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Accession Number
DB00207  (APRD00397)
Small Molecule

Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration 3. It was initially approved by the FDA in 1991 4.

It is primarily used for the treatment of respiratory, enteric and genitourinary infections and may be used instead of other macrolides for some sexually transmitted and enteric infections. It is structurally related to erythromycin 2.

Azithromycin [9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin] is a part of the azalide subclass of macrolides, and contains a 15-membered ring, with a methyl-substituted nitrogen instead of a carbonyl group at the 9a position on the aglycone ring, which allows for the prevention of its metabolism. This differentiates azithromycin from other types of macrolides 4.

  • Azithromycin
  • Azithromycine
  • Azithromycinum
  • Azitromicina
External IDs
CP 62993 / CP-62,993 / CP-62993 / XZ 405 / XZ 450 / XZ-450
Product Ingredients
IngredientUNIICASInChI Key
Azithromycin dihydrate5FD1131I7S117772-70-0SRMPHJKQVUDLQE-KUJJYQHYSA-N
Azithromycin monohydrateJTE4MNN1MD121470-24-4HQUPLSLYZHKKQT-WVVFQGGUSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act AzithromycinTabletOralActavis Pharma Company2005-11-022019-06-24Canada
Act AzithromycinTabletOralActavis Pharma Company2005-11-022018-06-12Canada
AzaSITESolution1 %OphthalmicInspire Pharmaceuticals, Inc.Not applicableNot applicableCanada
AzaSITESolution / drops10 mg/1mLOphthalmicAkorn2014-05-14Not applicableUs
AzaSITESolution1 %OphthalmicInsite Vision IncorporatedNot applicableNot applicableCanada
AzaSiteSolution10 mg/1mLOphthalmicInspire Pharmaceuticals, Inc.2007-07-162015-08-31Us
AzithromycinPowder, for suspension100 mgOralPharmascience Inc2006-04-19Not applicableCanada
AzithromycinTablet250 mgOralSanis Health Inc2010-02-01Not applicableCanada
AzithromycinPowder, for suspension1 g/1OralGreenstone LLC1999-02-12Not applicableUs
AzithromycinPowder, for suspension1 g/1OralPhysicians Total Care, Inc.2008-09-08Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ag-azithromycinTabletOralAngita Pharma Inc.2018-09-26Not applicableCanada
Ag-azithromycinTabletOralAngita Pharma Inc.2018-09-26Not applicableCanada
Apo-azithromycinTabletOralApotex Corporation2005-11-02Not applicableCanada
Apo-azithromycin ZTabletOralApotex Corporation2014-03-06Not applicableCanada
Auro-azithromycinPowder, for suspensionOralAuro Pharma Inc2019-10-30Not applicableCanada
Auro-azithromycinPowder, for suspensionOralAuro Pharma Inc2019-10-30Not applicableCanada
Ava-azithromycinTabletOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinPowder, for suspensionOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinPowder, for suspensionOralAvanstra Inc2011-09-192014-08-21Canada
AzithromycinPowder, for suspension200 mg/5mLOralLake Erie Medical DBA Quality Care Products LLC1995-10-19Not applicableUs
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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International/Other Brands
Azenil / Azibiot / Azifast / Azigram / Azimakrol / Azin / Azithrocin / Azitromax / Azitromin / Aztrin / Hemomycin / Misultina / Penalox / Sumamed / Vinzam / Zifin / Zitrocin / Zitrotek
CAS number
Average: 748.9845
Monoisotopic: 748.508525778
Chemical Formula
InChI Key



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 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 Label.


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.

Associated Conditions

Macrolides stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections 4. Azithromycin has additional immunomodulatory effects and has been used in chronic respiratory inflammatory diseases for this purpose 3.

Mechanism of action

In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins 6. 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 Label, 5. This results in the control of various bacterial infections 7, Label. The strong affinity of macrolides, including azithromycin, for bacterial ribosomes, is consistent with their broad‐spectrum antibacterial activities 7.

Azithromycin is highly stable at a low pH, giving it a longer serum half-life and increasing its concentrations in tissues compared to erythromycin 4.

A23S ribosomal RNA
Enteric bacteria and other eubacteria
UProtein-arginine deiminase type-4
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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 4.

Volume of distribution

After oral administration, azithromycin is widely distributed in tissues with an apparent steady-state volume of distribution of 31.1 L/kg Label. Significantly greater azithromycin concentrations have been measured in the tissues rather than in plasma or serum Label, 3. The lung, tonsils and prostate are organs have shown a particularly high rate of azithromycin uptake 3.

This drug is concentrated within macrophages and polymorphonucleocytes, allowing for effective activity against Chlamydia trachomatis 4. In addition, azithromycin is found to be concentrated in phagocytes and fibroblasts, shown by in vitro incubation techniques. In vivo studies demonstrate that concentration in phagocytes may contribute to azithromycin distribution to inflamed tissues Label.

Protein binding

The serum protein binding of azithromycin varies in humans, decreasing from 51% at 0.02 g/mL to 7% at 2 g/mL Label.


In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed Label, however, this drug is eliminated by the liver 8, Label.

Route of elimination

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 Label.

