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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H72N2O12.2H2O
Molecular Weight 785.015
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZITHROMYCIN DIHYDRATE

SMILES

O.O.[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[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@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

InChI

InChIKey=SRMPHJKQVUDLQE-KUJJYQHYSA-N
InChI=1S/C38H72N2O12.2H2O/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;2*1H2/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-;;/m1../s1

HIDE SMILES / InChI
Molecular Formula C38H72N2O12
Molecular Weight 748.9845
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

1991
113
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8146
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8307
ZITHROMAX

Approved Use

Azithromycin Tablets, USP are indicated for the treatment of patients with mild to moderate infections (pneumonia: see WARNINGS ) caused by susceptible strains of the designated microorganisms in the specific conditions listed below. As recommended dosages, durations of therapy and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific dosing recommendations. Adults Acute bacterial exacerbations of chronic obstructive pulmonary disease due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Acute bacterial sinusitis due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. NOTE: Azithromycin should not be used in patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, elderly or debilitated patients, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Uncomplicated skin and skin structure infections due to Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus agalactiae. Abscesses usually require surgical drainage. Urethritis and cervicitis due to Chlamydia trachomatis or Neisseria gonorrhoeae. Genital ulcer disease in men due to Haemophilus ducreyi (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. Azithromycin, at the recommended dose, should not be relied upon to treat syphilis. Antimicrobial agents used in high doses for short periods of time to treat non-gonococcal urethritis may mask or delay the symptoms of incubating syphilis. All patients with sexually-transmitted urethritis or cervicitis should have a serologic test for syphilis and appropriate cultures for gonorrhea performed at the time of diagnosis. Appropriate antimicrobial therapy and follow-up tests for these diseases should be initiated if infection is confirmed. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly. To reduce the development of drug-resistant bacteria and maintain the effectiveness of azithromycin and other antibacterial drugs, azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Pediatric Patients: (See PRECAUTIONS—Pediatric Use and CLINICAL STUDIES IN PEDIATRIC PATIENTS .) Acute otitis media caused by Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Azithromycin should not be used in pediatric patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly.

Launch Date

6.8895362E11
Curative
Approved
8307
ZITHROMAX

Approved Use

Azithromycin Tablets, USP are indicated for the treatment of patients with mild to moderate infections (pneumonia: see WARNINGS ) caused by susceptible strains of the designated microorganisms in the specific conditions listed below. As recommended dosages, durations of therapy and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific dosing recommendations. Adults Acute bacterial exacerbations of chronic obstructive pulmonary disease due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Acute bacterial sinusitis due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. NOTE: Azithromycin should not be used in patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, elderly or debilitated patients, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Uncomplicated skin and skin structure infections due to Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus agalactiae. Abscesses usually require surgical drainage. Urethritis and cervicitis due to Chlamydia trachomatis or Neisseria gonorrhoeae. Genital ulcer disease in men due to Haemophilus ducreyi (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. Azithromycin, at the recommended dose, should not be relied upon to treat syphilis. Antimicrobial agents used in high doses for short periods of time to treat non-gonococcal urethritis may mask or delay the symptoms of incubating syphilis. All patients with sexually-transmitted urethritis or cervicitis should have a serologic test for syphilis and appropriate cultures for gonorrhea performed at the time of diagnosis. Appropriate antimicrobial therapy and follow-up tests for these diseases should be initiated if infection is confirmed. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly. To reduce the development of drug-resistant bacteria and maintain the effectiveness of azithromycin and other antibacterial drugs, azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Pediatric Patients: (See PRECAUTIONS—Pediatric Use and CLINICAL STUDIES IN PEDIATRIC PATIENTS .) Acute otitis media caused by Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Azithromycin should not be used in pediatric patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly.

