokorski, J. K., et al. (2017) · Antibiotics · doi:10.3390/antibiotics6020011 · Cited by 69
“site where the intramolecular dehydration chemical conversion reaction of EM originates [19].”
Influential
Disposition of oral azithromycin in humans*
Luke, D. R., & Foulds, G. H. (1997) · Clinical Pharmacology & Therapeutics · doi:10.1016/s0009-9236(97)90098-9 · Cited by 69
Bronchopulmonary Disposition of the Ketolide Telithromycin (HMR 3647)
Muller‐Serieys, C., Soler, P., Cantalloube, C., et al. (2001) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.45.11.3104-3108.2001 · Cited by 68
New Oral Macrolide and Fluoroquinolone Antibiotics: An Overview of Pharmacokinetics, Interactions, and Safety
Rodvold, K. A., & Piscitelli, S. C. (1993) · Clinical Infectious Diseases · doi:10.1093/clinids/17.supplement_1.s192 · Cited by 67
“Azithromycin is acid stable and has a bioavailability of -37% [10-12, 15].”
Background
Azithromycin and amoxicillin in the treatment of acute maxillary sinusitis
Casiano, R. R. (1991) · The American Journal of Medicine · doi:10.1016/0002-9343(91)90398-h · Cited by 65
A short review of human exposure to antibiotics based on urinary biomonitoring
Hu, Y., Zhu, Q., Wang, Y., Liao, C., & Jiang, G. (2022) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2022.154775 · Cited by 61
Multicentre comparative study of the efficacy and safety of azithromycin compared with amoxicillin/clavulanic acid in the treatment of paediatric patients with otitis media
Principi, N. (1995) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01690872 · Cited by 63
“The inclusion of a methyl-substituted nitrogen replacing the carbonyl in the aglycone ring, however, results in increased stability in acidic solutions and increased bioavailability compared with erythromycin (1) and may provide a partial explanation for the distinctive pharmacokinetic profile of azithromycin.”
Background
High performance liquid chromatographic determination of azithromycin in serum using fluorescence detection and its application in human pharmacokinetic studies
BAHRAMI, G., MIRZAEEI, S., & KIANI, A. (2005) · Journal of Chromatography B · doi:10.1016/j.jchromb.2005.03.042 · Cited by 62
Clinical Pharmacokinetic Properties of the Macrolide Antibiotics
Periti, P., Mazzei, T., Mini, E., et al. (1989) · Clinical Pharmacokinetics · doi:10.2165/00003088-198916050-00001 · Cited by 59
Antibacterial and immunomodulatory properties of azithromycin treatment implications for periodontitis
Bartold, P. M., BOIS, A. H. D., Gannon, S. C., et al. (2013) · Inflammopharmacology · doi:10.1007/s10787-012-0165-1 · Cited by 52
“Azithromycin is approximately 300 times more acid stable than erythromycin, which results in improved uptake, less gastrointestinal problems than erythromycin and its uptake is not dependent on concurrent food intake (Fiese and Steffen 1990; Foulds et al. 1996; Langley et al. 2004).”
Background
Prophylactic and therapeutic activities of azithromycin in a mouse model of pneumococcal pneumonia
Azoulay-Dupuis, E., Vallee, E., Bédos, J. P., et al. (1991) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.35.6.1024 · Cited by 51
“First, it has better stability than erythromycin in the presence of acidic pH (2), leading to good digestive absorption.”
Background
Helicobacter pylori infection in a pediatric population: in vitro susceptibilities to omeprazole and eight antimicrobial agents
Loo, V. G., Sherman, P. M., & Matlow, A. (1992) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.36.5.1133 · Cited by 49
“Relative to erythromycin, it has greater acid stability and a longer half-life and can achieve high concentrations in tissue with oral dosing (10, 11).”
Background
A miniature mass spectrometer for liquid chromatography applications
Malcolm, A., Wright, S. L., Syms, R. R. A., et al. (2011) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.5230 · Cited by 48
Total Synthesis of Azithromycin