Half life

Terminal elimination half-life: 68 hours Label


Mean apparent plasma cl=630 mL/min (following single 500 mg oral and i.v. dose) Label


Rat Oral LD50: >2000 mk/kg MSDS

Possible major adverse effects include cardiovascular arrhythmias and hearing loss. Macrolide resistance is also an ongoing issue 3. Hepatotoxicity has been since in rare cases 4.

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 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 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 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 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 Label.

Affected organisms
  • Humans and other mammals
Azithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
(R)-warfarinThe risk or severity of adverse effects can be increased when Azithromycin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Azithromycin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Azithromycin is combined with 4-hydroxycoumarin.
6-Deoxyerythronolide BThe metabolism of Azithromycin can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecinThe metabolism of Azithromycin can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Azithromycin.
AbataceptThe metabolism of Azithromycin can be increased when combined with Abatacept.
AbciximabThe risk or severity of adverse effects can be increased when Azithromycin is combined with Abciximab.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Azithromycin.
AbexinostatThe risk or severity of QTc prolongation can be increased when Azithromycin is combined with Abexinostat.
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Food Interactions
  • Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.


Synthesis Reference

William Heggie, Zita Maria De Mouro Vaz Azevedo Mendes, "Process for the preparation of azithromycin." U.S. Patent US6013778, issued November, 1994.

General References
  1. Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [PubMed:17051490]
  2. Peters DH, Friedel HA, McTavish D: Azithromycin. A review of its antimicrobial activity, pharmacokinetic properties and clinical efficacy. Drugs. 1992 Nov;44(5):750-99. doi: 10.2165/00003495-199244050-00007. [PubMed:1280567]
  3. McMullan BJ, Mostaghim M: Prescribing azithromycin. Aust Prescr. 2015 Jun;38(3):87-9. Epub 2015 Jun 1. [PubMed:26648627]
  4. Fohner AE, Sparreboom A, Altman RB, Klein TE: PharmGKB summary: Macrolide antibiotic pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2017 Apr;27(4):164-167. doi: 10.1097/FPC.0000000000000270. [PubMed:28146011]
  5. Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin. Curr Microbiol. 2002 Jun;44(6):418-24. [PubMed:12000992]
  6. Champney WS, Burdine R: Macrolide antibiotics inhibit 50S ribosomal subunit assembly in Bacillus subtilis and Staphylococcus aureus. Antimicrob Agents Chemother. 1995 Sep;39(9):2141-4. [PubMed:8540733]
  7. Dinos GP: The macrolide antibiotic renaissance. Br J Pharmacol. 2017 Sep;174(18):2967-2983. doi: 10.1111/bph.13936. Epub 2017 Aug 10. [PubMed:28664582]
  8. Singlas E: [Clinical pharmacokinetics of azithromycin]. Pathol Biol (Paris). 1995 Jun;43(6):505-11. [PubMed:8539072]
  9. Zithromax FDA label [File]
  10. Azithromycin, Ophthalmic FDA label [File]
  11. Sandoz Azithromycin Canadian Monograph [File]
External Links
Human Metabolome Database
KEGG Compound
PubChem Compound
PubChem Substance
Therapeutic Targets Database
PDBe Ligand
RxList Drug Page Drug Page
ATC Codes
J01RA07 — Azithromycin, fluconazole and secnidazoleS01AA26 — AzithromycinJ01FA10 — Azithromycin
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.12.92 — Other Macrolides
PDB Entries
1m1k / 1nwy / 1yhq / 4v7y / 5igi / 5igv / 5uxc / 5uxd
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Clinical Trials