Launch Date

6.8895362E11
Curative
Approved
8307
ZITHROMAX

Approved Use

Azithromycin Tablets, USP are indicated for the treatment of patients with mild to moderate infections (pneumonia: see WARNINGS ) caused by susceptible strains of the designated microorganisms in the specific conditions listed below. As recommended dosages, durations of therapy and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific dosing recommendations. Adults Acute bacterial exacerbations of chronic obstructive pulmonary disease due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Acute bacterial sinusitis due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. NOTE: Azithromycin should not be used in patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, elderly or debilitated patients, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Uncomplicated skin and skin structure infections due to Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus agalactiae. Abscesses usually require surgical drainage. Urethritis and cervicitis due to Chlamydia trachomatis or Neisseria gonorrhoeae. Genital ulcer disease in men due to Haemophilus ducreyi (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. Azithromycin, at the recommended dose, should not be relied upon to treat syphilis. Antimicrobial agents used in high doses for short periods of time to treat non-gonococcal urethritis may mask or delay the symptoms of incubating syphilis. All patients with sexually-transmitted urethritis or cervicitis should have a serologic test for syphilis and appropriate cultures for gonorrhea performed at the time of diagnosis. Appropriate antimicrobial therapy and follow-up tests for these diseases should be initiated if infection is confirmed. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly. To reduce the development of drug-resistant bacteria and maintain the effectiveness of azithromycin and other antibacterial drugs, azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Pediatric Patients: (See PRECAUTIONS—Pediatric Use and CLINICAL STUDIES IN PEDIATRIC PATIENTS .) Acute otitis media caused by Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Azithromycin should not be used in pediatric patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly.

Launch Date

6.8895362E11
Curative
Approved
8307
ZITHROMAX

Approved Use

Azithromycin Tablets, USP are indicated for the treatment of patients with mild to moderate infections (pneumonia: see WARNINGS ) caused by susceptible strains of the designated microorganisms in the specific conditions listed below. As recommended dosages, durations of therapy and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific dosing recommendations. Adults Acute bacterial exacerbations of chronic obstructive pulmonary disease due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Acute bacterial sinusitis due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. NOTE: Azithromycin should not be used in patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, elderly or debilitated patients, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Uncomplicated skin and skin structure infections due to Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus agalactiae. Abscesses usually require surgical drainage. Urethritis and cervicitis due to Chlamydia trachomatis or Neisseria gonorrhoeae. Genital ulcer disease in men due to Haemophilus ducreyi (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. Azithromycin, at the recommended dose, should not be relied upon to treat syphilis. Antimicrobial agents used in high doses for short periods of time to treat non-gonococcal urethritis may mask or delay the symptoms of incubating syphilis. All patients with sexually-transmitted urethritis or cervicitis should have a serologic test for syphilis and appropriate cultures for gonorrhea performed at the time of diagnosis. Appropriate antimicrobial therapy and follow-up tests for these diseases should be initiated if infection is confirmed. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly. To reduce the development of drug-resistant bacteria and maintain the effectiveness of azithromycin and other antibacterial drugs, azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Pediatric Patients: (See PRECAUTIONS—Pediatric Use and CLINICAL STUDIES IN PEDIATRIC PATIENTS .) Acute otitis media caused by Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Azithromycin should not be used in pediatric patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly.

Launch Date

6.8895362E11
Curative
Approved
8307
ZITHROMAX

Approved Use

Azithromycin Tablets, USP are indicated for the treatment of patients with mild to moderate infections (pneumonia: see WARNINGS ) caused by susceptible strains of the designated microorganisms in the specific conditions listed below. As recommended dosages, durations of therapy and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific dosing recommendations. Adults Acute bacterial exacerbations of chronic obstructive pulmonary disease due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Acute bacterial sinusitis due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. NOTE: Azithromycin should not be used in patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, elderly or debilitated patients, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Uncomplicated skin and skin structure infections due to Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus agalactiae. Abscesses usually require surgical drainage. Urethritis and cervicitis due to Chlamydia trachomatis or Neisseria gonorrhoeae. Genital ulcer disease in men due to Haemophilus ducreyi (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. Azithromycin, at the recommended dose, should not be relied upon to treat syphilis. Antimicrobial agents used in high doses for short periods of time to treat non-gonococcal urethritis may mask or delay the symptoms of incubating syphilis. All patients with sexually-transmitted urethritis or cervicitis should have a serologic test for syphilis and appropriate cultures for gonorrhea performed at the time of diagnosis. Appropriate antimicrobial therapy and follow-up tests for these diseases should be initiated if infection is confirmed. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly. To reduce the development of drug-resistant bacteria and maintain the effectiveness of azithromycin and other antibacterial drugs, azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Pediatric Patients: (See PRECAUTIONS—Pediatric Use and CLINICAL STUDIES IN PEDIATRIC PATIENTS .) Acute otitis media caused by Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Azithromycin should not be used in pediatric patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly.