Kim, H. C., & Kang, S. H. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200805334 · Cited by 48
Concentrations of azithromycin in human tonsillar tissue
Foulds, G. H., Chan, K. H., Johnson, J. T., et al. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975840 · Cited by 46
Encapsulation of erythromycin and bacitracin antibiotics into natural sporopollenin microcapsules: antibacterial, cytotoxicity, in vitro and in vivo release studies for enhanced bioavailability
Dyab, A. K. F., Mohamed, M. A., Meligi, N. M., et al. (2018) · RSC Advances · doi:10.1039/c8ra05499a · Cited by 45
Analysis of unknown compounds in gentamicin bulk samples with liquid chromatography coupled with ion trap mass spectrometry
Li, B., Adams, E., Schepdael, A. V., & Hoogmartens, J. (2005) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.2317 · Cited by 45
Effects of environmental factors on the in vitro potency of azithromycin
Retsema, J. A., Brennan, L. A., & Girard, A. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975836 · Cited by 45
Determination of 18 antibiotics in urine using LC-QqQ-MS/MS
Huang, W., Qiu, Q., Chen, M., Shi, J., Huang, X., Kong, Q., Long, D., Chen, Z., & Yan, S. (2018) · Journal of Chromatography B · doi:10.1016/j.jchromb.2018.12.019 · Cited by 43
The Association of Erythromycin and Infantile Hypertrophic Pyloric Stenosis
Hauben, M., & Amsden, G. W. (2002) · Drug Safety · doi:10.2165/00002018-200225130-00004 · Cited by 44
Azithromycin concentrations in sinus fluid and mucosa after oral administration
Karma, P. H., Pukander, J., & Penttilä, M. A. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975841 · Cited by 44
An automated on-line turbulent flow liquid-chromatography technology coupled to a high resolution mass spectrometer LTQ-Orbitrap for suspect screening of antibiotic transformation products during microalgae wastewater treatment
Jaén-Gil, A., Hom-Díaz, A., Llorca, M., Vicent, T., Blánquez, P., Barceló, ‪., & Rodríguez‐Mozaz, S. (2018) · Journal of Chromatography A · doi:10.1016/j.chroma.2018.06.027 · Cited by 43
Synthesis and biological activity of 4″-O-acyl derivatives of 14- and 15-membered macrolides linked to ω-quinolone-carboxylic unit
Škugor, M. M., Štimac, V., Jakopović, I. P., Lugarić, Đ., Paljetak, H. Č., Filić, D., Modrić, M., Đilović, I., Gembarovski, D., Mutak, S., et al. (2010) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2010.06.050 · Cited by 43
Electrochemical oxidation of azithromycin and its derivatives
Mandić, Z., Weitner, Z., & Ilijaš, M. (2003) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/s0731-7085(03)00315-7 · Cited by 42
Efficacy and Tolerability of Azithromycin versus Amoxicillin/Clavulanic Acid in Acute Purulent Exacerbation of Chronic Bronchitis
Beghi, G., Berni, F., Carratù, L., et al. (1995) · Journal of Chemotherapy · doi:10.1179/joc.1995.7.2.146 · Cited by 42
Novel ureas and thioureas of 15-membered azalides with antibacterial activity against key respiratory pathogens
Krajačić, M. B., Novak, P., Dumić, M., et al. (2009) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2009.02.001 · Cited by 41
Effect of pH on the in Vitro Activity of and Propensity for Emergence of Resistance to Fluoroquinolones, Macrolides, and a Ketolide
Dalhoff, A., Schubert, S., & Ullmann, U. (2005) · Infection · doi:10.1007/s15010-005-8206-y · Cited by 39
“Consequently, in acidic medium, macrolide molecules are ionized which slows the entry of the molecule into bacterial cells, resulting in an increase in the MIC of the antibiotic [4–8].”
Background
The evolution and role of macrolides in infectious diseases
Blondeau, J. M. (2002) · Expert Opinion on Pharmacotherapy · doi:10.1517/14656566.3.8.1131 · Cited by 40
Formulation and biopharmaceutical evaluation of bitter taste masking microparticles containing azithromycin loaded in dispersible tablets
Tung, N.-T., Tran, C.-S., Nguyen, T.-L., et al. (2017) · European Journal of Pharmaceutics and Biopharmaceutics · doi:10.1016/j.ejpb.2017.03.017 · Cited by 39
