General
Preferred name
AZITHROMYCIN
Synonyms
CP-62993 dihydrate ()
Azithromycin Dihydrate ()
Zithromax ()
CP 62993 ()
XZ-450 ()
Azithromycin (Zithromax) ()
AZITHROMYCIN ANHYDROUS ()
Sunamed ()
Azithromycin (hydrate) ()
Azithromycin hydrate ()
AZITHROMYCIN MONOHYDRATE ()
Azithromycin-d3 ()
Clamelle ()
Azitromicina ()
XZ 405 ()
Azyter ()
Aziwin ()
XZ 450 ()
Azithromycin, unspecified form ()
Hemomycin ()
Azithrocin ()
Sumamed ()
Zythromax ()
Azasite ()
Durasite ()
Azithromycine ()
Trozocina ()
CP-62993 ()
Zithromac ()
Aruzilina ()
Azithromycin (as dihydrate) ()
Macrozit ()
CP-62,993 ()
Xithrone ()
NSC-758625 ()
Azithromycin, unspecified ()
Anhydrous azithromycin ()
Aziromycin ()
Azithromycin-13C-d3 ()
P&D ID
PD000892
CAS
83905-01-5
121470-24-4
117772-70-0
163921-65-1
2750534-82-6
Tags
available
drug
drug candidate
Approved by
PMDA
FDA
First approval
1991
Drug indication
urethritis
Syphilis infection
Drug Status
approved
investigational
Max Phase
2.0
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
HALF-LIFE Terminal elimination half-life: 68 hours [FDA label]
PHARMACODYNAMICS Macrolides stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections [A174175]. Azithromycin has additional immunomodulatory effects and has been used in chronic respiratory inflammatory diseases for this purpose [A174172].
INDICATION Azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria in order to prevent the development antimicrobial resistance and maintain the efficacy of azithromycin [FDA label]. Azithromycin is indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the microorganisms listed in the specific conditions below. Recommended dosages, duration of therapy and considerations for various patient populations may vary among these infections. Refer to the FDA label and "Indications" section of this drug entry for detailed information [FDA label]. **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 Pharyngitis/tonsillitis caused by _Streptococcus pyogenes_ as an alternative to first-line therapy in individuals who cannot use first-line therapy. 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. **Pediatric Patients** Acute otitis media caused by _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. Pharyngitis/tonsillitis caused by _Streptococcus pyogenes_ as an alternative to first-line therapy in individuals who cannot use first-line therapy.
ROE Biliary excretion of azithromycin, primarily as unchanged drug, is a major route of elimination. Over a 1 week period, approximately 6% of the administered dose is found as unchanged drug in urine [FDA label].
TOXICITY **Rat Oral LD50**: >2000 mk/kg [MSDS] Possible major adverse effects include cardiovascular arrhythmias and hearing loss. Macrolide resistance is also an ongoing issue [A174172]. Hepatotoxicity has been since in rare cases [A174175]. **A note on the risk of liver toxicity**: Due to the act that azithromycin is mainly eliminated by the liver, caution should be observed when azithromycin is given to patients with decreased hepatic function [FDA label]. **A note on potential renal toxicity**: Because limited data in patients with renal GFR <10 mL/min, caution should be exercised when prescribing azithromycin to these patients [FDA label]. **Use in Pregnancy**: This drug is categorized as a pregnancy category B drug. Reproduction studies have been done in rats and mice at doses up to moderately maternally toxic doses (for example, 200 mg/kg/day). These doses, based on a mg/m2 basis, are approximately 4 and 2 times, respectively, the human daily dose of 500 mg. In the animal studies, no harmful effects to the fetus due to azithromycin were observed. There are, at this time, no conclusive and well-controlled studies that have been done in pregnant women. Because animal reproduction studies do not always predict human response, azithromycin should be used during pregnancy only if clearly needed [FDA label]. **Nursing Mothers**: It is unknown at this time whether azithromycin is excreted in human milk. Because many other drugs are excreted in human milk, caution should be observed when azithromycin is given to a nursing woman [FDA label]. **Carcinogenesis, Mutagenesis, Impairment of Fertility**: Long-term studies in animals have not been performed to study carcinogenic potential. Azithromycin has demonstrated no potential to be mutagenic in standard laboratory tests. No evidence of negative effects on fertility due to azithromycin was found [FDA label].