Launch Date

6.8895362E11
Curative
Approved
8307
ZITHROMAX

Approved Use

Azithromycin Tablets, USP are indicated for the treatment of patients with mild to moderate infections (pneumonia: see WARNINGS ) caused by susceptible strains of the designated microorganisms in the specific conditions listed below. As recommended dosages, durations of therapy and applicable patient populations vary among these infections, please see DOSAGE AND ADMINISTRATION for specific dosing recommendations. Adults Acute bacterial exacerbations of chronic obstructive pulmonary disease due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Acute bacterial sinusitis due to Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. NOTE: Azithromycin should not be used in patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, elderly or debilitated patients, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Uncomplicated skin and skin structure infections due to Staphylococcus aureus, Streptococcus pyogenes, or Streptococcus agalactiae. Abscesses usually require surgical drainage. Urethritis and cervicitis due to Chlamydia trachomatis or Neisseria gonorrhoeae. Genital ulcer disease in men due to Haemophilus ducreyi (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. Azithromycin, at the recommended dose, should not be relied upon to treat syphilis. Antimicrobial agents used in high doses for short periods of time to treat non-gonococcal urethritis may mask or delay the symptoms of incubating syphilis. All patients with sexually-transmitted urethritis or cervicitis should have a serologic test for syphilis and appropriate cultures for gonorrhea performed at the time of diagnosis. Appropriate antimicrobial therapy and follow-up tests for these diseases should be initiated if infection is confirmed. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly. To reduce the development of drug-resistant bacteria and maintain the effectiveness of azithromycin and other antibacterial drugs, azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Pediatric Patients: (See PRECAUTIONS—Pediatric Use and CLINICAL STUDIES IN PEDIATRIC PATIENTS .) Acute otitis media caused by Haemophilus influenzae, Moraxella catarrhalis or Streptococcus pneumoniae. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) Community-acquired pneumonia due to Chlamydophila pneumoniae, Haemophilus influenzae, Mycoplasma pneumoniae or Streptococcus pneumoniae in patients appropriate for oral therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Azithromycin should not be used in pediatric patients with pneumonia who are judged to be inappropriate for oral therapy because of moderate to severe illness or risk factors such as any of the following: patients with cystic fibrosis, patients with nosocomially acquired infections, patients with known or suspected bacteremia, patients requiring hospitalization, or patients with significant underlying health problems that may compromise their ability to respond to their illness (including immunodeficiency or functional asplenia). Pharyngitis/tonsillitis caused by Streptococcus pyogenes as an alternative to first-line therapy in individuals who cannot use first-line therapy. (For specific dosage recommendation, see DOSAGE AND ADMINISTRATION .) NOTE: Penicillin by the intramuscular route is the usual drug of choice in the treatment of Streptococcus pyogenes infection and the prophylaxis of rheumatic fever. Azithromycin is often effective in the eradication of susceptible strains of Streptococcus pyogenes from the nasopharynx. Because some strains are resistant to azithromycin, susceptibility tests should be performed when patients are treated with azithromycin. Data establishing efficacy of azithromycin in subsequent prevention of rheumatic fever are not available. Appropriate culture and susceptibility tests should be performed before treatment to determine the causative organism and its susceptibility to azithromycin. Therapy with azithromycin may be initiated before results of these tests are known; once the results become available, antimicrobial therapy should be adjusted accordingly.

