Identification

Name
Azithromycin
Accession Number
DB00207  (APRD00397)
Type
Small Molecule
Groups
Approved
Description

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].

Structure
Thumb
Synonyms
  • 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 AzithromycinTablet600 mgOralActavis Pharma Company2005-11-02Not applicableCanada
Act AzithromycinTablet250 mgOralActavis Pharma Company2005-11-02Not applicableCanada
AzaSiteSolution10 mg/1mLOphthalmicInspire Pharmaceuticals, Inc.2007-07-162015-08-31Us
AzaSITESolution / drops10 mg/1mLOphthalmicAkorn2014-05-14Not applicableUs
AzaSITESolution1 %OphthalmicInsite Vision IncorporatedNot applicableNot applicableCanada
AzaSITESolution1 %OphthalmicInspire Pharmaceuticals, Inc.Not applicableNot applicableCanada
AzithromycinTablet, film coated600 mg/1OralRemedy Repack2012-07-212013-07-22Us
AzithromycinPowder, for suspension1 g/1OralRpk Pharmaceuticals, Inc.1999-02-12Not applicableUs
AzithromycinTablet250 mgOralSanis Health Inc2010-02-01Not applicableCanada
AzithromycinTablet600 mgOralSanis Health Inc2010-02-012014-08-01Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-azithromycinTablet250 mgOralApotex Corporation2005-11-02Not applicableCanada
Apo-azithromycin ZTablet250 mgOralApotex Corporation2014-03-06Not applicableCanada
Ava-azithromycinPowder, for suspension200 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinPowder, for suspension100 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinTablet250 mgOralAvanstra Inc2011-09-192014-08-21Canada
AzithromycinTablet, film coated250 mg/1OralRpk Pharmaceuticals, Inc.2006-01-06Not applicableUs
AzithromycinTablet, film coated250 mg/1OralCardinal Health2008-04-022015-06-30Us
AzithromycinTablet, film coated250 mg/1OralTEVA Pharmaceutical Industries Ltd.2010-03-242010-04-22Us
AzithromycinPowder, for suspension200 mg/5mLOralCadila Pharnmaceuticals2018-08-06Not applicableUs
AzithromycinTablet, film coated250 mg/1OralNucare Pharmaceuticals,inc.2006-01-06Not applicableUs
International/Other Brands
Azenil / Azibiot / Azifast / Azigram / Azimakrol / Azin / Azithrocin / Azitromax / Azitromin / Aztrin / Hemomycin / Misultina / Penalox / Sumamed / Vinzam / Zifin / Zitrocin / Zitrotek
Categories
UNII
J2KLZ20U1M
CAS number
83905-01-5
Weight
Average: 748.9845
Monoisotopic: 748.508525778
Chemical Formula
C38H72N2O12
InChI Key
MQTOSJVFKKJCRP-BICOPXKESA-N
InChI
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
IUPAC Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O

Pharmacology

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 [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].

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.

Associated Conditions
Pharmacodynamics

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].

TargetActionsOrganism
A23S rRNA
inhibitor
Enteric bacteria and other eubacteria
UProtein-arginine deiminase type-4
inhibitor
Humans
ABacterial 50S Ribosomal Subunit
inhibitor
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 [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].

Metabolism

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]

Clearance

Mean apparent plasma cl=630 mL/min (following single 500 mg oral and i.v. dose) [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 [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
Pathways
PathwayCategory
Azithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(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.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Azithromycin.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Azithromycin is combined with 4-hydroxycoumarin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Azithromycin.
6-Deoxyerythronolide BThe metabolism of Azithromycin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Azithromycin.
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.
Food Interactions
  • Do not take Aluminum or magnesium antacids or supplements while on this medication.
  • Take on empty stomach: 1 hour before or 2 hours after meals.