Clinical Trials
0CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
0Not Yet RecruitingTreatmentAcne Vulgaris1
0RecruitingTreatmentBMI >30 kg/m2 / Induction of Labor Affected Fetus / Newborn1
1CompletedNot AvailableFasting1
1CompletedNot AvailableHealthy Volunteers7
1CompletedNot AvailableProphylaxis of Malaria1
1CompletedBasic ScienceAutoimmune Diseases1
1CompletedBasic ScienceBioequivalence / Bioequivalence Study / Chinese Healthy Subjects Under Fasted Condition / Chinese Healthy Subjects Under Fed Condition1
1CompletedBasic ScienceInflammatory Reaction1
1CompletedBasic SciencePharmacokinetics1
1CompletedBasic SciencePrebiotics / Probiotics / Quorum Sensing / Sepsis1
1CompletedDiagnosticLung Function / Sarcoidosis, Pulmonary1
1CompletedHealth Services ResearchPlasmodium Infections1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) / Plasmodium Infections / Pregnant State1
1CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections2
1CompletedTreatmentBacterial Infections / Ureaplasma1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Toxoplasmosis, Cerebral1
1CompletedTreatmentOcular bacterial infections5
1Not Yet RecruitingPreventionDental Implant Failed1
1RecruitingBasic ScienceHealthy Volunteers / Normal Physiology / Physiological Response to Antibiotics1
1RecruitingTreatmentBacterial Conjunctivitis1
1WithdrawnPreventionAcute Chest Syndrome / Sickle Cell Disorders1
1, 2CompletedDiagnosticSarcoidosis1
1, 2Not Yet RecruitingTreatmentEbola Virus Disease1
1, 2RecruitingDiagnosticIntubation Complications1
1, 2RecruitingPreventionRandomized Controll Trial1
1, 2TerminatedPreventionBacteria Infection / Respiratory Tract Infections (RTI)1
1, 2WithdrawnOtherSickle Cell Disorders1
1, 2WithdrawnPreventionMalaria caused by Plasmodium falciparum1
1, 2WithdrawnTreatmentThyroid Eye Disease1
2Active Not RecruitingTreatmentChildhood Asthma With Acute Exacerbation1
2Active Not RecruitingTreatmentPeriodontitis, Chronic1
2Active Not RecruitingTreatmentUreaplasma Infections1
2CompletedNot AvailableSinusitis1
2CompletedBasic SciencePharmacokinetics1
2CompletedPreventionChronic Lung Disease of Prematurity1
2CompletedTreatmentAcute Otitis Media1
2CompletedTreatmentAsthma in Children1
2CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Pneumocystis Jirovecii Pneumonia1
2CompletedTreatmentBronchiolitis Obliterans (BO)1
2CompletedTreatmentChlamydia Trachomatis Infection1
2CompletedTreatmentChlamydial Infections1
2CompletedTreatmentDisseminated Sclerosis1
2CompletedTreatmentEsophageal Motility Disorders1
2CompletedTreatmentFatty Liver / Insulin Resistance / Liver Dysfunction1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare2
2CompletedTreatmentLymphatic Filariasis / Traumas / Yaws1
2CompletedTreatmentMalaria caused by Plasmodium falciparum2
2CompletedTreatmentObsessive Compulsive Disorder (OCD) / PANS / Pediatric Autoimmune Neuropsychiatric Disorders Associated With Streptococcal Infections1
2CompletedTreatmentPeriodontitis, Chronic1
2CompletedTreatmentPlasmodium Falciparum Malaria1
2CompletedTreatmentPosterior Blepharitis1
2CompletedTreatmentRsv Bronchiolitis1
2CompletedTreatmentSarcoidosis; Antimycobacterial Therapy1
2CompletedTreatmentUncomplicated Falciparum Malaria1
2CompletedTreatmentBacterial blepharitis3
2Not Yet RecruitingTreatmentCrohn's Disease (CD) / Pediatric Crohns Disease1
2Not Yet RecruitingTreatmentGastrointestinal Hemorrhage / Upper Gastrointestinal Hemorrhage1
2RecruitingPreventionCesarean Section; Infection / Endometritis / Wound Infections1
2RecruitingPreventionHuman Immunodeficiency Virus (HIV) / Pregnancy Malaria / Sexually Transmitted Infections (STIs)1
2RecruitingTreatmentChlamydophila Pneumoniae Infections / Coronary Heart Disease (CHD)1
2RecruitingTreatmentChronic Asthma1
2RecruitingTreatmentDiabetes Mellitus / Diet Modification / Endocrine System Diseases / Glucose Metabolism Disorders / Inflammatory Reaction / Insulin Dependent Diabetes / Metabolic Diseases / Type 1 Diabetes Mellitus1
2RecruitingTreatmentPlasmodium Infections1
2RecruitingTreatmentPulmonary Tuberculosis (TB)1
2RecruitingTreatmentSarcoidosis, Pulmonary1
2TerminatedPreventionBronchiectasis / Chronic Bronchitis / Pulmonary Diseases1
2TerminatedPreventionBronchiolitis Obliterans (BO) / Cryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Respiratory Tract Infections (RTI)1
2TerminatedPreventionChronic Obstructive Pulmonary Disease (COPD) / Tracheostomy care1
2TerminatedPreventionPseudomonas Infections / Ventilator-Associated Pneumonia (VAP)1
2TerminatedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
2TerminatedTreatmentMalaria caused by Plasmodium falciparum1
2TerminatedTreatmentPharyngitis / Tonsillitis1
2TerminatedTreatmentPosterior Blepharoconjunctivitis1
2TerminatedTreatmentBacterial blepharitis1
2Unknown StatusTreatmentAcne1
2Unknown StatusTreatmentCystic Fibrosis (CF)1
2Unknown StatusTreatmentPediatric Autoimmune Neuropsychiatric Disorders Associated With Streptococcal Infections1
2Unknown StatusTreatmentPlasmodium Infections1
2WithdrawnTreatmentMeibomian Gland Dysfunction (MGD)1
2, 3Active Not RecruitingTreatmentCognitive Development / Enteric Pathogens / Malnutrition / Stunting1
2, 3Active Not RecruitingTreatmentRespiratory Syncytial Virus (RSV)1
2, 3Active Not RecruitingTreatmentRespiratory Syncytial Virus, Bronchiolitis1
2, 3CompletedScreeningLow Risk of Preterm Delivery1
2, 3CompletedTreatmentMalaria caused by Plasmodium falciparum3
2, 3CompletedTreatmentPlasmodium Falciparum Malaria1
2, 3RecruitingPreventionEnteric Pathogens / Infection caused by Campylobacter fetus / Malnutrition; Protein / Stunting1
2, 3RecruitingTreatmentMycobacterium avium complex infection / Nontuberculous Mycobacterium Infection1
2, 3TerminatedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
2, 3TerminatedTreatmentLeishmaniasis, Cutaneous1
2, 3TerminatedTreatmentMalaria caused by Plasmodium falciparum1
2, 3WithdrawnTreatmentTrachoma1
3Active Not RecruitingPreventionBronchiectasis / Cystic Fibrosis (CF)1
3Active Not RecruitingPreventionMalignant Hematological Diseases1
3Active Not RecruitingPreventionPlasmodium Infections / Pregnancy / Premature Births / Sexually Transmitted Disease (STD)1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)2
3Active Not RecruitingTreatmentNon Cystic Fibrosis Bronchiectasis in Children1
3Active Not RecruitingTreatmentUndifferentiated Febrile Illness1
3Active Not RecruitingTreatmentYaws1
3CompletedPreventionAnemias / Malaria in Pregnancy / Sexually Transmitted Infections (STIs)1
3CompletedPreventionCardiovascular Heart Disease / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction1
3CompletedPreventionPlasmodium Infections / Respiratory Tract Infections (RTI)1
3CompletedTreatmentAbdominal Pain / Diarrhea / Fevers / Vomiting1
3CompletedTreatmentAcute Otitis Media1
3CompletedTreatmentAcute Tracheobronchitis1
3CompletedTreatmentAsthma / Wheezing1
3CompletedTreatmentBacterial Conjunctivitis3
3CompletedTreatmentBronchitis / Chronic Bronchitis1
3CompletedTreatmentChlamydial Infections1
3CompletedTreatmentChronic Bronchitis3
3CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Coughing1
3CompletedTreatmentChronic Lung Diseases / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentCommunity Acquired Pneumonia (CAP)3
3CompletedTreatmentCystic Fibrosis (CF)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Mycoses1
3CompletedTreatmentLymphatic Filariases / Oesophagostomiasis / Scabies / Trachoma / Yaws1
3CompletedTreatmentMaxillary Sinusitis1
3CompletedTreatmentNeglected Tropical Disease / Treponema Infection / Yaws1
3CompletedTreatmentOtitis Media (OM)1
3CompletedTreatmentPelvic Inflammatory Disease (PID)1
3CompletedTreatmentPharyngitis / Tonsillitis1
3CompletedTreatmentPlasmodium Falciparum Infection1
3CompletedTreatmentPlasmodium Infections2
3CompletedTreatmentReactive Arthritis / Reiter's Disease1
3CompletedTreatmentUncomplicated Urogenital Gonorrhea1
3CompletedTreatmentUpper Respiratory Tract Infection1
3CompletedTreatmentBacterial blepharitis2
3Not Yet RecruitingOtherChronic Bronchitis / Chronic, severe Obstructive Pulmonary Disease1
3Not Yet RecruitingPreventionChild Mortality1
3Not Yet RecruitingPreventionMaternal Deaths / Maternal Infections Affecting Fetus or Newborn / Maternal Sepsis During Labor / Neonatal Deaths / Neonatal Sepsis / Puerperal Sepsis1
3Not Yet RecruitingTreatmentSevere Chronic Periodontitis1
3RecruitingDiagnosticPneumonia / Respiratory Tract Infections (RTI) / Tuberculosis Infection1
3RecruitingPreventionBacterial Infections1
3RecruitingPreventionNeonatal Sepsis1
3RecruitingTreatmentChronic Cough (CC)1
3RecruitingTreatmentLung Infection / Mycobacterium avium complex infection1
3RecruitingTreatmentPreterm Premature Rupture of Membranes (PPROM)1
3TerminatedPreventionIntermittent Preventive Treatment In Pregnancy (IPTp)1
3TerminatedTreatmentAcne Vulgaris1
3TerminatedTreatmentAsymptomatic Parasitemia In Pregnancy1
3TerminatedTreatmentBacterial Vaginitis / Cervicitis1
3TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3TerminatedTreatmentOtitis Media, Purulent / Otitis Media, Suppurative1
3Unknown StatusNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentBronchiectasis / Inflammatory Reaction1