Launch Date

6.8895362E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.39 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18252692/
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.94 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18252692/
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.54 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg 1 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.5 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.94 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18252692/
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
10 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18252692/
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
17.4 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg 1 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.3 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
71.8 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg 1 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
71%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg 1 times / day multiple, oral
dose: 500 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AZITHROMYCIN ANHYDROUS serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
71%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050710s44-050711s41-050784s28lbl.pdf
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZITHROMYCIN ANHYDROUS unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
2 g 1 times / day single, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: single
Dose: 2 g, 1 times / day
Sources:
https://www.nejm.org/doi/full/10.1056/nejm199209243271304
unhealthy, 25.2 (16-50)
n = 237
Health Status: unhealthy
Condition: urethral or endocervical infections with Chlamydia trachomatis.
Age Group: 25.2 (16-50)
Sex: M+F
Population Size: 237
Sources:
https://www.nejm.org/doi/full/10.1056/nejm199209243271304
Sources:
https://www.nejm.org/doi/full/10.1056/nejm199209243271304
0.5 g 1 times / day single, intravenous
Recommended
Dose: 0.5 g, 1 times / day
Route: intravenous
Route: single
Dose: 0.5 g, 1 times / day
Sources:
https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(97)90098-9
healthy, 42 (25-56)
n = 12
Health Status: healthy
Age Group: 42 (25-56)
Population Size: 12
Sources:
https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(97)90098-9
Sources:
https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(97)90098-9
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
unhealthy, adult
n = 301
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
Disc. AE: Sinusitis, Throat infection...
AEs leading to
discontinuation/dose reduction:
Sinusitis
Throat infection
Upper respiratory tract infection
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
unhealthy, adult
n = 333
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 333
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
Disc. AE: Iritis, Conjunctivitis bacterial...
AEs leading to
discontinuation/dose reduction:
Iritis
Conjunctivitis bacterial
Conjunctivitis
Irritability
Herpes zoster
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
0.5 g 2 times / day multiple, intravenous
Recommended
Dose: 0.5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.5 g, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
unknown, adult
Health Status: unknown
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
Other AEs: Angioedema, Anaphylaxis...
Other AEs:
Angioedema
Anaphylaxis
Stevens Johnson syndrome
Toxic epidermal necrolysis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Sinusitis Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
unhealthy, adult
n = 301
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
Throat infection Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
unhealthy, adult
n = 301
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
Upper respiratory tract infection Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
unhealthy, adult
n = 301
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 003
Conjunctivitis bacterial Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
unhealthy, adult
n = 333
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 333
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
Conjunctivitis Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
unhealthy, adult
n = 333
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 333
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
Herpes zoster Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
unhealthy, adult
n = 333
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 333
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
Iritis Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
unhealthy, adult
n = 333
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 333
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
Irritability Disc. AE
1 % 2 times / day multiple, ophthalmic
Recommended
Dose: 1 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
unhealthy, adult
n = 333
Health Status: unhealthy
Condition: bacterial conjunctivitis
Age Group: adult
Sex: M+F
Population Size: 333
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/050810s000_MedR.pdf
Page: Study 004
Anaphylaxis
0.5 g 2 times / day multiple, intravenous
Recommended
Dose: 0.5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.5 g, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
unknown, adult
Health Status: unknown
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
Angioedema
0.5 g 2 times / day multiple, intravenous
Recommended
Dose: 0.5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.5 g, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
unknown, adult
Health Status: unknown
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
Stevens Johnson syndrome
0.5 g 2 times / day multiple, intravenous
Recommended
Dose: 0.5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.5 g, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
unknown, adult
Health Status: unknown
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
Toxic epidermal necrolysis
0.5 g 2 times / day multiple, intravenous
Recommended
Dose: 0.5 g, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.5 g, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
unknown, adult
Health Status: unknown
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050809lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1570