References

Synthesis Reference

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

US6013778
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
HMDB0014352
KEGG Compound
C06838
PubChem Compound
447043
PubChem Substance
46507743
ChemSpider
10482163
BindingDB
50373918
ChEBI
2955
ChEMBL
CHEMBL529
Therapeutic Targets Database
DNC001539
PharmGKB
PA448519
HET
ZIT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Azithromycin
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
MSDS
Download (34.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
0Not Yet RecruitingTreatmentAcne Vulgaris1
0Not Yet RecruitingTreatmentBMI >30 kg/m2 / Induction of Labor Affected Fetus / Newborn1
0RecruitingTreatmentOsteomyelitis1
0RecruitingTreatmentRespiratory Syncytial Virus (RSV)1
1CompletedNot AvailableFasting1
1CompletedNot AvailableHealthy Volunteers7
1CompletedNot AvailableProphylaxis of Malaria1
1CompletedBasic ScienceInflammatory Reaction1
1CompletedBasic SciencePharmacokinetics1
1CompletedBasic SciencePrebiotics / Probiotics / Quorum Sensing / Sepsis1
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
1CompletedTreatmentEye Infections, Bacterial5
1CompletedTreatmentGonorrhoea1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Toxoplasmosis, Cerebral1
1CompletedTreatmentInfection NOS1
1RecruitingOtherPhysiological Response to Antibiotics1
1RecruitingTreatmentConjunctivitis, Bacterial1
1WithdrawnPreventionAcute Chest Syndrome / Sickle Cell Disorders1
1, 2Not Yet RecruitingTreatmentEbola Virus Disease1
1, 2RecruitingPreventionRandomized Controll Trial1
1, 2TerminatedPreventionBacteria Infection / Respiratory Tract Infections (RTI)1
1, 2WithdrawnOtherSickle Cell Disorders1
1, 2WithdrawnPreventionMalaria caused by Plasmodium falciparum1
1, 2WithdrawnTreatmentGraves Ophthalmopathy1
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
2CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii1
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
2CompletedTreatmentMalaria caused by Plasmodium falciparum1
2CompletedTreatmentObliterative Bronchiolitis1
2CompletedTreatmentObsessive Compulsive Disorder (OCD) / PANS / Pediatric Autoimmune Neuropsychiatric Disorders Associated With Streptococcal Infections1
2CompletedTreatmentOnchocerciasis1
2CompletedTreatmentPeriodontitis, Chronic1
2CompletedTreatmentPlasmodium Falciparum Malaria1
2CompletedTreatmentPosterior Blepharitis1
2CompletedTreatmentRsv Bronchiolitis1
2CompletedTreatmentUncomplicated Falciparum Malaria1
2CompletedTreatmentUrethritis1
2CompletedTreatmentBacterial blepharitis3
2Not Yet RecruitingTreatmentLymphatic Filariasis / Traumas / Yaws1
2RecruitingPreventionHuman Immunodeficiency Virus (HIV) / Pregnancy Malaria / Sexually Transmitted Infections (STIs)1
2RecruitingTreatmentAsthma Bronchial1
2RecruitingTreatmentChlamydophila Pneumoniae Infections / Coronary Heart Disease (CHD)1
2RecruitingTreatmentChronic Asthma1
2RecruitingTreatmentDiabetes Mellitus (DM) / Diabetes, Diabetes Mellitus Type 1 / Diet Modification / Endocrine System Diseases / Glucose Metabolism Disorders / Inflammatory Reaction / Insulin Dependent Diabetes / Metabolic Diseases / Type 1 Insulin-Dependent Diabetes Mellitus1
2RecruitingTreatmentPulmonary Tuberculosis (TB)1
2RecruitingTreatmentSarcoidosis; Antimycobacterial Therapy1
2TerminatedPreventionBronchiectasis / Chronic Bronchitis / Pulmonary Diseases1
2TerminatedPreventionChronic Obstructive Pulmonary Disease (COPD) / Tracheostomy care1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2TerminatedPreventionPseudomonas Infections / Ventilator-Associated Pneumonia (VAP)1
2TerminatedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
2TerminatedTreatmentGastroparesis1
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, 3CompletedScreeningLow Risk of Preterm Delivery1
2, 3CompletedTreatmentMalaria caused by Plasmodium falciparum2
2, 3CompletedTreatmentPlasmodium Falciparum Malaria1
2, 3Not Yet RecruitingTreatmentMycobacterium avium complex infection / Nontuberculous Mycobacterium Infection1
