Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C38H72N2O12 |
Molecular Weight | 748.9845 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 18 / 18 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
InChI
InChIKey=MQTOSJVFKKJCRP-BICOPXKESA-N
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
Azithromycin is one of the world's best-selling antibiotics, used to treat or prevent certain bacterial infections: Acute bacterial exacerbations of chronic bronchitis in adults; acute bacterial sinusitis in adults; uncomplicated skin and skin structure infections in adults; urethritis and cervicitis in adults; genital ulcer disease in men; acute otitis media in pediatric patients; community-acquired pneumonia in adults and pediatric patients; pharyngitis/tonsillitis in adults and pediatric patients. Azithromycin should not be used in patients with pneumonia who are judged inappropriate for oral therapy because of moderate to severe illness or risk factors. A team of researchers at the Croatian pharmaceutical company Pliva, discovered azithromycin in 1980. It was patented in 1981. In 1986, Pliva and Pfizer signed a licensing agreement, which gave Pfizer exclusive rights for the sale of azithromycin in Western Europe and the United States. Pliva put its azithromycin on the market in Central and Eastern Europe under the brand name of Sumamed in 1988. Pfizer launched azithromycin under Pliva's license in other markets under the brand name Zithromax in 1991. Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half-life, which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Intravenous azithromycin-induced ototoxicity. | 1999 Feb |
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Pharyngeal colonization prevalence rates for Streptococcus pyogenes and Streptococcus pneumoniae in a respiratory chemoprophylaxis intervention study using azithromycin. | 2000 Jan |
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In vitro susceptibilities of rapidly growing mycobacteria to telithromycin (HMR 3647) and seven other antimicrobials. | 2000 Jan |
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Apoptosis, oxidative metabolism and interleukin-8 production in human neutrophils exposed to azithromycin: effects of Streptococcus pneumoniae. | 2000 Jul |
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Comparison of azithromycin and doxycycline in the treatment of erythema migrans. | 2000 May-Jun |
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Breakthrough pneumococcal bacteremia in patients being treated with azithromycin and clarithromycin. | 2000 Oct |
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Potentially fatal interaction between azithromycin and disopyramide. | 2000 Sep |
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Antibiotic prophylaxis for intrauterine contraceptive device insertion. | 2001 |
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Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens. | 2001 |
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The SAFE strategy for the elimination of trachoma by 2020: will it work? | 2001 |
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Comparison of two azithromycin distribution strategies for controlling trachoma in Nepal. | 2001 |
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[Skin eruptions due to azithromycin (Azadose-Zithromax) and infectious mononucleosis]. | 2001 Apr |
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Mycobacterium marinum infection in a lung transplant recipient. | 2001 Apr |
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Incidence and determinants of Pseudomonas aeruginosa infection among persons with HIV: association with hospital exposure. | 2001 Apr |
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Comparative efficacy of new investigational agents against Helicobacter pylori. | 2001 Apr |
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Efficacy, safety and tolerability of 3 day azithromycin versus 10 day co-amoxiclav in the treatment of children with acute lower respiratory tract infections. | 2001 Apr |
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Six cases of confluent and reticulated papillomatosis alleviated by various antibiotics. | 2001 Apr |
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Severe babesiosis in Long Island: review of 34 cases and their complications. | 2001 Apr 15 |
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[Isolation of Vibrio strains in French coastal waters and infection with Vibrio cholerae non-O1/non-O139]. | 2001 Apr 7 |
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Identification of parasitoses in a child burial from Adak Island (Central Aleutian Islands, Alaska). | 2001 Feb |
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[Subacute infectious endocarditis due to the agent of cat scratch fever: Bartonella henselae]. | 2001 Feb |
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Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries. | 2001 Jan |
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Activity of buforin II alone and in combination with azithromycin and minocycline against Cryptosporidium parvum in cell culture. | 2001 Jan |
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Serum and WBC pharmacokinetics of 1500 mg of azithromycin when given either as a single dose or over a 3 day period in healthy volunteers. | 2001 Jan |
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Resolution of cyclosporine-induced gingival hyperplasia resistant to azithromycin by switching to tacrolimus. | 2001 Jan |
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Activity of moxifloxacin by itself and in combination with ethambutol, rifabutin, and azithromycin in vitro and in vivo against Mycobacterium avium. | 2001 Jan |
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Effect of azithromycin on murine arteriosclerosis exacerbated by Chlamydia pneumoniae. | 2001 Jan 15 |
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Chlamydia pneumoniae infection in circulating human monocytes is refractory to antibiotic treatment. | 2001 Jan 23 |