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
584

OAT2
144

OAT3
625

OAT4
145

OATP1A2
34

OATP1B1
770

OATP1B3
691

OATP2B1
121

OCT1
498

OCT2
630
CYP
252

UGT
183

P-gp
1491

MRP2
196
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT2
146
 no
OAT4
145
 no
OATP1A2
34
 no
OATP1B3
700
 no
OCT1
513
 no
OCT2
631
 no
OAT1
588
 yes
OAT3
627
 yes
OATP1B1
785
 yes
OATP2B1
124
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
252
 no
UGT
183
 no
MRP2
196
 yes
P-gp
1491
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1603
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0036XM
A2B Chem
AB48154
AK Scientific
2245AH
AK Scientific
G333
AbovChem LLC
HY-17506
AbovChem LLC
HY-17506A
Angene
AGN-PC-0UPTKE
ApexBio Technology
B1398
ApexBio Technology
B1669
AstaTech
44144
AstaTech
N46072
Axon MedChem
2042
BOC Sciences
117772-70-0
BOC Sciences
83905-01-5
Bide Pharmatech
BD22803
BioSynth
A-9940
BioSynth
Q-200666
Bosche Scientific
A3599
Capot Chemical
35619
Cayman Chemical
15004
Chem Scene
CS-2308
Compound Cloud
23725077
Compound Cloud
441190
Compound Cloud
55185
Enamine
EN300-124208
Fluorochem
210715
Fluorochem
41410
Hangzhou APIChem Technology
AC-093
Hangzhou APIChem Technology
AC-16014
Hangzhou Yuhao Chemical Technology
CJ2083
Hangzhou Yuhao Chemical Technology
LT6959
IBScreen
BB_NC-01452
IBScreen
Bio-0676
KeyOrganics
AS-13638
KeyOrganics
AS-75349
KeyOrganics
FS-5409
MedChem Express
HY-17506
MolPort
MolPort-000-703-093
MolPort
MolPort-002-507-426
MolPort
MolPort-006-069-361
MolPort
MolPort-035-395-771
MolPort
MolPort-042-676-353
Molnova
M10602
Molnova
M16114
Pharmeks
PHAR008664
Pharmeks
PHBB_NC-01335
Ryan Scientific
101-94027
Ryan Scientific
107-57803
Ryan Scientific
Oseltamivir_phosphate
Selleck Chemicals
S4147
Sigma Aldrich
PZ0007
Sigma Aldrich
Y0000306
Sigma Aldrich
Y0000637
Sigma Aldrich
Y0000637|SIAL
Sigma Aldrich
Y0000641
TargetMol
T1419
TargetMol
T6401
Tocris
3771
Toronto Research Chemicals
A927000
W&J PharmaChem
50C547052
ZINC
ZINC000085537026
http://zinc15.docking.org/substances/ZINC000085537026
eMolecules
170737143
eMolecules
261435398
eMolecules
45919070
eMolecules
56748885
eMolecules
6842676
eNovation Chemicals
D625343
mcule
MCULE-4827019524
mcule
MCULE-8817893418
PubMed

