pharmacopeia

Azithromycin

AntibioticsMacrolidesMacrolide AntimicrobialProtein Synthesis InhibitorsDecreased Protein SynthesisUS-FDASourced from openFDAOrange Book · AB · generic
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/api/v1/drug/azithromycin
2D structure
(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]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O
InChIKey MQTOSJVFKKJCRP-BICOPXKESA-N

Mechanism of action

Sourced from openFDA

Azithromycin is a macrolide antibacterial drug.

Protein Synthesis

Indications

Sourced from openFDA
  • Azithromycin is a macrolide antibacterial drug indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions listed below. Recommended dosages and durations of therapy in adult and pediatric patient populations vary in these indications.

Contraindications

Sourced from openFDA
  • • Patients with known hypersensitivity to azithromycin, erythromycin, any macrolide or ketolide drug. () • Patients with a history of cholestatic jaundice/hepatic dysfunction associated with prior use of azithromycin.contraindicated

Dosage & administration

Sourced from openFDA

• Adult Patients ( ) Infection Recommended Dose/Duration of Therapy Community-acquired pneumonia (mild severity) Pharyngitis/tonsillitis (second-line therapy) Skin/skin structure (uncomplicated) 500 mg as a single dose on Day 1, followed by 250 mg once daily on Days 2 through 5. Acute bacterial exacerbations of chronic bronchitis (mild to moderate) 500 mg as a single dose on Day 1, followed by 250 mg once daily on Days 2 through 5 or 500 mg once daily for 3 days. Acute bacterial sinusitis 500 mg once daily for 3 days. Genital ulcer disease (chancroid) Non-gonococcal urethritis and cervicitis One single 1 gram dose. Gonococcal urethritis and cervicitis One single 2 gram dose. • Pediatric Patients ( ) Infection Recommended Dose/Duration of Therapy Acute otitis media (6 months of age and older) 30 mg/kg as a single dose or 10 mg/kg once daily for 3 days or 10 mg/kg as a single dose on Day 1 followed by 5 mg/kg/day on Days 2 through 5. Acute bacterial sinusitis (6 months of age and older) 10 mg/kg once daily for 3 days. Community-acquired pneumonia (6 months of age and older) 10 mg/kg as a single dose on Day 1 followed by 5 mg/kg once daily on Days 2 through 5. Pharyngitis/tonsillitis (2 years of age and older) 12 mg/kg once daily for 5 days.

Warnings & precautions

Sourced from openFDA

• Serious (including fatal) allergic and skin reactions: Discontinue azithromycin if reaction occurs. () • Hepatotoxicity: Severe, and sometimes fatal, hepatotoxicity has been reported. Discontinue azithromycin immediately if signs and symptoms of hepatitis occur. () • Infantile Hypertrophic Pyloric Stenosis (IHPS): Following the use of azithromycin in neonates (treatment up to 42 days of life), IHPS has been reported. Direct parents and caregivers to contact their physician if vomiting or irritability with feeding occurs. () • Prolongation of QT interval and cases of torsades de pointes have been reported. This risk which can be fatal should be considered in patients with certain cardiovascular disorders including known QT prolongation or history torsades de pointes, those with proarrhythmic conditions, and with other drugs that prolong the QT interval. ( 5.4 ) • Cardiovascular Death: Some observational studies have shown an approximately two-fold increased short-term potential risk of acute cardiovascular death in adults exposed to azithromycin relative to other antibacterial drugs, including amoxicillin. Consider balancing this potential risk with treatment benefits when prescribing azithromycin. () • Clostridioides difficile -Associated Diarrhea: Evaluate patients if diarrhea occurs. () • Azithromycin may exacerbate muscle weakness in persons with myasthenia gravis.

Adverse reactions

Sourced from openFDA

The following clinically significant adverse reactions are described elsewhere in labeling: • Hypersensitivity [see ] • Hepatotoxicity [see ] • Infantile Hypertrophic Pyloric Stenosis (IHPS) [see ] • QT Prolongation [see Warnings and Precautions (5.4) ] • Cardiovascular Death [see ] • Clostridioides difficile- Associated Diarrhea (CDAD) [see ] • Exacerbation of Myasthenia Gravis [see ] Most common adverse reactions are diarrhea (5 to 14%), nausea (3 to 18%), abdominal pain (3 to 7%), or vomiting (2 to 7%). ( ) To report SUSPECTED ADVERSE REACTIONS, contact Aurobindo Pharma USA, Inc. at 1-866-850-2876 or FDA at 1-800-FDA-1088 or www.fda.gov/medwatch. 6.1 Clinical Trials Experience Because clinical trials are conducted under widely varying conditions, adverse reaction rates observed in the clinical trials of a drug cannot be directly compared to rates in the clinical trials of another drug and may not reflect the rates observed in practice. In clinical trials, most of the reported side effects were mild to moderate in severity and were reversible upon discontinuation of the drug. Potentially serious adverse reactions of angioedema and cholestatic jaundice were reported. Approximately 0.7% of the patients (adults and pediatric patients) from the 5-day multiple-dose clinical trials discontinued azithromycin therapy because of treatment-related adverse reactions. In adults given 500 mg/day for 3 days, the discontinuation rate due to treatment-related adverse reactions was 0.6%.

