Identification

Name
Azithromycin
Accession Number
DB00207
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.

In March 2020, a small study was funded by the French government to investigate the treatment of COVID-19 with a combination of azithromycin and the anti-malaria drug hydroxychloroquine. The results were positive, all patients taking the combination were virologically cured within 6 days of treatment, however, larger studies are required.9

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 748.9845
Monoisotopic: 748.508525778
Chemical Formula
C38H72N2O12
Synonyms
  • Azithromycin
  • Azithromycine
  • Azithromycinum
  • Azitromicina
External IDs
  • CP 62993
  • CP-62,993
  • CP-62993
  • DRG-0104
  • XZ 405
  • XZ 450
  • XZ-450

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
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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 ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
UProtein-arginine deiminase type-4
inhibitor
Humans
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

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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 observed 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
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.
DrugInteraction
AbametapirThe serum concentration of Azithromycin can be increased when it is combined with Abametapir.
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.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Azithromycin.
AcalabrutinibThe metabolism of Azithromycin can be decreased when combined with Acalabrutinib.
AcebutololThe risk or severity of QTc prolongation can be increased when Azithromycin is combined with Acebutolol.
AcenocoumarolThe risk or severity of adverse effects can be increased when Azithromycin is combined with Acenocoumarol.
AcetaminophenThe metabolism of Azithromycin can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Azithromycin can be decreased when combined with Acetazolamide.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Azithromycin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.

Products

Product Ingredients
IngredientUNIICASInChI Key
Azithromycin dihydrate5FD1131I7S117772-70-0SRMPHJKQVUDLQE-KUJJYQHYSA-N
Azithromycin monohydrateJTE4MNN1MD121470-24-4HQUPLSLYZHKKQT-WVVFQGGUSA-N
Product Images
International/Other Brands
Azenil / Azibiot / Azifast / Azigram / Azimakrol / Azin / Azithrocin / Azitromax / Azitromin / Aztrin / Hemomycin / Misultina / Penalox / Sumamed / Vinzam / Zifin / Zitrocin / Zitrotek
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act AzithromycinTabletOralActavis Pharma Company2005-11-022019-06-24Canada
Act AzithromycinTabletOralActavis Pharma Company2005-11-022018-06-12Canada
AzaSITESolution / drops10 mg/1mLOphthalmicAkorn2014-05-14Not applicableUs
AzaSITESolution1 %OphthalmicInsite Vision IncorporatedNot applicableNot applicableCanada
AzaSiteSolution10 mg/1mLOphthalmicInspire Pharmaceuticals, Inc.2007-07-162015-08-31Us
AzaSITESolution1 %OphthalmicInspire Pharmaceuticals, Inc.Not applicableNot applicableCanada
AzithromycinTablet250 mgOralAltamed Pharma2019-05-07Not applicableCanada
AzithromycinTablet250 mgOral4513347 Canada Inc.Not applicableNot applicableCanada
AzithromycinPowder, for suspension1 g/1OralRpk Pharmaceuticals, Inc.1999-02-12Not applicableUs
AzithromycinPowder, for suspension100 mgOralDominion PharmacalNot applicableNot applicableCanada
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 EndRegionImage
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
AzithromycinTablet, film coated250 mg/1OralSandoz Inc2005-11-14Not 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.

    Learn more
  • Product Code
    Product Code

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

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Azithromycin DihydrateAzithromycin dihydrate (500 mg/1)Tablet, coatedOralLannett Company, Inc.2020-04-18Not applicableUs
ZithromaxAzithromycin dihydrate (250 mg/1)Tablet, film coatedOralPfizer Laboratories Div Pfizer Inc2020-04-30Not applicableUs

Categories

ATC Codes
J01RA07 — Azithromycin, fluconazole and secnidazoleS01AA26 — AzithromycinJ01FA10 — Azithromycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino acid or derivatives / Aminoglycoside core / Azacycle / Carbonyl group / Carboxylic acid derivative
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic (CHEBI:2955)

Chemical Identifiers

UNII
J2KLZ20U1M
CAS number
83905-01-5
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

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. Gautret P, Lagier JC, Parola P, Hoang VT, Meddeb L, Mailhe M, Doudier B, Courjon J, Giordanengo V, Vieira VE, Dupont HT, Honore S, Colson P, Chabriere E, La Scola B, Rolain JM, Brouqui P, Raoult D: Hydroxychloroquine and azithromycin as a treatment of COVID-19: results of an open-label non-randomized clinical trial. Int J Antimicrob Agents. 2020 Mar 20:105949. doi: 10.1016/j.ijantimicag.2020.105949. [PubMed:32205204]
  10. Zithromax FDA label [File]
  11. Azithromycin, Ophthalmic FDA label [File]
  12. Sandoz Azithromycin Canadian Monograph [File]
Human Metabolome Database
HMDB0014352
KEGG Compound
C06838
PubChem Compound
447043
PubChem Substance
46507743
ChemSpider
10482163
BindingDB
50373918
RxNav
1299904
ChEBI
2955
ChEMBL
CHEMBL529
ZINC
ZINC000085537026
Therapeutic Targets Database
DNC001539
PharmGKB
PA448519
PDBe Ligand
ZIT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
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
4Active Not RecruitingPreventionAntibiotic Resistance, Bacterial / Child Growth / Child Mortality / Diversity of Microbiome1
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
4CompletedPreventionPremature Births1
4CompletedPreventionTrichiasis1

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
TabletOral
SolutionOphthalmic1 %
SolutionOphthalmic10 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
PowderParenteral200 MG/5ML
Tablet, film coatedOral250 MG
Tablet, film coatedOral500 MG
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 suspensionOral100 mg
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
Tablet, coatedOral500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
TabletOral250 mg/1
TabletOral500 mg/1
TabletOral600 mg/1
PowderParenteral5 ML
TabletOral250 mg
TabletOral500 mg
Powder, for suspensionOral
CapsuleOral
Powder, for solutionIntravenous
Powder, for suspensionOral2 g/60mL
Granule, for suspension, extended releaseOral
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)Region
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
Additional Data Available
  • Filed On
    Filed On

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

    Learn more

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

Targets

Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
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.
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]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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]
  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]

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 August 04, 2020 17:12

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