PubMed

TitleDatePubMed
Evaluation of the efficacy of atovaquone alone or in combination with azithromycin against acute murine toxoplasmosis.
2000 Apr
Irreversible sensorineural hearing loss as a result of azithromycin ototoxicity. A case report.
2000 Apr
Activity of nitazoxanide alone and in combination with azithromycin and rifabutin against Cryptosporidium parvum in cell culture.
2000 Apr
Pharyngeal colonization prevalence rates for Streptococcus pyogenes and Streptococcus pneumoniae in a respiratory chemoprophylaxis intervention study using azithromycin.
2000 Jan
Apoptosis, oxidative metabolism and interleukin-8 production in human neutrophils exposed to azithromycin: effects of Streptococcus pneumoniae.
2000 Jul
Clinical efficacy of intravenous followed by oral azithromycin monotherapy in hospitalized patients with community-acquired pneumonia. The Azithromycin Intravenous Clinical Trials Group.
2000 Jul
Comparison of azithromycin and doxycycline in the treatment of erythema migrans.
2000 May-Jun
Breakthrough pneumococcal bacteremia in patients being treated with azithromycin and clarithromycin.
2000 Oct
Potentially fatal interaction between azithromycin and disopyramide.
2000 Sep
Antibiotic prophylaxis for intrauterine contraceptive device insertion.
2001
Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens.
2001
Comparison of two azithromycin distribution strategies for controlling trachoma in Nepal.
2001
[Skin eruptions due to azithromycin (Azadose-Zithromax) and infectious mononucleosis].
2001 Apr
Comparative efficacy of new investigational agents against Helicobacter pylori.
2001 Apr
Severe babesiosis in Long Island: review of 34 cases and their complications.
2001 Apr 15
Comparison of amoxicillin and azithromycin in the prevention of recurrent acute otitis media.
2001 Apr 6
Oligella ureolytica in blood culture: contaminant or infection?
2001 Feb
[Subacute infectious endocarditis due to the agent of cat scratch fever: Bartonella henselae].
2001 Feb
Treatment of cat-scratch disease.
2001 Feb
New approaches to the treatment of group A streptococcal pharyngitis.
2001 Feb
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.
2001 Feb
Rhodococcus equi and cytomegalovirus pneumonia in a renal transplant patient: diagnosis by fine-needle aspiration biopsy.
2001 Feb
Azithromycin and gentamicin therapy for the treatment of humans with brucellosis.
2001 Feb 1
Evaluation of iron-phosphate as a source of internal lake phosphorus loadings.
2001 Feb 5
Azithromycin monthly pulse vs daily doxycycline in the treatment of acne vulgaris.
2001 Jan
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.
2001 Jan
Compliance issues related to the selection of antibiotic suspensions for children.
2001 Jan
Activity of buforin II alone and in combination with azithromycin and minocycline against Cryptosporidium parvum in cell culture.
2001 Jan
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
In vitro activity of ketolides HMR 3004 and HMR 3647 and seven other antimicrobial agents against Corynebacterium diphtheriae.
2001 Jan
Resolution of cyclosporine-induced gingival hyperplasia resistant to azithromycin by switching to tacrolimus.
2001 Jan
Activity of moxifloxacin by itself and in combination with ethambutol, rifabutin, and azithromycin in vitro and in vivo against Mycobacterium avium.
2001 Jan
Effect of azithromycin on murine arteriosclerosis exacerbated by Chlamydia pneumoniae.
2001 Jan 15
Chlamydia pneumoniae infection in circulating human monocytes is refractory to antibiotic treatment.
2001 Jan 23
Buccal adherence of Pseudomonas aeruginosa in patients with cystic fibrosis under long-term therapy with azithromycin.
2001 Jan-Feb
Malaria chemoprophylaxis in the age of drug resistance. I. Currently recommended drug regimens.
2001 Jul 15
A randomized controlled trial comparing amoxicillin and azithromycin for the treatment of Chlamydia trachomatis in pregnancy.
2001 Jun
Susceptibility of Canadian isolates of Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pneumoniae to oral antimicrobial agents.
2001 Jun
Persistently positive culture results in a patient with community-acquired pneumonia due to Legionella pneumophila.
2001 Jun 1
Macrolide therapy of group A streptococcal pharyngitis: 10 days of macrolide therapy (clarithromycin) is more effective in streptococcal eradication than 5 days (azithromycin).
2001 Jun 15
A family cluster of Chlamydia trachomatis infection.
2001 Jun 16
Postantibiotic suppression effect of macrolides on the expression of flagellin in Pseudomonas aeruginosa and Proteus mirabilis.
2001 Mar
Pharmacokinetic and safety profile of desloratadine and fexofenadine when coadministered with azithromycin: a randomized, placebo-controlled, parallel-group study.
2001 Mar
The activity of antibiotics against Legionella pneumophila: in vitro and in vivo studies.
2001 Mar
Dose-escalation, phase I/II study of azithromycin and pyrimethamine for the treatment of toxoplasmic encephalitis in AIDS.