2, 3RecruitingPreventionCampylobacter Infections / Enteric Pathogens / Malnutrition; Protein / Stunting1
2, 3RecruitingTreatmentRespiratory Syncytial Virus, Bronchiolitis1
2, 3TerminatedTreatmentCommunity-Acquired Bacterial Pneumonia (CABP)1
2, 3TerminatedTreatmentLeishmaniasis, Cutaneous1
2, 3TerminatedTreatmentMalaria caused by Plasmodium falciparum1
2, 3WithdrawnTreatmentTrachoma1
3Active Not RecruitingPreventionMalignant Hematological Diseases1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)2
3Active Not RecruitingTreatmentNon Cystic Fibrosis Bronchiectasis in Children1
3Active Not RecruitingTreatmentYaws1
3CompletedPreventionAnemias / Malaria in Pregnancy / Sexually Transmitted Infections (STIs)1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction1
3CompletedPreventionNeonatal Infections1
3CompletedPreventionPlasmodium Infections / Respiratory Tract Infections (RTI)1
3CompletedTreatmentAbdominal Pain (AP) / Fevers / Severe or persistent diarrhea / Vomiting1
3CompletedTreatmentAsthma Bronchial3
3CompletedTreatmentAsthma Bronchial / Wheezing1
3CompletedTreatmentBlepharoconjunctivitis1
3CompletedTreatmentChlamydial Infections1
3CompletedTreatmentCholera2
3CompletedTreatmentChronic Bronchitis1
3CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Coughing1
3CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
3CompletedTreatmentConjunctivitis, Bacterial3
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
3CompletedTreatmentNeglected Tropical Disease / Treponema Infection / Yaws1
3CompletedTreatmentOtitis Media (OM)1
3CompletedTreatmentPelvic Inflammatory Disease (PID)1
3CompletedTreatmentPharyngitis / Tonsillitis1
3CompletedTreatmentPlasmodium Falciparum Infection1
3CompletedTreatmentPlasmodium Infections2
3CompletedTreatmentPneumonia2
3CompletedTreatmentReactive Arthritis / Reiter's Disease1
3CompletedTreatmentSyphilis1
3CompletedTreatmentTrachoma1
3CompletedTreatmentUncomplicated Urogenital Gonorrhea1
3CompletedTreatmentUrethritis1
3CompletedTreatmentYaws1
3CompletedTreatmentBacterial blepharitis2
3Not Yet RecruitingDiagnosticPneumonia / Respiratory Tract Infections (RTI) / Tuberculosis Infection1
3Not Yet RecruitingTreatmentLymphatic Filariases / Oesophagostomiasis / Scabies / Trachoma / Yaws1
3RecruitingPreventionBronchiectasis / Cystic Fibrosis (CF)1
3RecruitingPreventionNeonatal Sepsis1
3RecruitingTreatmentChronic Cough (CC)1
3RecruitingTreatmentChronic Lung Diseases / Human Immunodeficiency Virus (HIV) Infections1
3RecruitingTreatmentLung Infection / Mycobacterium avium complex infection1
3RecruitingTreatmentPreterm Premature Rupture of Membranes (PPROM)1
3RecruitingTreatmentUndifferentiated Febrile Illness1
3RecruitingTreatmentSevere or persistent diarrhea1
3TerminatedTreatmentAsymptomatic Parasitemia In Pregnancy1
3TerminatedTreatmentCervicitis / Vaginitis Bacterial1
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
3WithdrawnTreatmentBlepharoconjunctivitis1
3WithdrawnTreatmentCommunity Acquired Pneumonia (CAP)1
4Active Not RecruitingTreatmentChild's Development1
4CompletedNot AvailableHealthy Volunteers1
4CompletedNot AvailablePregnancy1
4CompletedNot AvailableRespiratory Tract Infections (RTI)1
4CompletedPreventionBronchiolitis Obliterans Syndrome (BOS) / Lymphocytic Bronchiolitis / Rejection, Transplant / Respiratory Tract Infections (RTI)1
4CompletedPreventionTrichiasis1
4CompletedSupportive CareBacterial Infections / Cataract Extraction / Eye Infections1
4CompletedSupportive CareBacterial Infections / Eye Infections2
4CompletedTreatmentAcute Otitis Media1
4CompletedTreatmentAsthma Bronchial4
4CompletedTreatmentBacterial Vaginosis (BV)1
4CompletedTreatmentBronchiectasis1
4CompletedTreatmentChildhood Mortality1
4CompletedTreatmentChlamydia Trachomatis / Human Immunodeficiency Virus (HIV) / Neisseria Gonorrhoeae Infection1
4CompletedTreatmentChlamydia Trachomatis / Trachoma1
4CompletedTreatmentChlamydial Infections / Trachoma1
4CompletedTreatmentChronic Rhinosinusitis / High-risk Patients1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentContact Lens Dry Eye1
4CompletedTreatmentCrohn's Disease (CD)1