“Besides, because a macrolide antibiotic like AZI is unstable in gastric medium [1,5], pH modulators were also screened and incorporated into the DTs for stability improvement of the drug.”
Background
Time-Resolved Binding of Azithromycin to Escherichia coli Ribosomes
Petropoulos, A. D., Kouvela, E. C., Starosta, A. L., Wilson, D. N., Dinos, G. P., & Kalpaxis, D. L. (2008) · Journal of Molecular Biology · doi:10.1016/j.jmb.2008.11.042 · Cited by 40
Improved detection of multiple environmental antibiotics through an optimized sample extraction strategy in liquid chromatography-mass spectrometry analysis
Yi, X., Bayen, S., Kelly, B. C., Li, X., & Zhou, Z. (2015) · Analytical and Bioanalytical Chemistry · doi:10.1007/s00216-015-9074-7 · Cited by 37
“1 min under the same conditions [47].”
Short-Term Treatment of Pertussis with Azithromycin in Infants and Young Children
Baće, A., Zrnić, T. I., Begovać, J., et al. (1999) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/s100960050281 · Cited by 38
The effect of ultrafiltration process on the fate of antibiotic-related microcontaminants, pathogenic microbes, and toxicity in urban wastewater.
Michael, S., Drigo, B., Michael-Kordatou, I., Michael, C., Jäger, T., Aleer, S. C., Schwartz, T., Donner, E., & Fatta-Kassinos, D. (2022) · Journal of Hazardous Materials · doi:10.1016/j.jhazmat.2022.128943 · Cited by 32
Azithromycin extraction from municipal wastewater and quantitation using liquid chromatography/mass spectrometry
Koch, D. E., Bhandari, A., Close, L., et al. (2005) · Journal of Chromatography A · doi:10.1016/j.chroma.2005.03.052 · Cited by 37
Analysis of unknown compounds in azithromycin bulk samples with liquid chromatography coupled to ion trap mass spectrometry
Debremaeker, D., Visky, D., Chepkwony, H. K., et al. (2003) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.917 · Cited by 37
The Oligo-Acyl Lysyl Antimicrobial Peptide C 12 K-2β 12 Exhibits a Dual Mechanism of Action and Demonstrates Strong In Vivo Efficacy against Helicobacter pylori
Makobongo, M. O., Gancz, H., Carpenter, B. M., McDaniel, D. P., & Merrell, D. S. (2011) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.00689-11 · Cited by 35
“In vivo, not only is the doubling rate likely longer, but amoxicillin efficacy is further compromised by the gastric acidic pH (7, 16).”
Background
Clinical Pharmacokinetics and Gastrointestinal Tolerability of a Novel Extended-Release Microsphere Formulation of Azithromycin
Chandra, R., Liu, P., Breen, J. D., et al. (2007) · Clinical Pharmacokinetics · doi:10.2165/00003088-200746030-00005 · Cited by 33
Gynaecological tissue levels of azithromycin
Krohn, K. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975844 · Cited by 33
“Azithromycin's relative stability in the acidic enVironment of the stomach is thought to contribute to its good oral bioavailability in comparison with erythromycin (6).”
Background
Azithromycin: a critical review of the first azilide antibiotic and its role in pediatric practice
Reed, M. D., & Blumer, J. L. (1997) · The Pediatric Infectious Disease Journal · doi:10.1097/00006454-199711000-00013 · Cited by 32
Simplified Treatment of Acute Lower Respiratory Tract Infection with Azithromycin: A Comparison with Erythromycin and Amoxycillin
Daniel, R., & European Azithromycin Study Group (1991) · Journal of International Medical Research · doi:10.1177/030006059101900503 · Cited by 32
The efficacy of azithromycin in the treatment of acute infraorbital space infection
Al-Belasy, F. A., & Hairam, A. R. (2003) · Journal of Oral and Maxillofacial Surgery · doi:10.1053/joms.2003.50063 · Cited by 31
Erythromycin encapsulation in nanoemulsion-based delivery systems for treatment of Helicobacter pylori infection: Protection and synergy
Tran, L. T. C., Gueutin, C., Frébourg, G., et al. (2017) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2017.09.060 · Cited by 28
