Comparison of the acid stability of azithromycin and erythromycin A
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
Cites
Statistics
Claims the paper makes
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?
Many antibiotics, including ERY, degrade more rapidly under acidic conditions.
“In contrast, many antibiotics, including ERY, degrade more rapidly under acidic conditions (Fiese and Steffen 1990; Ismaiel et al. 2016).”
From Integrated morpho-physiological and biochemical description of the mechanisms leading stress responses in cyanobacteria (Arthrospira platensis) upon exposure to Erythromycin (2025) · cites this paper as Fiese and Steffen 1990
A. platensis thrives in alkaline environments, which can help preserve the stability of ERY.
“Furthermore, A. platensis thrives in alkaline environments, which can help preserve the stability of ERY.”
From Integrated morpho-physiological and biochemical description of the mechanisms leading stress responses in cyanobacteria (Arthrospira platensis) upon exposure to Erythromycin (2025) · cites this paper as Fiese and Steffen 1990
Cited by
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 · see citing works
Peters, D. H., Friedel, H. A., & McTavish, D. (1992) · Drugs · doi:10.2165/00003495-199244050-00007 · Cited by 305 · see citing works
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 · see citing works
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 · see citing works
From Erythromycin to Azithromycin and New Potential Ribosome-Binding Antimicrobials
Jelić, D., & Antolović, R. (2016) · Antibiotics · doi:10.3390/antibiotics5030029 · Cited by 203 · see citing works
“Azithromycin proved to be highly superior to that of erythromycin, relative to stability in acidic conditions [62].”
BackgroundAnalysis 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 · see citing works
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 · see citing works
Azithromycin Clinical Pharmacokinetics
Lalak, N. J., & Morris, D. L. (1993) · Clinical Pharmacokinetics · doi:10.2165/00003088-199325050-00003 · Cited by 155 · see citing works
Jones, H. M., Parrott, N. J., Ohlenbusch, G., & Lav, T. (2006) · Clinical Pharmacokinetics · doi:10.2165/00003088-200645120-00006 · Cited by 149 · see citing works
Dunn, C. J., & Barradell, L. B. (1996) · Drugs · doi:10.2165/00003495-199651030-00013 · Cited by 149 · see citing works
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 · see citing works
Azithromycin: The First Azalide Antibiotic
Ballow, C. H., & Amsden, G. W. (1992) · Annals of Pharmacotherapy · doi:10.1177/106002809202601014 · Cited by 126 · see citing works
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 · see citing works
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 · see citing works
“By comparison, degradation of azithromycin takes 20 min [9].”
BackgroundThe pharmacokinetics of azithromycin and their clinical significance
Lode, H. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975832 · Cited by 107 · see citing works
“7 seconds while 10 % azithromycin decay is observed in 20 minutes (4).”
BackgroundThe 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 102 · see citing works
“For example, macrolide antibiotics rapidly degrade under acidic conditions (Fiese and Steffen, 1990; Kristl and Vrečer, 2000; Nakagawa et al., 1992).”
BackgroundGomi, K., Yashima, A., Nagano, T., et al. (2007) · Journal of Periodontology · doi:10.1902/jop.2007.060247 · Cited by 102 · see citing works
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 · see citing works
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 · see citing works
Effects of food on drug absorption
Welling, P. G. (1989) · Pharmacology & Therapeutics · doi:10.1016/0163-7258(89)90019-3 · Cited by 94 · see citing works
Amacher, D. E., Schomaker, S., & Retsema, J. A. (1991) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.35.6.1186 · Cited by 87 · see citing works
“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).”
BackgroundFohner, A. E., Sparreboom, A., Altman, R. B., et al. (2017) · Pharmacogenetics and Genomics · doi:10.1097/fpc.0000000000000270 · Cited by 81 · see citing works
Voigt, M., & Jaeger, M. (2017) · Sustainable Chemistry and Pharmacy · doi:10.1016/j.scp.2016.12.001 · Cited by 78 · see citing works
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 · see citing works
Azalides from Azithromycin to New Azalide Derivatives
Mutak, S. (2007) · The Journal of Antibiotics · doi:10.1038/ja.2007.10 · Cited by 75 · see citing works
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 · see citing works
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 · see citing works
Brown, B. A., Griffith, D. E., Girard, W., et al. (1997) · Clinical Infectious Diseases · doi:10.1093/clinids/24.5.958 · Cited by 73 · see citing works
“The azalides contain a methyl-substituted nitrogenatom in place of the carbonyl at the 9a position in the macrolide aglycone ring [13, 14].”
BackgroundGenome 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 71 · see citing works
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 · see citing works
Cyphert, E. L., Wallat, J. D., Pokorski, J. K., et al. (2017) · Antibiotics · doi:10.3390/antibiotics6020011 · Cited by 69 · see citing works
“site where the intramolecular dehydration chemical conversion reaction of EM originates [19].”
InfluentialDisposition 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 · see citing works
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 · see citing works
Rodvold, K. A., & Piscitelli, S. C. (1993) · Clinical Infectious Diseases · doi:10.1093/clinids/17.supplement_1.s192 · Cited by 67 · see citing works
“Azithromycin is acid stable and has a bioavailability of -37% [10-12, 15].”
BackgroundAzithromycin 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 · see citing works
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 · see citing works
Principi, N. (1995) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01690872 · Cited by 63 · see citing works
“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.”