3WithdrawnPreventionChronic Lung Disease of Prematurity1
3WithdrawnPreventionPreterm Premature Ruptured Membranes1
3WithdrawnTreatmentBacterial Conjunctivitis / Corneal Inflammation / Eye inflammation / Infection Associated Blepharitis1
3WithdrawnTreatmentCommunity Acquired Pneumonia (CAP)1
4Active Not RecruitingPreventionPremature Births1
4Active Not RecruitingTreatmentCo-Infection / Death / Diarrhea / Malnutrition / Plasmodium Infections / Pneumonia1
4Active Not RecruitingTreatmentCystic Fibrosis (CF)1
4Active Not RecruitingTreatmentYaws1
4CompletedNot AvailableHealthy Volunteers1
4CompletedNot AvailablePregnancy1
4CompletedNot AvailableRespiratory Tract Infections (RTI)1
4CompletedDiagnosticHealthy Volunteers1
4CompletedPreventionBronchiolitis Obliterans Syndrome (BOS) / Lymphocytic Bronchiolitis / Rejection, Transplant / Respiratory Tract Infections (RTI)1
4CompletedPreventionFlu caused by Influenza1
4CompletedPreventionWound Sepsis1
4CompletedSupportive CareBacterial Infections / Cataract Extraction / Eye Infections1
4CompletedSupportive CareBacterial Infections / Eye Infections2
4CompletedTreatmentAcute Otitis Media1
4CompletedTreatmentBacterial Vaginosis (BV)1
4CompletedTreatmentChild's Development1
4CompletedTreatmentChildhood Mortality1
4CompletedTreatmentChlamydia Trachomatis / Human Immunodeficiency Virus (HIV) / Neisseria Gonorrhoeae Infection1
4CompletedTreatmentChlamydia Trachomatis / Trachoma1
4CompletedTreatmentChlamydial Infections / Trachoma3
4CompletedTreatmentChronic Rhinosinusitis / High-risk Patients1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentContact Lens Dry Eye1
4CompletedTreatmentCrohn's Disease (CD)1
4CompletedTreatmentCystic Fibrosis (CF)1
4CompletedTreatmentDisorders Related to Lung Transplantation1
4CompletedTreatmentDry Eye Syndrome (DES)1
4CompletedTreatmentDyspepsia / Helicobacter Pylori / Peptic Ulcer1
4CompletedTreatmentImpetigo / Scabies / Yaws1
4CompletedTreatmentLymphocytic Bronchi(Oli)Tis Post-lung Transplantation1
4CompletedTreatmentUrinary Bladder, Overactive1
4CompletedTreatmentBacterial blepharitis5
4Enrolling by InvitationTreatmentChildhood Mortality1
4Enrolling by InvitationTreatmentCystic Fibrosis (CF)1
4Not Yet RecruitingBasic ScienceMicrobial Colonization1
4Not Yet RecruitingDiagnosticHelminth Infection1
4Not Yet RecruitingPreventionLow Birthweight / Maternal; Malnutrition, Affecting Fetus / Pregnancy and Infectious Disease / Premature Births / Sexually Transmitted Disease (STD) / Urinary Tract Infection1
4Not Yet RecruitingPreventionStillbirths and Infant Mortality1
4Not Yet RecruitingTreatmentAnal infection / Chlamydia Trachomatis Infection / Vaginal Infections1
4Not Yet RecruitingTreatmentAntibiotic Resistance, Bacterial / Child, Only / Death1
4Not Yet RecruitingTreatmentDepression, Anxiety / Dry Eye / Neuropathic Eye Pain / Ocular Microbiome1
4Not Yet RecruitingTreatmentDiarrhea / Dysentery, Shigella / Shigellosis1
4Not Yet RecruitingTreatmentLymphatic Filariases / Trachoma1
4Not Yet RecruitingTreatmentPost Operative Nausea and Vomiting (PONV)1
4Not Yet RecruitingTreatmentTrachoma3
4Not Yet RecruitingTreatmentUncomplicated Severe Acute Malnutrition1
4RecruitingPreventionAdherence, Treatment / Malaria in Pregnancy1
4RecruitingPreventionAntibiotic Resistance, Bacterial / Child Growth / Child Mortality / Diversity of Microbiome1
4RecruitingPreventionChildhood Mortality2
4RecruitingPreventionClinical Efficacy / Drug Kinetics / Infections, Plasmodia / Pregnancy1
4RecruitingPreventionPostpartum Endometritis / Postpartum Fever / Puerperal Sepsis1
4RecruitingPreventionProphylaxis of preeclampsia1
4RecruitingSupportive CareCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentAnal chlamydia infection1
4RecruitingTreatmentChildhood Mortality1
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentDry Eye Syndromes / Meibomian Gland Dysfunction (MGD)1
4RecruitingTreatmentPremature Births / Premature Labour / Preterm PROM (Pregnancy) / Rupture of Membranes; Delayed Delivery (Following Spontaneous Rupture) / Rupture of Membranes; Premature / Rupture of Membranes; Premature, Affecting Fetus1
4RecruitingTreatmentSalmonella Typhi Infection1
4RecruitingTreatmentScrub Typhus1
4TerminatedNot AvailableHealthy Volunteers1
4TerminatedDiagnosticMaxillary Sinusitis1
4TerminatedTreatmentChronic Bronchitis / Pneumonia / Respiratory Tract Infections (RTI)1
4Unknown StatusTreatmentBartonella Infections / Cat scratch disease1
4Unknown StatusTreatmentCervicitis / Chlamydia Trachomatis / Genital Mycoplasma Infection / Urethritis1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Unknown StatusTreatmentLiver Cirrhosis1
4Unknown StatusTreatmentM. Abscessus / Mycobacterium avium complex infection1
4Unknown StatusTreatmentMycobacterium avium complex infection1
4Unknown StatusTreatmentSalmonella Typhi Infection1
4WithdrawnNot AvailableLymphatic Filariasis / Trachoma1
4WithdrawnTreatmentChronic Bronchitis / Pneumonia, Bacterial1
Not AvailableActive Not RecruitingOtherAnti-Bacterial Agents / Microbiota1
Not AvailableActive Not RecruitingTreatmentMalnutrition in Pregnancy / Nutrition Disorders / Pregnancy / Stunting1
Not AvailableCompletedNot AvailableBacterial Infections1
Not AvailableCompletedNot AvailableBronchiectasis1
Not AvailableCompletedNot AvailableBronchitis / Sinusitis / Urinary Tract Infection1
Not AvailableCompletedNot AvailableChlamydial Infections1
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Pelvic Inflammatory Disease (PID)1
Not AvailableCompletedNot AvailableCystic Fibrosis (CF)1
Not AvailableCompletedNot AvailableDelirium / Prolonged QT Interval1
Not AvailableCompletedNot AvailableEndometritis1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableLegionella Pneumophila Infections / Legionnaires' Disease1
Not AvailableCompletedNot AvailableMaxillary Sinusitis1
Not AvailableCompletedBasic ScienceAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedBasic ScienceBronchiectasis1
Not AvailableCompletedBasic SciencePregnancy1
Not AvailableCompletedDiagnosticHealthy Volunteers1
Not AvailableCompletedDiagnosticPost-gastrointestinal bypass surgery1
Not AvailableCompletedPreventionAbscesses / Endometritis / Surgical Site Infections / Wound Infections1
Not AvailableCompletedPreventionChronic Lung Diseases1
Not AvailableCompletedPreventionChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableCompletedPreventionFirst Trimester Abortion1
Not AvailableCompletedPreventionPlasmodium Infections1
Not AvailableCompletedPreventionSinusitis1
Not AvailableCompletedTreatmentBacterial Diseases / Parasitic Diseases1
Not AvailableCompletedTreatmentBronchiectasis1
Not AvailableCompletedTreatmentBronchiolitis Obliterans (BO) / Transplantation, Bone Marrow1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableCompletedTreatmentConjunctivitis caused by chlamydia1
Not AvailableCompletedTreatmentCoughing / Idiopathic Pulmonary Fibrosis (IPF)1
Not AvailableCompletedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare7
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Tuberculosis, Mycobacterium Infection1
Not AvailableCompletedTreatmentPediculoses1
Not AvailableCompletedTreatmentPeriodontal Diseases / Periodontitis, Chronic1
Not AvailableCompletedTreatmentPeriodontitis1
Not AvailableCompletedTreatmentPneumonia, Mycoplasma1
Not AvailableCompletedTreatmentSnoring / Strep Throat1
Not AvailableNot Yet RecruitingNot AvailableCommunity Acquired Pneumonia (CAP)1
Not AvailableNot Yet RecruitingNot AvailableRespiratory Tract Infections (RTI)1
Not AvailableNot Yet RecruitingHealth Services ResearchChlamydia Trachomatis Infection1
Not AvailableNot Yet RecruitingPreventionMalaria in Pregnancy / Pregnancy1
Not AvailableNot Yet RecruitingPreventionPreterm Pre-labor Rupture of Membranes1
Not AvailableNot Yet RecruitingScreeningCervical Inflammation and Human Papilloma Virus Performance1
Not AvailableNot Yet RecruitingTreatmentPityriasis Lichenoides1
Not AvailableRecruitingNot AvailableBronchiolitis Obliterans Syndrome (BOS)1
Not AvailableRecruitingNot AvailableChildren; Infection / Newborn; Infection1
Not AvailableRecruitingDiagnosticLower Respiratory Tract Infection (LRTI)1
Not AvailableRecruitingOtherWhooping Cough1
Not AvailableRecruitingTreatmentAsthmatic Patients1
Not AvailableRecruitingTreatmentAtypical pneumonia1
Not AvailableRecruitingTreatmentHaemolytic and Uremic Syndrome1
Not AvailableRecruitingTreatmentPneumonia, Mycoplasma1
Not AvailableRecruitingTreatmentUndernutrition1
Not AvailableRecruitingTreatmentUndernutrition / Undernutrition, Lactation, Fortified Balanced Energy-protein Supplementation1
Not AvailableTerminatedNot AvailableCommunity Acquired Pneumonia (CAP)1
Not AvailableTerminatedNot AvailableBacterial blepharitis1
Not AvailableTerminatedTreatmentAcute Watery Diarrhea / Dysentery/Febrile Diarrhea1
Not AvailableTerminatedTreatmentBronchiolitis Obliterans (BO) / Graft Versus Host Disease (GVHD)1
Not AvailableTerminatedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentRefractory Mycoplasma Pneumoniae Pneumonia1
Not AvailableUnknown StatusTreatmentAsthma1
Not AvailableUnknown StatusTreatmentPeriodontitis, Chronic1
Not AvailableUnknown StatusTreatmentPneumonia1