METABOLISM In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed [FDA label], however, this drug is eliminated by the liver [A174202], [FDA label].
ABSORPTION Bioavailability of azithromycin is 37% following oral administration. Absorption is not affected by food. Macrolide absorption in the intestines is believed to be mediated by P-glycoprotein (ABCB1) efflux transporters, which are known to be encoded by the _ABCB1_ gene [A174175].
PHARMACODYNAMICS Macrolides stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections [A174175].; Azithromycin has additional immunomodulatory effects and has been used in chronic respiratory inflammatory diseases for this purpose [A174172].; ;
MOA In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins [A6505]. Azithromycin binds to the 23S rRNA of the bacterial 50S ribosomal subunit. It stops bacterial protein synthesis by inhibiting the transpeptidation/translocation step of protein synthesis and by inhibiting the assembly of the 50S ribosomal subunit [FDA label], [A14179]. This results in the control of various bacterial infections [A174193], [FDA label]. The strong affinity of macrolides, including azithromycin, for bacterial ribosomes, is consistent with their broad‐spectrum antibacterial activities [A174193].; ; ; Azithromycin is highly stable at a low pH, giving it a longer serum half-life and increasing its concentrations in tissues compared to erythromycin [A174175]. ; ;
INDICATION Azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria in order to prevent the development antimicrobial resistance and maintain the efficacy of azithromycin [FDA label].; ; Azithromycin is indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the microorganisms listed in the specific conditions below. Recommended dosages, duration of therapy and considerations for various patient populations may vary among these infections. Refer to the FDA label and "Indications" section of this drug entry for detailed information [FDA label]. ; ; **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; ; Pharyngitis/tonsillitis caused by _Streptococcus pyogenes_ as an alternative to first-line therapy in individuals who cannot use first-line therapy.; 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.; ; **Pediatric Patients**; ; Acute otitis media caused by _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.; ; Pharyngitis/tonsillitis caused by _Streptococcus pyogenes_ as an alternative to first-line therapy in individuals who cannot use first-line therapy.
DESCPRITION A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.
DESCRIPTION Azithromycin is a macrolide antibacterial with broad-spectrum activity against Gram-positive and atypical bacteria. The compound also has antimalarial activity.
Azithromycin is one of the watch group antibacterials in the the World Health Organization's Model List of Essential Medicines (link provided in the Classification table below).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY. (GtoPdb)
DESCRIPTION Azithromycin is a macrolide antibiotic with broad-spectrum activity against gram-positive and atypical bacteria. The compound also has antimalarial activity and has been investigated as a potential treatment for uncomplicated P. falciparum or P. vivax malaria but does not provide an advantage over current therapies .
Azithromycin is one of the key antibacterials in the WHO 20th Essential Medicines List (2017).
MOA In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins [A6505]. Azithromycin binds to the 23S rRNA of the bacterial 50S ribosomal subunit. It stops bacterial protein synthesis by inhibiting the transpeptidation/translocation step of protein synthesis and by inhibiting the assembly of the 50S ribosomal subunit [FDA label], [A14179]. This results in the control of various bacterial infections [A174193], [FDA label]. The strong affinity of macrolides, including azithromycin, for bacterial ribosomes, is consistent with their broad‐spectrum antibacterial activities [A174193]. Azithromycin is highly stable at a low pH, giving it a longer serum half-life and increasing its concentrations in tissues compared to erythromycin [A174175].