Efficacy, safety and tolerability of azithromycin versus roxithromycin in the treatment of acute lower respiratory tract infections
Laurent, K. (1996) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/37.suppl_c.115 · Cited by 28
In Vitro Metabolism and Stability of the Actinide Chelating Agent 3,4,3-LI(1,2-HOPO)
Choi, T. A., Furimsky, A. M., Swezey, R. R., et al. (2015) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.24394 · Cited by 27
A new strategy for taste masking of azithromycin antibiotic: development, characterization, and evaluation of azithromycin titanium nanohybrid for masking of bitter taste using physisorption and panel testing studies
Amin, F., Khan, S., Shah, S. M. H., et al. (2018) · Drug Design Development and Therapy · doi:10.2147/dddt.s183534 · Cited by 26
Azithromycin potency determination: Optimal conditions for microbiological diffusion method assay
Turčinov, T., & Pepeljnjak, S. (1998) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/s0731-7085(97)00275-6 · Cited by 26
Degradation of high concentrations of azithromycin when present in a high organic content wastewater by using a continuously fed laboratory-scale UASB bioreactor
Martínez-Polanco, M. P., Valderrama-Rincón, J. A., Valderrama-Rincón, J. A., et al. (2021) · Chemosphere · doi:10.1016/j.chemosphere.2021.132191 · Cited by 25
A randomized, comparative study to evaluate the efficacy and tolerability of a 3-day course of azithromycin versus a 10-day course of co-amoxiclav as treatment of adult patients with lower respiratory tract infections
Zachariah, J. (1996) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/37.suppl_c.103 · Cited by 25
Ketolides: novel antibacterial agents designed to overcome resistance to erythromycin A within gram-positive cocci
Bryskier, A., & Denis, A. (2002) · Birkhäuser Basel eBooks · doi:10.1007/978-3-0348-8105-0_7 · Cited by 24
Voltammetric behavior of erythromycin ethylsuccinate at a renewable silver-amalgam film electrode and its determination in urine and in a pharmaceutical preparation
Vajdle, O., Guzsvány, V., Škorić, D., et al. (2016) · Electrochimica Acta · doi:10.1016/j.electacta.2015.12.207 · Cited by 23
“In acidic medium – which is presented in the stomach – erythromycin is unstable, forming degradation products which exhibit lower antimicrobial activity [2, 7].”
Background
Activities of β-Lactams and Macrolides against Helicobacter pylori
Hassan, I., Stark, R. M., Greenman, J., & Millar, M. R. (1999) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.43.6.1387 · Cited by 23
“The activities of macrolides have been known to be decreased at acidic pH, but the degree to which they are affected varies between members of this group of agents (12).”
Background
Azithromycin–sulfonamide conjugates as inhibitors of resistant Streptococcus pyogenes strains
Krajačić, M. B., Novak, P., Cindrić, M., et al. (2006) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2006.08.008 · Cited by 23
Azithromycin loaded on hydrogels of carbomer: Chemical stability and delivery properties
Esteban, S. L., Manzo, R. H., & Alovero, F. L. (2008) · International Journal of Pharmaceutics · doi:10.1016/j.ijpharm.2008.08.043 · Cited by 22
In vivo administration of azithromycin affects lymphocyte activity in vitro
Tomažič, J., Kotnik, V., & Wraber, B. (1993) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.37.9.1786 · Cited by 22
“a high degree of cell penetration (2, 4, 27).”
Background
Macrolide resistance in Streptococci and Haemophilus influenzae
Bozdoğan, B., & Appelbaum, P. C. (2004) · Clinics in Laboratory Medicine · doi:10.1016/j.cll.2004.03.006 · Cited by 22
“Azithromycin is a 15-membered synthetic derivative of erythromycin A and has a methyl group at position 9a [10].”
Background
Determination of In Vitro Activities of Solithromycin at Different pHs and Its Intracellular Activity against Clinical Isolates of Neisseria gonorrhoeae from a Laboratory Collection