  • Pfizer chemicals div pfizer inc
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  • Sagent strides llc
  • Teva parenteral medicines inc
  • Pfizer inc
  • Inspire pharmaceuticals inc
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  • Advanced Pharmaceutical Services Inc.
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  • Apotheca Inc.
  • APP Pharmaceuticals
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Baxter International Inc.
  • Cardinal Health
  • Catalent Pharma Solutions
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • Inspire Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
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  • Physicians Total Care Inc.
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  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Public Health Department Seattle and King County
  • Rebel Distributors Corp.
  • Redpharm Drug
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  • Sagent Pharmaceuticals
  • Sandoz
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  • Stat Rx Usa
  • Stat Scripts LLC
  • Strides Arcolab Limited
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • US Pharmaceutical Group
  • Warner Chilcott Co. Inc.
  • Wockhardt Ltd.
Dosage forms
SolutionOphthalmic1 %
SolutionOphthalmic10 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
For suspensionOral100 mg/5mL
For suspensionOral200 mg/5mL
InjectionIntravenous2.5 g/23mL
InjectionIntravenous500 mg/4.8mL
InjectionIntravenous500 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous100 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Powder, for solutionOral200 mg
Powder, for suspensionOral1 g/1
Powder, for suspensionOral100 mg
Powder, for suspensionOral100 mg/5mL
Powder, for suspensionOral1200 mg/30mL
Powder, for suspensionOral200 mg/5mL
Powder, for suspensionOral200 mg
Powder, for suspensionOral900 mg/22.5mL
Powder, for suspensionParenteral200 mg/5mL
SuspensionOral200 mg/5mL
TabletOral600 mg
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral600 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
TabletOral250 mg/1
TabletOral500 mg/1
TabletOral600 mg/1
TabletOral250 mg
TabletOral500 mg
Powder, for suspensionOral
Powder, for solutionIntravenous
Powder, for suspensionOral2 g/60mL
Granule, for suspension, extended releaseOral
Unit descriptionCostUnit
Zithromax 3 1 gm Packets Box118.26USD box
Azithromycin 2.5 gm bulk vial75.6USD each
Zmax adult-ped 2 g/60 ml susp70.39USD each
Zithromax Tri-Pak 3 500 mg tablet Disp Pack69.67USD disp
Zithromax Z-Pak 6 250 mg tablet Disp Pack68.62USD disp
Zmax 2 g/60 ml susp sr67.04USD each
Zmax pediatric 2 g/60 ml susp67.04USD each
Zithromax 200 mg/5ml Suspension 30ml Bottle52.0USD bottle
Zithromax 100 mg/5ml Suspension 15ml Bottle51.6USD bottle
Zithromax 200 mg/5ml Suspension 15ml Bottle50.46USD bottle
Zithromax 200 mg/5ml Suspension 22.5ml Bottle50.46USD bottle
Azithromycin 3 500 mg tablet Disp Pack48.52USD disp
Azithromycin 6 250 mg tablet Disp Pack48.52USD disp
Azasite 1% eye drops42.85USD ml
Zithromax i.v. 500 mg vial34.39USD vial
Azithromycin 200 mg/5ml Suspension 15ml Bottle34.25USD bottle
Zithromax 600 mg tablet27.22USD tablet
Zithromax 500 mg tablet22.68USD tablet
Zithromax tri-pak 500 mg tablet22.24USD tablet
Azithromycin 600 mg tablet19.04USD tablet
Azithromycin 500 mg tablet15.87USD tablet
Trimox 125 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 150ml Bottle11.99USD bottle
Trimox 250 mg/5ml Suspension 80ml Bottle11.99USD bottle
Zithromax 250 mg z-pak tablet11.12USD tablet
Azithromycin i.v. 500 mg vial11.09USD each
Azithromycin powder10.89USD g
Zithromax 250 mg tablet9.41USD tablet
Azithromycin 250 mg tablet6.33USD tablet
Apo-Azithromycin 250 mg Tablet3.11USD tablet
Co Azithromycin 250 mg Tablet3.11USD tablet
Mylan-Azithromycin 250 mg Tablet3.11USD tablet
Novo-Azithromycin 250 mg Tablet3.11USD tablet
Phl-Azithromycin 250 mg Tablet3.11USD tablet
Pms-Azithromycin 250 mg Tablet3.11USD tablet
Ratio-Azithromycin 250 mg Tablet3.11USD tablet
Sandoz Azithromycin 250 mg Tablet3.11USD tablet
Zithromax 40 mg/ml Suspension1.7USD ml
Zithromax 20 mg/ml Suspension1.2USD ml
Novo-Azithromycin 40 mg/ml Suspension0.95USD ml
Pms-Azithromycin 40 mg/ml Suspension0.95USD ml
Sandoz Azithromycin 40 mg/ml Suspension0.95USD ml
Novo-Azithromycin 20 mg/ml Suspension0.67USD ml
Pms-Azithromycin 20 mg/ml Suspension0.67USD ml
Sandoz Azithromycin 20 mg/ml Suspension0.67USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent NumberPediatric ExtensionApprovedExpires (estimated)
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more


