Azithromycin

Identification

Summary

Azithromycin is a macrolide antibiotic used to treat a variety of bacterial infections.

Brand Names

Azasite, Zithromax, Zmax

Generic Name

Azithromycin

DrugBank Accession Number

DB00207

Background

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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Azithromycin (DB00207)

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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

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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.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Acute bacterial sinusitis		••••••••••••		••••••
Treatment of	Acute otitis media		••••••••••••		••••••••• ••••••••
Treatment of	Acute bacterial exacerbation of copd caused by haemophilus influenza infections, moraxella catarrhalis infection, streptococcus pneumoniae infections		••••••••••••		••••••
Treatment of	Bacterial conjunctivitis		••••••••••••			••••••••
Treatment of	Bacterial sinusitis		••••••••••••		••••••••• ••••••••

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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.

Target	Actions	Organism
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

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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.

Pathways

Pathway	Category
Azithromycin Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Azithromycin can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Azithromycin can be increased when combined with Abatacept.
Abciximab	The risk or severity of adverse effects can be increased when Azithromycin is combined with Abciximab.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Azithromycin.
Acalabrutinib	The metabolism of Acalabrutinib can be decreased when combined with Azithromycin.

Food Interactions

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

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Azithromycin dihydrate	5FD1131I7S	117772-70-0	SRMPHJKQVUDLQE-KUJJYQHYSA-N
Azithromycin hemiethanolate monohydrate	S548K9P0TK	554432-19-8	FEWUYCASOAUDHD-LCPFZDPDSA-N
Azithromycin monohydrate	JTE4MNN1MD	121470-24-4	HQUPLSLYZHKKQT-WVVFQGGUSA-N

Product Images

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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

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Act Azithromycin	Tablet	250 mg	Oral	Actavis Pharma Company	2005-11-02	2018-06-12
Act Azithromycin	Tablet	600 mg	Oral	Actavis Pharma Company	2005-11-02	2019-06-24
AzaSite	Solution	10 mg/1mL	Ophthalmic	Inspire Pharmaceuticals, Inc.	2007-07-16	2015-08-31
Azasite	Solution / drops	10 mg/1mL	Ophthalmic	Thea Pharma Inc.	2022-11-01	Not applicable
Azasite	Solution	1 % w/w	Ophthalmic	Inspire Pharmaceuticals, Inc.	Not applicable	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ag-azithromycin	Tablet	600 mg	Oral	Angita Pharma Inc.	2018-09-26	Not applicable
Ag-azithromycin	Tablet	250 mg	Oral	Angita Pharma Inc.	2018-09-26	Not applicable
Apo-azithromycin	Capsule	250 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-azithromycin	Tablet	250 mg	Oral	Apotex Corporation	2005-11-02	Not applicable
Apo-azithromycin Z	Tablet	250 mg	Oral	Apotex Corporation	2014-03-06	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Azithromycin Dihydrate	Azithromycin dihydrate (500 mg/1)	Tablet, coated	Oral	Lannett Company, Inc.	2020-04-18	Not applicable
Zithromax	Azithromycin dihydrate (250 mg/1)	Tablet, film coated	Oral	Pfizer Laboratories Div Pfizer Inc	2020-04-30	Not applicable

Categories

ATC Codes

J01RA07 — Azithromycin, fluconazole and secnidazole

• J01RA — Combinations of antibacterials
• J01R — COMBINATIONS OF ANTIBACTERIALS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

S01AA26 — Azithromycin

• S01AA — Antibiotics
• S01A — ANTIINFECTIVES
• S01 — OPHTHALMOLOGICALS
• S — SENSORY ORGANS

J01FA10 — Azithromycin

• J01FA — Macrolides
• J01F — MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J01RA16 — Cefixime and azithromycin