2001 Mar 30
Treatment outcomes in acute exacerbations of chronic bronchitis: comparison of macrolides and moxifloxacin from the patient perspective.
2001 Mar-Apr
[Pharmacological and pharmacokinetic properties of azithromycin (Zithromac), a novel 15-membered ring macrolide antibacterial agent].
2001 May
The effects of intravenous doxycycline therapy for rheumatoid arthritis: a randomized, double-blind, placebo-controlled trial.
2001 May
Inoculation of two genotypes of Hemobartonella felis (California and Ohio variants) to induce infection in cats and the response to treatment with azithromycin.
2001 May
[Chemoprophylaxis of meningococcal disease with azithromycin and ciprofloxacin].
2001 May
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Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Fri Dec 16 18:32:58 UTC 2022
Edited
by admin
on Fri Dec 16 18:32:58 UTC 2022
Record UNII
5FD1131I7S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZITHROMYCIN DIHYDRATE
MI   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
AZITHROMYCIN [MART.]
Common Name English
AZITHROMYCIN DIHYDRATE [USP MONOGRAPH]
Common Name English
ZMAX
Common Name English
N-METHYL-11-AZA-10-DEOXO-10-DIHYDROERYTHROMYCIN A DIHYDRATE
Common Name English
Azithromycin dihydrate [WHO-DD]
Common Name English
ZITHROMAX
Brand Name English
AZITHROMYCIN HYDRATE [JAN]
Common Name English
AZITHROMYCIN HYDRATE
JAN  
Common Name English
AZITHROMYCIN DIHYDRATE [EP MONOGRAPH]
Common Name English
AZITHROMYCIN DIHYDRATE [VANDF]
Common Name English
AZITHROMYCIN DIHYDRATE [ORANGE BOOK]
Common Name English
AZITHROMYCIN DIHYDRATE [MI]
Common Name English
AZITHROMYCIN (AS DIHYDRATE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
Code System Code Type Description
MERCK INDEX
M2177
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY Merck Index
FDA UNII
5FD1131I7S
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
EVMPD
SUB20599
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
ChEMBL
CHEMBL529
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
RXCUI
253155
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY RxNorm
EPA CompTox
DTXSID80922539
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
PUBCHEM
3033819
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
EVMPD
SUB16399MIG
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
CHEBI
2955
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
CAS
117772-70-0
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
NCI_THESAURUS
C76214
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
DRUG BANK
DBSALT000882
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
DAILYMED
5FD1131I7S
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
RS_ITEM_NUM
1046056
Created by admin on Fri Dec 16 18:32:58 UTC 2022 , Edited by admin on Fri Dec 16 18:32:58 UTC 2022
PRIMARY
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Structure of AZITHROMYCIN DIHYDRATE
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Structure of AZITHROMYCIN DIHYDRATE
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Structure of N'-(DESMETHYL)AZITHROMYCIN
IMPURITY -> PARENT
For the calculation of content, multiply the peak area by 0.3
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Structure of AZITHROMYCIN C
IMPURITY -> PARENT
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Structure of 2-DESETHYL-2-PROPYLAZITHROMYCIN
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IMPURITY -> PARENT
For the calculation of content, multiply the peak area 0.6
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EP
Structure of AZITHROMYCIN C
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of AZITHROMYCIN B
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of AZITHROMYCIN 3'- N-OXIDE
IMPURITY -> PARENT
For the calculation of content, multiply the peak area by 2.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 3'-DE(DIMETHYLAMINO)-3'-OXOAZITHROMYCIN
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Unidentified
Structure of 2-DESETHYL-2-PROPYLAZITHROMYCIN
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Structure of 3'-N-DEMETHYL-3'-N-((4-METHYLPHENYL)SULFONYL)AZITHROMYCIN
IMPURITY -> PARENT
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Structure of 3'-N-((4-(ACETYLAMINO)PHENYL)SULFONYL)-3'-N-DEMETHYLAZITHROMYCIN
IMPURITY -> PARENT
For the calculation of content, multiply the peak area by 0.1
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Structure of 3'-N-DEMETHYL-3'-N-((4-METHYLPHENYL)SULFONYL)AZITHROMYCIN
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For the calculation of content, multiply the peak area by 0.2
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sum of impurities D and J: not more than 0.5 percent peak area
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Related Record Type Details
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