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Donovanosis: an update. | 2001 Jul |
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Malaria chemoprophylaxis in the age of drug resistance. I. Currently recommended drug regimens. | 2001 Jul 15 |
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Inhibitory and bactericidal effects of telithromycin (HMR 3647, RU 56647) and five comparative antibiotics, used singly and in combination, against vancomycin-resistant and vancomycin-susceptible enterococci. | 2001 Jul-Aug |
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The hidden impact of antibacterial resistance in respiratory tract infection. Re-evaluating current antibiotic therapy. | 2001 Jun |
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A randomized controlled trial comparing amoxicillin and azithromycin for the treatment of Chlamydia trachomatis in pregnancy. | 2001 Jun |
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Susceptibility of Canadian isolates of Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pneumoniae to oral antimicrobial agents. | 2001 Jun |
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The effect of azithromycin and clarithromycin on ex vivo interleukin-8 (IL-8) release from whole blood and IL-8 production by human alveolar macrophages. | 2001 Jun |
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Insights into the mechanism of azithromycin interaction with an Escherichia coli functional ribosomal complex. | 2001 Jun |
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Azithromycin-containing regimens for treatment of Mycobacterium avium complex lung disease. | 2001 Jun 1 |
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A family cluster of Chlamydia trachomatis infection. | 2001 Jun 16 |
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Postantibiotic suppression effect of macrolides on the expression of flagellin in Pseudomonas aeruginosa and Proteus mirabilis. | 2001 Mar |
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In vitro susceptibility of recent clinical isolates of Chlamydia trachomatis to macrolides and tetracyclines. | 2001 Mar |
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Pharmacokinetic and safety profile of desloratadine and fexofenadine when coadministered with azithromycin: a randomized, placebo-controlled, parallel-group study. | 2001 Mar |
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Treatment outcomes in acute exacerbations of chronic bronchitis: comparison of macrolides and moxifloxacin from the patient perspective. | 2001 Mar-Apr |
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[Pharmacological and pharmacokinetic properties of azithromycin (Zithromac), a novel 15-membered ring macrolide antibacterial agent]. | 2001 May |
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The canine Purkinje fiber: an in vitro model system for acquired long QT syndrome and drug-induced arrhythmogenesis. | 2001 May |
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A multicenter study of the antimicrobial susceptibility of Haemophilus influenzae, Streptococcus pneumoniae, and Moraxella catarrhalis isolated from patients with community-acquired lower respiratory tract infections in 1999 in Portugal. | 2001 Spring |
Patents
Sample Use Guides
Community-acquired pneumonia (mild severity); Pharyngitis/tonsillitis (second-line therapy); Skin/skin structure (uncomplicated): 500 mg as a single dose on Day 1, followed by 250 mg once daily on Days 2 through 5. Acute bacterial exacerbations of chronic bronchitis (mild to moderate): 500 mg as a single dose on Day 1, followed by 250 mg once daily on Days 2 through 5 or 500 mg once daily for 3 days Acute bacterial sinusitis: 500 mg once daily for 3 days Genital ulcer disease (chancroid) Non-gonococcal urethritis and cervicitis: One single 1 gram dose. Gonococcal urethritis and cervicitis: One single 2 gram dose. Acute otitis media: 30 mg/kg as a single dose or 10 mg/kg once daily for 3 days or 10 mg/kg as a single dose on Day
Route of Administration:
Oral
Azithromycin can benefit treating allergic airway inflammation and remodeling. Azithromycin significantly reduced the inflammation score, peribronchial smooth muscle layer thickness, epithelial thickening and goblet cell metaplasia, and effectively suppressed apoptotic index (AI) of airway epithelium. Moreover, the increasing mRNA and protein expressions of Caspase-3 and Bax/Bcl-2 ratio in lung tissue were all significantly decreased in azithromycin-treated rats. In vitro, azithromycin significantly suppressed TGF-β1-induced BEAS-2B cells apoptosis and reversed TGF-β1 elevated Caspase-3 mRNA level and Bax/Bcl-2 ratio.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
J01FA10
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NDF-RT |
N0000175935
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NCI_THESAURUS |
C261
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Code System | Code | Type | Description | ||
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83905-01-5
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DB00207
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83905-01-5
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PRIMARY | |||
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C76213
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PRIMARY | |||
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83905-01-5
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PRIMARY | |||
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M2177
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PRIMARY | Merck Index | ||
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6197
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83905-01-5
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SUB90954
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SUB05660MIG
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447043
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1299904
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PRIMARY | RxNorm |
ACTIVE MOIETY
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