• J01RA — Combinations of antibacterials
• J01R — COMBINATIONS OF ANTIBACTERIALS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-Bacterial Agents
• Anti-Infective Agents
• Antibacterials for Systemic Use
• Antiinfectives for Systemic Use
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs causing inadvertant photosensitivity
• Experimental Unapproved Treatments for COVID-19
• Lactones
• Macrolide Antimicrobial
• Macrolides
• Macrolides, Lincosamides and Streptogramins
• Moderate Risk QTc-Prolonging Agents
• Ophthalmologicals
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Photosensitizing Agents
• Polyketides
• QTc Prolonging Agents

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 / Lactones / Polyols / Acetals / Oxacyclic compounds / Azacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers / Carbonyl compounds / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds

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Substituents

1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino acid or derivatives / Aminoglycoside core / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Ether / Glycosyl compound / Hydrocarbon derivative / Lactone / Macrolide / Monocarboxylic acid or derivatives / Monosaccharide / O-glycosyl compound / Organic nitrogen compound / Organic oxide / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound / Oxacycle / Oxane / Polyol / Secondary alcohol / Tertiary alcohol / Tertiary aliphatic amine / Tertiary amine

show 22 more

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

macrolide antibiotic (CHEBI:2955)

Affected organisms

• Humans and other mammals

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. [Article]
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. [Article]
3. McMullan BJ, Mostaghim M: Prescribing azithromycin. Aust Prescr. 2015 Jun;38(3):87-9. Epub 2015 Jun 1. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
8. Singlas E: [Clinical pharmacokinetics of azithromycin]. Pathol Biol (Paris). 1995 Jun;43(6):505-11. [Article]
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. [Article]
10. Zithromax FDA label [File]
11. Azithromycin, Ophthalmic FDA label [File]
12. Sandoz Azithromycin Canadian Monograph [File]

External Links

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

PDB Entries

1m1k / 1nwy / 1yhq / 4v7y / 5igi / 5igv / 5uxc / 5uxd / 7w1a / 8e42 …

show 2 more

MSDS

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Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Stillbirths and Infant Mortality	1
4	Active Not Recruiting	Treatment	Co-Infection / Death / Diarrhea / Malaria / Malnutrition / Pneumonia	1
4	Active Not Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / Trachoma	1
4	Completed	Not Available	Healthy Subjects (HS)	1
4	Completed	Basic Science	Microbial Colonization	1