Experimental Properties
melting point (°C)126
water solubilitysoluble in ethanol and DSMO, minimally soluble in water
Predicted Properties
Water Solubility0.514 mg/mLALOGPS
pKa (Strongest Acidic)12.43ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area180.08 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity194.11 m3·mol-1ChemAxon
Polarizability83.11 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Human Intestinal Absorption-0.5518
Blood Brain Barrier-0.9739
Caco-2 permeable-0.7578
P-glycoprotein substrateSubstrate0.8765
P-glycoprotein inhibitor IInhibitor0.8513
P-glycoprotein inhibitor IINon-inhibitor0.8893
Renal organic cation transporterNon-inhibitor0.8753
CYP450 2C9 substrateNon-substrate0.8373
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6403
CYP450 1A2 substrateNon-inhibitor0.9295
CYP450 2C9 inhibitorNon-inhibitor0.9021
CYP450 2D6 inhibitorNon-inhibitor0.8904
CYP450 2C19 inhibitorNon-inhibitor0.9023
CYP450 3A4 inhibitorNon-inhibitor0.9533
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9751
Ames testNon AMES toxic0.9133
BiodegradationNot ready biodegradable0.9673
Rat acute toxicity2.5423 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9929
hERG inhibition (predictor II)Non-inhibitor0.8555
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004l-0309050000-5e1be028a242f0d384eb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f6t-0300030900-1a7ea512a0aa566e59ed
MS/MS Spectrum - , positiveLC-MS/MSsplash10-066r-4911100000-f759f24274aebce8e08c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-052f-3912280200-df9a72a4769570064ef9