TOXICITY **Rat Oral LD50**: >2000 mk/kg [MSDS]; ; Possible major adverse effects include cardiovascular arrhythmias and hearing loss. Macrolide resistance is also an ongoing issue [A174172]. Hepatotoxicity has been since in rare cases [A174175]. ; ; **A note on the risk of liver toxicity**:; ; Due to the act that azithromycin is mainly eliminated by the liver, caution should be observed when azithromycin is given to patients with decreased hepatic function [FDA label]. ; ; **A note on potential renal toxicity**:; ; Because limited data in patients with renal GFR <10 mL/min, caution should be exercised when prescribing azithromycin to these patients [FDA label].; ; **Use in Pregnancy**:; ; This drug is categorized as a pregnancy category B drug. Reproduction studies have been done in rats and mice at doses up to moderately maternally toxic doses (for example, 200 mg/kg/day). These doses, based on a mg/m2 basis, are approximately 4 and 2 times, respectively, the human daily dose of 500 mg. In the animal studies, no harmful effects to the fetus due to azithromycin were observed. There are, at this time, no conclusive and well-controlled studies that have been done in pregnant women. Because animal reproduction studies do not always predict human response, azithromycin should be used during pregnancy only if clearly needed [FDA label].; ; **Nursing Mothers**: ; ; It is unknown at this time whether azithromycin is excreted in human milk. Because many other drugs are excreted in human milk, caution should be observed when azithromycin is given to a nursing woman [FDA label].; ; **Carcinogenesis, Mutagenesis, Impairment of Fertility**: ; ; Long-term studies in animals have not been performed to study carcinogenic potential. Azithromycin has demonstrated no potential to be mutagenic in standard laboratory tests. No evidence of negative effects on fertility due to azithromycin was found [FDA label].
PRICE 29
DESCRIPTION Azithromycin is a macrolide antibiotic useful for the treatment of a number of bacterial infections.
DESCRIPTION Azithromycin hydrate is a macrolide antibiotic useful for the treatment of a number of bacterial infections.
PRICE 30
DESCRIPTION Antibiotic; inhibits bacterial DNA synthesis (Tocris Bioactive Compound Library)
DESCRIPTION Antibiotic; inhibits 50S ribosomal subunit formation and elongation at transpeptidation (Tocriscreen Plus)
DESCRIPTION Azithromycin is a macrolide antibiotic used to treat a variety of bacterial infections. (Enamine Bioactive Compounds)
DESCRIPTION Azithromycin (CP 62993) is an antibiotic by inhibiting protein synthesis, used for the treatment of bacterial infections. (TargetMol Bioactive Compound Library)
DESCRIPTION Azithromycin hydrate (CP-62993 dihydrate) is a semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis. (TargetMol Bioactive Compound Library)
Cell lines
0
Organisms
14
Compound Sets
31
AdooQ Bioactive Compound Library
A11803
Axon Medchem Screening Library
2042
Cayman Chemical Bioactives
15004
20675
30653
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL529
ChEMBL Drugs
CHEMBL529
CHEMBL1200502
Concise Guide to Pharmacology 2017/18
6510
Concise Guide to Pharmacology 2019/20
6510
Concise Guide to Pharmacology 2021/22
6510
Concise Guide to Pharmacology 2023/24
6510
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB00207
DrugBank Approved Drugs
DB00207
DrugCentral
276
DrugCentral Approved Drugs
276
DrugMAP
DMN4H2O
DrugMAP Approved Drugs
DMN4H2O
Enamine Bioactive Compounds
EBC-14146
EBC-575133
Enamine BioReference Compounds
Guide to Pharmacology
6510
MedChem Express Bioactive Compound Library
HY-17506
HY-17506A
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
J2KLZ20U1M
NIH Clinical Collections (NCC)
Prestwick Chemical Library
ReFrame library
TargetMol Bioactive Compound Library
T6401
T1419
The Spectrum Collection
Tocris Bioactive Compound Library
3771
Tocriscreen Plus
3771
External IDs
156
Properties
(calculated by RDKit )
Molecular Weight
748.51
Hydrogen Bond Acceptors
14
Hydrogen Bond Donors
5
Rotatable Bonds
7
Ring Count
3
Aromatic Ring Count
0
cLogP
1.9
TPSA
180.08
Fraction CSP3
0.97
Chiral centers
18.0
Largest ring
15.0
QED
0.24
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
Cell Biology
MOA
bacterial ribosome inhibitor
Antibacterial
bacterial 50S ribosomal subunit inhibitor
Target
Bacterial 70S ribosome
MLNR
antibiotic
Bacterial
Parasite
23S rRNA
50S ribosome
protein synthesis
Primary Target
DNA, RNA and Protein Synthesis
Pathway
Microbiology&virology
Autophagy
Microbiology/virology
Anti-infection
Indication
pelvic inflammatory disease, pneumonia
Biosynthetic Origin
Polyketide, Carbohydrate (Aminoglycoside)
Therapeutic Class
Antimicrobial
Source data