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

Form	Route	Strength
Powder, for solution	Oral	4 g
Tablet	Oral	524.000 mg
Tablet, film coated	Oral	250 mg
Powder, for suspension	Oral	400000 g
Solution	Ophthalmic	1 % w/w
Solution	Ophthalmic	10 mg/1mL
Solution / drops	Ophthalmic	10 mg/1mL
Tablet, film coated	Oral	500 mg
Syrup	Oral	200 MG/5ML
Tablet	Oral	524.100 mg
Powder	Parenteral	200 MG/5ML
Tablet, coated	Oral	500 mg
Injection, powder, for solution	Parenteral
Injection, powder, lyophilized, for solution	Intravenous
Capsule	Oral
For suspension	Oral	100 mg/5mL
For suspension	Oral	200 mg/5mL
Injection	Intravenous	2.5 g/23mL
Injection	Intravenous	500 mg/4.8mL
Injection	Intravenous	500 mg/10mL
Injection, powder, for solution	Intravenous
Injection, powder, lyophilized, for solution	Intravenous	100 mg/1mL
Injection, powder, lyophilized, for solution	Intravenous	500 mg/1
Injection, powder, lyophilized, for solution	Intravenous	500 mg/5mL
Powder, for solution	Oral	200 mg / 5 mL
Powder, for suspension	Oral	1 g/1
Powder, for suspension	Oral	100 mg/5mL
Powder, for suspension	Oral	1200 mg/30mL
Powder, for suspension	Oral	200 mg/5mL
Powder, for suspension	Oral	200 mg / 5 mL
Powder, for suspension	Oral	900 mg/22.5mL
Powder, for suspension	Parenteral	200 mg/5mL
Suspension	Oral	200 mg/5mL
Tablet, film coated	Oral	250 mg/1
Tablet, film coated	Oral	500 mg/1
Tablet, film coated	Oral	600 mg/1
Powder, for suspension	Oral
Syrup	Oral
Tablet, coated	Oral	500 mg/1
Tablet, film coated	Oral	524.1 Mg
Tablet, film coated	Oral	530 MG
Injection, powder, for solution	Parenteral	500 mg
Injection, powder, for solution		500 mg/1vial
Injection, powder, for solution	Intravenous	500.00 mg
Injection, powder, lyophilized, for solution	Intravenous	500 mg/10mL
Tablet	Oral	250 mg/1
Tablet	Oral	500 mg/1
Tablet	Oral	600 mg/1
Powder	Oral
Powder	Parenteral	5 ML
Powder	Parenteral	200 MG
Injection, powder, lyophilized, for solution	Intravenous	500 mg
Tablet	Oral	500.00 mg
Tablet	Oral	50000000 mg
Suspension	Oral	4 g
Powder, for suspension	Oral	4.286 g
Capsule, coated	Oral	500 mg
Powder, for suspension	Oral	40 MG/ML
Powder, for solution		500 MG
Powder, for suspension	Oral	100 MG
Powder, for suspension	Oral	150 MG
Powder, for suspension	Oral	200 MG
Powder, for suspension	Oral	300 MG
Powder, for suspension	Oral	400 MG
Powder, for solution
Injection, powder, for solution	Intravenous	0.5 g
Injection, powder, for solution		500 mg
Tablet, coated	Oral	528.5 mg
Injection, powder, for suspension	Oral	200 mg
Suspension	Oral
Solution	Ophthalmic	3.575 mg
Powder, for solution	Parenteral	500 MG
Solution / drops	Ophthalmic
Solution / drops	Ophthalmic	15 mg/g
Powder, for suspension	Oral	40 g
Solution	Ophthalmic	14.300 mg
Solution	Ophthalmic; Topical	14.3 mg
Tablet, film coated	Oral	524 Mg
Tablet, film coated	Oral	250.00 mg
Injection, powder, for solution
Suspension	Oral	0.90000 g
Suspension	Oral	1500 g
Solution	Intravenous
Suspension	Oral	1200.000 mg
Tablet	Oral	500.000 mg
Tablet	Oral	500 mg
Solution	Ophthalmic	15 mg
Capsule	Oral	250 MG
Suspension	Oral	4 mg
Tablet	Oral	250 mg
Tablet	Oral	600 mg
Powder, for suspension	Oral	600 MG
Capsule	Oral	500.000 mg
Drug delivery system	Oral	4 g
Tablet	Oral
Powder, for solution	Oral	5 g
Powder, for suspension	Oral	4 g
Tablet, coated	Oral	25000000 mg
Tablet, film coated	Oral	530000 MG
Powder	Oral	40 MG/ml
Powder, for solution	Intravenous	500 MG
Tablet, coated	Oral	600 MG
Tablet, coated	Oral	1000 mg
Injection	Intravenous
Syrup	Oral	100 MG
Syrup	Oral	50 MG
Injection, powder, lyophilized, for solution	Parenteral	500 mg
Powder		500 mg
Tablet	Oral
Powder, for suspension	Oral	100 mg / 5 mL
Powder	Oral	100 mg/1sachet
Tablet, coated	Oral	250 mg
Powder, for solution	Oral	200 mg/5ml
Powder, for solution	Intravenous	500 mg / vial
Injection, powder, for solution	Intravenous	100 mg/ml
Tablet, film coated	Oral	600 mg
Injection, powder, for solution	Intravenous	500 mg/1vial
Tablet, coated	Oral	50000000 mg
Granule, for suspension	Oral	2 G
Injection, powder, for solution	Intravenous	500 mg
Powder, for suspension	Oral	2 g/60mL
Granule, for suspension, extended release	Oral	2.096 g/bottle
Granule, for suspension, extended release	Oral	2 g / bottle
Tablet, film coated	Oral
Solution	Ophthalmic	3.750 mg
Powder		500 mg/1vial