4CompletedTreatmentCystic Fibrosis (CF)2
4CompletedTreatmentDisorders Related to Lung Transplantation1
4CompletedTreatmentDry Eye Syndrome (DES)1
4CompletedTreatmentGonorrhoea1
4CompletedTreatmentHelicobacter Pylori / Indigestion / Peptic Ulcers1
4CompletedTreatmentImpetigo / Scabies / Yaws1
4CompletedTreatmentLymphocytic Bronchi(Oli)Tis Post-lung Transplantation1
4CompletedTreatmentPneumonia1
4CompletedTreatmentSinusitis2
4CompletedTreatmentTonsillitis1
4CompletedTreatmentTrachoma1
4CompletedTreatmentUrinary Bladder, Overactive1
4CompletedTreatmentBacterial blepharitis5
4CompletedTreatmentSevere or persistent diarrhea1
4Enrolling by InvitationTreatmentChildhood Mortality1
4Enrolling by InvitationTreatmentCystic Fibrosis (CF)1
4Not Yet RecruitingBasic ScienceMicrobial Colonization1
4Not Yet RecruitingDiagnosticHelminth Infection1
4Not Yet RecruitingPreventionAntibiotic Resistance, Bacterial / Child Growth / Child Mortality / Diversity of Microbiome1
4Not Yet RecruitingPreventionChildhood Mortality2
4Not Yet RecruitingTreatmentAnal infection / Chlamydia Trachomatis Infection / Vaginal Infections1
4Not Yet RecruitingTreatmentPost-Operative Nausea and Vomiting (PONV)1
4Not Yet RecruitingTreatmentTrachoma2
4Not Yet RecruitingTreatmentUncomplicated Severe Acute Malnutrition1
4RecruitingPreventionClinical Efficacy / Drug Kinetics / Infections, Plasmodia / Pregnancy1
4RecruitingPreventionFlu caused by Influenza1
4RecruitingPreventionPostpartum Endometritis / Postpartum Fever / Puerperal Sepsis1
4RecruitingPreventionTrachoma1
4RecruitingTreatmentAnal chlamydia infection1
4RecruitingTreatmentChildhood Mortality1
4RecruitingTreatmentCo-Infection / Malnutrition / Plasmodium Infections / Pneumonia / Severe or persistent diarrhea / The Mortality Rate1
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentCystic Fibrosis (CF)1
4RecruitingTreatmentDry Eye Syndromes / Meibomian Gland Dysfunction (MGD)1
4TerminatedNot AvailableHealthy Volunteers1
4TerminatedDiagnosticMaxillary Sinusitis1
4TerminatedTreatmentAsthma Bronchial1
4TerminatedTreatmentChronic Bronchitis / Pneumonia / Respiratory Tract Infections (RTI)1
4TerminatedTreatmentPneumonia1
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
4WithdrawnPreventionEndometritis1
4WithdrawnTreatmentChronic Bronchitis / Pneumonia, Bacterial1
4WithdrawnTreatmentTrachoma1
Not AvailableActive Not RecruitingOtherAnti-Bacterial Agents / Microbiota1
Not AvailableCompletedNot AvailableBronchiectasis1
Not AvailableCompletedNot AvailableBronchitis / Sinusitis / Urinary Tract Infections (UTIs)1
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 AvailableEndometritis1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableLegionella Pneumophila Infections / Legionnaires' Disease1
Not AvailableCompletedBasic ScienceBronchiectasis1
Not AvailableCompletedBasic SciencePregnancy1
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 AvailableCompletedTreatmentConjunctivitis caused by chlamydia1
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 AvailableCompletedTreatmentObliterative Bronchiolitis / Transplantation, Bone Marrow1
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 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 AvailableRecruitingTreatmentCoughing / Idiopathic Pulmonary Fibrosis (IPF)1
Not AvailableRecruitingTreatmentHaemolytic and Uremic Syndrome1
Not AvailableRecruitingTreatmentMalnutrition in Pregnancy / Nutrition Disorders / Pregnancy / Stunting1
Not AvailableRecruitingTreatmentPneumonia, Mycoplasma1
Not AvailableRecruitingTreatmentUndernutrition / Undernutrition, Lactation, Fortified Balanced Energy-protein Supplementation1
Not AvailableTerminatedNot AvailableBacterial blepharitis1
Not AvailableTerminatedTreatmentAcute Watery Diarrhea / Dysentery/Febrile Diarrhea1
Not AvailableTerminatedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentGraft Versus Host Disease (GVHD) / Obliterative Bronchiolitis1
Not AvailableTerminatedTreatmentRefractory Mycoplasma Pneumoniae Pneumonia1
Not AvailableUnknown StatusTreatmentAsthma Bronchial1
Not AvailableUnknown StatusTreatmentPneumonia1