This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Organic compounds
Super Class
Organic oxygen compounds
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Alternative Parents
Macrolides and analogues / O-glycosyl compounds / Oxanes / Monosaccharides / Tertiary alcohols / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters
show 11 more
Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Monosaccharide / Oxane / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic (CHEBI:2955)


Enteric bacteria and other eubacteria
Pharmacological action
In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.
  1. Ng LK, Martin I, Liu G, Bryden L: Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae. Antimicrob Agents Chemother. 2002 Sep;46(9):3020-5. [PubMed:12183262]
  2. Jalava J, Vaara M, Huovinen P: Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes. Ann Clin Microbiol Antimicrob. 2004 May 6;3:5. [PubMed:15128458]
  3. Pereyre S, Renaudin H, Charron A, Bebear C, Bebear CM: Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to erythromycin and azithromycin. J Antimicrob Chemother. 2006 Apr;57(4):753-6. Epub 2006 Feb 7. [PubMed:16464889]
  4. Marvig RL, Sondergaard MS, Damkiaer S, Hoiby N, Johansen HK, Molin S, Jelsbak L: Mutations in 23S rRNA confer resistance against azithromycin in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2012 Aug;56(8):4519-21. doi: 10.1128/AAC.00630-12. Epub 2012 May 29. [PubMed:22644032]
Pharmacological action
Curator comments
Data for this target action are limited at this time.
General Function
Protein-arginine deiminase activity
Specific Function
Catalyzes the citrullination/deimination of arginine residues of proteins such as histones, thereby playing a key role in histone code and regulation of stem cell maintenance. Citrullinates histone...
Gene Name
Uniprot ID
Uniprot Name
Protein-arginine deiminase type-4
Molecular Weight
74078.65 Da
  1. Knuckley B, Luo Y, Thompson PR: Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. [PubMed:17964793]