BackgroundBAHRAMI, G., MIRZAEEI, S., & KIANI, A. (2005) · Journal of Chromatography B · doi:10.1016/j.jchromb.2005.03.042 · Cited by 62 · see citing works
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 · see citing works
Bartold, P. M., BOIS, A. H. D., Gannon, S. C., et al. (2013) · Inflammopharmacology · doi:10.1007/s10787-012-0165-1 · Cited by 52 · see citing works
“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).”
BackgroundProphylactic 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 · see citing works
“First, it has better stability than erythromycin in the presence of acidic pH (2), leading to good digestive absorption.”
BackgroundLoo, V. G., Sherman, P. M., & Matlow, A. (1992) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.36.5.1133 · Cited by 49 · see citing works
“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).”
BackgroundA 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 · see citing works
Total Synthesis of Azithromycin
Kim, H. C., & Kang, S. H. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200805334 · Cited by 48 · see citing works
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 · see citing works
Dyab, A. K. F., Mohamed, M. A., Meligi, N. M., et al. (2018) · RSC Advances · doi:10.1039/c8ra05499a · Cited by 45 · see citing works
Li, B., Adams, E., Schepdael, A. V., & Hoogmartens, J. (2005) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.2317 · Cited by 45 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
Beghi, G., Berni, F., Carratù, L., et al. (1995) · Journal of Chemotherapy · doi:10.1179/joc.1995.7.2.146 · Cited by 42 · see citing works
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 · see citing works
Dalhoff, A., Schubert, S., & Ullmann, U. (2005) · Infection · doi:10.1007/s15010-005-8206-y · Cited by 39 · see citing works
“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].”
BackgroundThe 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 · see citing works
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 · see citing works
“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.”
BackgroundTime-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 · see citing works
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 · see citing works
“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 · see citing works
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 · see citing works
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 · see citing works
Debremaeker, D., Visky, D., Chepkwony, H. K., et al. (2003) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.917 · Cited by 37 · see citing works
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 · see citing works
“In vivo, not only is the doubling rate likely longer, but amoxicillin efficacy is further compromised by the gastric acidic pH (7, 16).”
BackgroundChandra, R., Liu, P., Breen, J. D., et al. (2007) · Clinical Pharmacokinetics · doi:10.2165/00003088-200746030-00005 · Cited by 33 · see citing works
Gynaecological tissue levels of azithromycin
Krohn, K. (1991) · European Journal of Clinical Microbiology & Infectious Diseases · doi:10.1007/bf01975844 · Cited by 33 · see citing works
“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).”
BackgroundAzithromycin: 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 · see citing works
Daniel, R., & European Azithromycin Study Group (1991) · Journal of International Medical Research · doi:10.1177/030006059101900503 · Cited by 32 · see citing works
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 · see citing works
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 · see citing works
Laurent, K. (1996) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/37.suppl_c.115 · Cited by 28 · see citing works
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 · see citing works
Amin, F., Khan, S., Shah, S. M. H., et al. (2018) · Drug Design Development and Therapy · doi:10.2147/dddt.s183534 · Cited by 26 · see citing works
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 · see citing works
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 · see citing works
Zachariah, J. (1996) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/37.suppl_c.103 · Cited by 25 · see citing works
Bryskier, A., & Denis, A. (2002) · Birkhäuser Basel eBooks · doi:10.1007/978-3-0348-8105-0_7 · Cited by 24 · see citing works
Vajdle, O., Guzsvány, V., Škorić, D., et al. (2016) · Electrochimica Acta · doi:10.1016/j.electacta.2015.12.207 · Cited by 23 · see citing works
“In acidic medium – which is presented in the stomach – erythromycin is unstable, forming degradation products which exhibit lower antimicrobial activity [2, 7].”
BackgroundActivities 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 · see citing works
“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).”
BackgroundAzithromycin–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 · see citing works
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 · see citing works
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 · see citing works
“a high degree of cell penetration (2, 4, 27).”
BackgroundMacrolide 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 · see citing works
“Azithromycin is a 15-membered synthetic derivative of erythromycin A and has a methyl group at position 9a [10].”
BackgroundMallegol, J., FERNANDES, P. B., Seah, C., et al. (2013) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.00564-13 · Cited by 21 · see citing works
“Unlike erythromycin, the 15-member azalide ring of azithromycin is acid stable (15).”
BackgroundElimination 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 · see citing works
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 · see citing works
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 · see citing works
“By comparison, degradation of AZM takes 20 min [20].”
BackgroundCuratolo, W. J., Liu, P., Johnson, B., et al. (2011) · Pharmaceutical Research · doi:10.1007/s11095-011-0386-9 · Cited by 19 · see citing works
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 · see citing works
Azithromycin and novel azalides
Schönfeld, W., & Mutak, S. (2002) · Birkhäuser Basel eBooks · doi:10.1007/978-3-0348-8105-0_6 · Cited by 19 · see citing works
Blandizzi, C. (1998) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/42.1.75 · Cited by 19 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
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 · see citing works
Hamzehloo, M., Karimi, J., Eghbali, N., et al. (2017) · Drying Technology · doi:10.1080/07373937.2016.1269807 · Cited by 17 · see citing works
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 · see citing works
“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].”
BackgroundThe 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 · see citing works
- 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
- 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 › Chemical Reaction Mechanisms
- Health Sciences › Medicine › Pharmacology › 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