Pharmacoeconomics

Manufacturers
  • Pfizer chemicals div pfizer inc
  • Pfizer global research development
  • Pliva inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Pfizer central research
  • App pharmaceuticals llc
  • Gland pharma ltd
  • Hospira inc
  • Pliva hrvatska doo
  • Sagent strides llc
  • Teva parenteral medicines inc
  • Pfizer inc
  • Inspire pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • 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
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patheon Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Public Health Department Seattle and King County
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sagent Pharmaceuticals
  • Sandoz
  • Sicor Pharmaceuticals
  • Southwood Pharmaceuticals
  • 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
FormRouteStrength
TabletOral250 mg
TabletOral600 mg
SolutionOphthalmic1 %
SolutionOphthalmic10 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
For suspensionOral100 mg/5mL
For suspensionOral200 mg/5mL
InjectionIntravenous2.5 g/23mL
InjectionIntravenous500 mg/10mL
InjectionIntravenous500 mg/4.8mL
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/5mL
Powder, for suspensionOral1200 mg/30mL
Powder, for suspensionOral200 mg
Powder, for suspensionOral200 mg/5mL
Powder, for suspensionOral900 mg/22.5mL
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
TabletOral500 mg
Powder, for suspensionOral100 mg
CapsuleOral250 mg
Powder, for solutionIntravenous500 mg
Powder, for suspensionOral2 g/60mL
Granule, for suspension, extended releaseOral2 g
Prices
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5192535No1993-03-092010-03-09Us
CA2467611No2010-03-302024-05-18Canada
CA2148071No2000-10-172015-04-27Canada
US6984403No2006-01-102024-02-14Us
US7887844No2011-02-152024-02-14Us
US6268489No2001-07-312018-07-31Us
US6068859No2000-05-302017-05-30Us
US6159458No2000-12-122017-11-04Us
US6239113No2001-05-292019-03-31Us
US6569443No2003-05-272019-03-31Us
US6861411No2005-03-012018-11-25Us
US7056893No2006-06-062019-03-31Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)126http://www.chemspider.com/Chemical-Structure.2298410.html
water solubilitysoluble in ethanol and DSMO, minimally soluble in waterhttps://www.caymanchem.com/pdfs/15004.pdf
logP3.03http://www.medicines.org.au/files/afpazith.pdf
pKa8.5https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0174372
Predicted Properties
PropertyValueSource
Water Solubility0.514 mg/mLALOGPS
logP3.03ALOGPS
logP2.44ChemAxon
logS-3.2ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
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
CarcinogenicityNon-carcinogens0.9397
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
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

Taxonomy

Description
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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
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
Substituents
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)

Targets

1. 23S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
References
  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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
PADI4
Uniprot ID
Q9UM07
Uniprot Name
Protein-arginine deiminase type-4
Molecular Weight
74078.65 Da
References
  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]
3. Bacterial 50S Ribosomal Subunit
Kind
Protein group
Organism
Not Available
Pharmacological action
Yes
Actions
Inhibitor
This is a broad protein group that is comprised of the 50S subunit of many bacterial organisms.
References
  1. 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]
  2. Champney WS, Burdine R: Macrolide antibiotic inhibition of translation and 50S ribosomal subunit assembly in methicillin-resistant Staphylococcus aureus cells. Microb Drug Resist. 1998 Fall;4(3):169-74. [PubMed:9818968]
  3. Champney WS, Burdine R: Azithromycin and clarithromycin inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells. Curr Microbiol. 1998 Feb;36(2):119-23. [PubMed:9425251]
  4. Petropoulos AD, Kouvela EC, Starosta AL, Wilson DN, Dinos GP, Kalpaxis DL: Time-resolved binding of azithromycin to Escherichia coli ribosomes. J Mol Biol. 2009 Jan 30;385(4):1179-92. doi: 10.1016/j.jmb.2008.11.042. Epub 2008 Nov 27. [PubMed:19071138]
  5. Zithromax FDA label [File]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  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]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  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 18, 2019 20:23