Mallegol, J., FERNANDES, P. B., Seah, C., et al. (2013) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.00564-13 · Cited by 21
“Unlike erythromycin, the 15-member azalide ring of azithromycin is acid stable (15).”
Background
Elimination of macrolides in water bodies using photochemical oxidation
Voigt, M., Bartels, I., Nickisch‐Hartfiel, A., et al. (2018) · AIMS environmental science · doi:10.3934/environsci.2018.5.372 · Cited by 20
Synthesis and antibacterial activity of O-methylazithromycin derivatives.
Kobrehel, G., Lazarevski, G., Đokić, S., et al. (1992) · The Journal of Antibiotics · doi:10.7164/antibiotics.45.527 · Cited by 20
Azithromycin and lower respiratory tract infections
Blasi, F., Cazzola, M., Tarsia, P., et al. (2005) · Expert Opinion on Pharmacotherapy · doi:10.1517/14656566.6.13.2335 · Cited by 19
“By comparison, degradation of AZM takes 20 min [20].”
Background
Effects of Food on a Gastrically Degraded Drug: Azithromycin Fast-Dissolving Gelatin Capsules and HPMC Capsules
Curatolo, W. J., Liu, P., Johnson, B., et al. (2011) · Pharmaceutical Research · doi:10.1007/s11095-011-0386-9 · Cited by 19
Quantitative Thin-Layer Chromatographic Method of Analysis of Azithromycin in Pure and Capsule Forms
Khedr, A., & Sheha, M. (2003) · Journal of Chromatographic Science · doi:10.1093/chromsci/41.1.10 · Cited by 19
Azithromycin and novel azalides
Schönfeld, W., & Mutak, S. (2002) · Birkhäuser Basel eBooks · doi:10.1007/978-3-0348-8105-0_6 · Cited by 19
Gastric mucosal distribution and clinical efficacy of azithromycin in patients with Helicobacter pylori related gastritis
Blandizzi, C. (1998) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/42.1.75 · Cited by 19
Assignments of the 13C and 1H NMR spectra of azithromycin in CDCl3
Barber, J. (1991) · Magnetic Resonance in Chemistry · doi:10.1002/mrc.1260290719 · Cited by 19
pH-Dependent stability of azithromycin in aqueous solution and structure identification of two new degradation products
Saita, M. G., Aleo, D., Melilli, B., et al. (2018) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/j.jpba.2018.05.042 · Cited by 18
Pharmacokinetics of azithromycin after intravenous and intramuscular administration to goats
Cárceles, C. M., FONT, A., Espuny, A., et al. (2005) · Journal of Veterinary Pharmacology and Therapeutics · doi:10.1111/j.1365-2885.2004.00626.x · Cited by 18
Conformational analysis of the erythromycin analogues azithromycin and clarithromycin in aqueous solution and bound to bacterial ribosomes
Awan, A., Brennan, R. J., Regan, A. C., et al. (1995) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39950001653 · Cited by 18
A new blend of polymeric encapsulation of azithromycin by spray-drying with a pH responsive in drug release
Hamzehloo, M., Karimi, J., Eghbali, N., et al. (2017) · Drying Technology · doi:10.1080/07373937.2016.1269807 · Cited by 17
Comparative pharmacokinetics of macrolide antibiotics and concentrations achieved in polymorphonuclear leukocytes and saliva
Fassbender, M., Lode, H. M., Schiller, C., et al. (1996) · Clinical Microbiology and Infection · doi:10.1016/s1198-743x(15)60281-6 · Cited by 17
“Clarithromycin (CL), roxithromycin (RO), azithromycin (AZ) and dirithromycin (DI) have improved pharmacokinetic properties, especially high volumes of distribution and tissue concentrations, and improved acid stability [3,8,9].”
Background
The future role and importance of macrolides
Ball, P. D. (1991) · Journal of Hospital Infection · doi:10.1016/0195-6701(91)90217-v · Cited by 17

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

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Comparison of the acid stability of azithromycin and erythromycin A

Abstract

Overview

Integrity signals

Verification

Claims the paper makes

Claims other papers make about this one

Citations

Cited by

Related

Metadata

Record

About these checks