1. Cytochrome P450 3A4
Pharmacological action
Curator comments
Data regarding this enzyme action are limited and this enzyme action is unlikely to result in clinically significant effects.
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
Uniprot ID
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
  1. Fohner AE, Sparreboom A, Altman RB, Klein TE: PharmGKB summary: Macrolide antibiotic pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2017 Apr;27(4):164-167. doi: 10.1097/FPC.0000000000000270. [PubMed:28146011]
  2. Zhou SF, Xue CC, Yu XQ, Li C, Wang G: Clinically important drug interactions potentially involving mechanism-based inhibition of cytochrome P450 3A4 and the role of therapeutic drug monitoring. Ther Drug Monit. 2007 Dec;29(6):687-710. doi: 10.1097/FTD.0b013e31815c16f5. [PubMed:18043468]


Pharmacological action
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
Uniprot ID
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
  1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742]
  2. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. [PubMed:14744620]
  3. Sugie M, Asakura E, Zhao YL, Torita S, Nadai M, Baba K, Kitaichi K, Takagi K, Takagi K, Hasegawa T: Possible involvement of the drug transporters P glycoprotein and multidrug resistance-associated protein Mrp2 in disposition of azithromycin. Antimicrob Agents Chemother. 2004 Mar;48(3):809-14. [PubMed:14982769]
  4. McMullan BJ, Mostaghim M: Prescribing azithromycin. Aust Prescr. 2015 Jun;38(3):87-9. Epub 2015 Jun 1. [PubMed:26648627]
Pharmacological action
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
Uniprot ID
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
  1. Sugie M, Asakura E, Zhao YL, Torita S, Nadai M, Baba K, Kitaichi K, Takagi K, Takagi K, Hasegawa T: Possible involvement of the drug transporters P glycoprotein and multidrug resistance-associated protein Mrp2 in disposition of azithromycin. Antimicrob Agents Chemother. 2004 Mar;48(3):809-14. [PubMed:14982769]
  2. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. [PubMed:14744620]
  3. Yamaguchi S, Zhao YL, Nadai M, Yoshizumi H, Cen X, Torita S, Takagi K, Takagi K, Hasegawa T: Involvement of the drug transporters p glycoprotein and multidrug resistance-associated protein Mrp2 in telithromycin transport. Antimicrob Agents Chemother. 2006 Jan;50(1):80-7. doi: 10.1128/AAC.50.1.80-87.2006. [PubMed:16377671]
  4. Fohner AE, Sparreboom A, Altman RB, Klein TE: PharmGKB summary: Macrolide antibiotic pathway, pharmacokinetics/pharmacodynamics. Pharmacogenet Genomics. 2017 Apr;27(4):164-167. doi: 10.1097/FPC.0000000000000270. [PubMed:28146011]

Drug created on June 13, 2005 07:24 / Updated on February 25, 2020 00:01