Prices

Unit description	Cost	Unit
Zithromax 3 1 gm Packets Box	118.26USD	box
Azithromycin 2.5 gm bulk vial	75.6USD	each
Zmax adult-ped 2 g/60 ml susp	70.39USD	each
Zithromax Tri-Pak 3 500 mg tablet Disp Pack	69.67USD	disp
Zithromax Z-Pak 6 250 mg tablet Disp Pack	68.62USD	disp
Zmax 2 g/60 ml susp sr	67.04USD	each
Zmax pediatric 2 g/60 ml susp	67.04USD	each
Zithromax 200 mg/5ml Suspension 30ml Bottle	52.0USD	bottle
Zithromax 100 mg/5ml Suspension 15ml Bottle	51.6USD	bottle
Zithromax 200 mg/5ml Suspension 15ml Bottle	50.46USD	bottle
Zithromax 200 mg/5ml Suspension 22.5ml Bottle	50.46USD	bottle
Azithromycin 3 500 mg tablet Disp Pack	48.52USD	disp
Azithromycin 6 250 mg tablet Disp Pack	48.52USD	disp
Azasite 1% eye drops	42.85USD	ml
Zithromax i.v. 500 mg vial	34.39USD	vial
Azithromycin 200 mg/5ml Suspension 15ml Bottle	34.25USD	bottle
Zithromax 600 mg tablet	27.22USD	tablet
Zithromax 500 mg tablet	22.68USD	tablet
Zithromax tri-pak 500 mg tablet	22.24USD	tablet
Azithromycin 600 mg tablet	19.04USD	tablet
Azithromycin 500 mg tablet	15.87USD	tablet
Trimox 125 mg/5ml Suspension 100ml Bottle	11.99USD	bottle
Trimox 125 mg/5ml Suspension 150ml Bottle	11.99USD	bottle
Trimox 250 mg/5ml Suspension 80ml Bottle	11.99USD	bottle
Zithromax 250 mg z-pak tablet	11.12USD	tablet
Azithromycin i.v. 500 mg vial	11.09USD	each
Azithromycin powder	10.89USD	g
Zithromax 250 mg tablet	9.41USD	tablet
Azithromycin 250 mg tablet	6.33USD	tablet
Apo-Azithromycin 250 mg Tablet	3.11USD	tablet
Co Azithromycin 250 mg Tablet	3.11USD	tablet
Mylan-Azithromycin 250 mg Tablet	3.11USD	tablet
Novo-Azithromycin 250 mg Tablet	3.11USD	tablet
Phl-Azithromycin 250 mg Tablet	3.11USD	tablet
Pms-Azithromycin 250 mg Tablet	3.11USD	tablet
Ratio-Azithromycin 250 mg Tablet	3.11USD	tablet
Sandoz Azithromycin 250 mg Tablet	3.11USD	tablet
Zithromax 40 mg/ml Suspension	1.7USD	ml
Zithromax 20 mg/ml Suspension	1.2USD	ml
Novo-Azithromycin 40 mg/ml Suspension	0.95USD	ml
Pms-Azithromycin 40 mg/ml Suspension	0.95USD	ml
Sandoz Azithromycin 40 mg/ml Suspension	0.95USD	ml
Novo-Azithromycin 20 mg/ml Suspension	0.67USD	ml
Pms-Azithromycin 20 mg/ml Suspension	0.67USD	ml
Sandoz Azithromycin 20 mg/ml Suspension	0.67USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5192535	No	1993-03-09	2010-03-09
CA2467611	No	2010-03-30	2024-05-18
CA2148071	No	2000-10-17	2015-04-27
US6984403	No	2006-01-10	2024-02-14
US7887844	No	2011-02-15	2024-02-14
US6268489	No	2001-07-31	2018-07-31
US6068859	No	2000-05-30	2017-05-30
US6159458	No	2000-12-12	2017-11-04
US6239113	No	2001-05-29	2019-03-31
US6569443	No	2003-05-27	2019-03-31
US6861411	No	2005-03-01	2018-11-25
US7056893	No	2006-06-06	2019-03-31

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	126	http://www.chemspider.com/Chemical-Structure.2298410.html
water solubility	soluble in ethanol and DSMO, minimally soluble in water	https://www.caymanchem.com/pdfs/15004.pdf
logP	3.03	http://www.medicines.org.au/files/afpazith.pdf
pKa	8.5	https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0174372

Predicted Properties

Property	Value	Source
Water Solubility	0.514 mg/mL	ALOGPS
logP	3.03	ALOGPS
logP	2.44	Chemaxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.43	Chemaxon
pKa (Strongest Basic)	9.57	Chemaxon
Physiological Charge	2	Chemaxon
Hydrogen Acceptor Count	13	Chemaxon
Hydrogen Donor Count	5	Chemaxon
Polar Surface Area	180.08 Å2	Chemaxon
Rotatable Bond Count	7	Chemaxon
Refractivity	194.11 m3·mol-1	Chemaxon
Polarizability	82.93 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.5518
Blood Brain Barrier	-	0.9739
Caco-2 permeable	-	0.7578
P-glycoprotein substrate	Substrate	0.8765
P-glycoprotein inhibitor I	Inhibitor	0.8513
P-glycoprotein inhibitor II	Non-inhibitor	0.8893
Renal organic cation transporter	Non-inhibitor	0.8753
CYP450 2C9 substrate	Non-substrate	0.8373
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.6403
CYP450 1A2 substrate	Non-inhibitor	0.9295
CYP450 2C9 inhibitor	Non-inhibitor	0.9021
CYP450 2D6 inhibitor	Non-inhibitor	0.8904
CYP450 2C19 inhibitor	Non-inhibitor	0.9023
CYP450 3A4 inhibitor	Non-inhibitor	0.9533
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9751
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.9397
Biodegradation	Not ready biodegradable	0.9673
Rat acute toxicity	2.5423 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9929
hERG inhibition (predictor II)	Non-inhibitor	0.8555

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001i-9400002500-41dea9c95a10a1b1de40
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0f6t-0300030900-1a7ea512a0aa566e59ed
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-066r-4911100000-f759f24274aebce8e08c
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-052f-3912280200-df9a72a4769570064ef9
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004l-0309050000-5e1be028a242f0d384eb
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0f6t-0300030900-1a7ea512a0aa566e59ed
MS/MS Spectrum - , positive	LC-MS/MS	splash10-066r-4911100000-f759f24274aebce8e08c
MS/MS Spectrum - , positive	LC-MS/MS	splash10-052f-3912280200-df9a72a4769570064ef9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-0000020900-42f3620d45c59fa6ed61
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-0000020900-4413a5a5fc56819e2562
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00fr-2900061500-1126e34f117078f0ca50
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00dj-2900021700-42c55d7fb169e699bfb4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0bt9-5900011000-e1fef15d602a7e419f18
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-1900022300-3b6c35f6ee6b99ff542b

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	279.849668	predicted	DarkChem Lite v0.1.0
[M-H]-	274.323668	predicted	DarkChem Lite v0.1.0
[M-H]-	263.98578	predicted	DeepCCS 1.0 (2019)
[M+H]+	273.269768	predicted	DarkChem Lite v0.1.0
[M+H]+	265.672868	predicted	DarkChem Lite v0.1.0
[M+H]+	265.7095	predicted	DeepCCS 1.0 (2019)
[M+Na]+	274.066068	predicted	DarkChem Lite v0.1.0
[M+Na]+	272.0013	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. 23S ribosomal RNA

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. [Article]
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. [Article]
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. [Article]
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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>10000000	N/A	N/A	A18346

Details

Binding Properties2. Protein-arginine deiminase type-4

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. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54