Use in specific populations

Sourced from openFDA

• Pediatric use: Safety and effectiveness in the treatment of patients under 6 months of age have not been established. () • Geriatric use: Elderly patients may be more susceptible to development of torsades de pointes arrhythmias. () 8.1 Pregnancy Risk Summary Available data from published literature and postmarketing experience over several decades with azithromycin use in pregnant women have not identified any drug-associated risks for major birth defects, miscarriage, or adverse maternal or fetal outcomes (see Data) . Developmental toxicity studies with azithromycin in rats, mice, and rabbits showed no drug-induced fetal malformations at doses up to 4, 2, and 2 times, respectively, an adult human daily dose of 500 mg based on body surface area. Decreased viability and delayed development were observed in the offspring of pregnant rats administered azithromycin from day 6 of pregnancy through weaning at a dose equivalent to 4 times an adult human daily dose of 500 mg based on body surface area (see Data) . The estimated background risk of major birth defects and miscarriage for the indicated populations is unknown. All pregnancies have a background risk of birth defect, loss, or other adverse outcomes. In the U.S.

Pharmacokinetics

Sourced from openFDA
Metabolism
Following oral administration of a single 500 mg dose (two 250 mg tablets) to 36 fasted healthy male volunteers, the mean (SD) pharmacokinetic parameters were AUC 0-72 =4.3 (1.2) mcg·hr/mL; C max =0.5 (0.2) mcg/mL; T max =2.2 (0.9) hours. Two azithromycin 250 mg tablets are bioequivalent to a single 500 mg tablet.

Overdosage

Sourced from openFDA

Adverse reactions experienced at higher than recommended doses were similar to those seen at normal doses particularly nausea, diarrhea, and vomiting. In the event of overdosage, general symptomatic and supportive measures are indicated as required.

Approval history

Sourced from openFDA
  • Oct 19, 1995NDANDA050710Pfizer
  • Jul 18, 1996NDANDA050711Pfizer
  • Jan 30, 1997NDANDA050733Pfizer
  • May 24, 2002NDANDA050784Pfizer
  • Nov 14, 2005ANDAANDA065209Sandoz
  • Nov 14, 2005ANDAANDA065211Sandoz
  • Nov 14, 2005ANDAANDA065212Sandoz
  • Apr 27, 2007NDANDA050810Thea Pharma

FDA shortages

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Reference statistics from the openFDA drug-shortage dataset. For a live view, consult the FDA database directly. Not clinical guidance.

  • Azithromycin, Injection, 500 mg Single Dose ADD-Vantage® Glass Vial (NDC 0409-0144-11)To be discontinued
    Sponsor: Hospira, Inc., a Pfizer Company
    Updated
  • Zithromax IV, Injection, 500 mg/5 mL (NDC 0069-3150-83)To be discontinued
    Sponsor: Pfizer Inc.
    Updated
  • Zithromax, Tablet, 250 mg (NDC 0069-4061-01)To be discontinued
    Sponsor: Pfizer Inc.
    Updated
  • Zithromax, Tablet, 500 mg (NDC 0069-3070-30)To be discontinued
    Sponsor: Pfizer Inc.
    Updated

FAERS reports

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Reference statistics only. FAERS reports are voluntarily submitted and are not incidence rates, safety signals, or causal evidence. Counts reflect reporting volume — how often a reaction was reported, not how often it occurs. For decision-grade use, consult openFDA and the FAERS Public Dashboard directly.
58,234 total reports matchedLatest report Share = reports listing the reaction ÷ total matched reports. Rows can sum to >100% because a single report often lists multiple reactions.
  1. 1Off Label Use5,0568.7%
  2. 2Drug Ineffective4,9498.5%
  3. 3Dyspnoea4,5067.7%
  4. 4Nausea3,3685.8%
  5. 5Pain3,2375.6%
  6. 6Pneumonia3,0995.3%
  7. 7Cough3,0215.2%
  8. 8Drug Hypersensitivity2,9645.1%
  9. 9Diarrhoea2,8855.0%
  10. 10Fatigue2,8064.8%
  11. 11Headache2,5404.4%
  12. 12Pyrexia2,3264.0%
  13. 13Vomiting2,2263.8%
  14. 14Anxiety2,2203.8%
  15. 15Asthma2,1193.6%

Literature

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Recent PubMed references pinned to Azithromycin as a MeSH major topic. Citations link to pubmed.ncbi.nlm.nih.gov.

Clinical trials

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The 10 most recently updated of 699 ClinicalTrials.gov registrations naming Azithromycin as an intervention. Registration is not evidence of efficacy or safety — reference crosswalk only.

Structural analogs

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Ranked by 2D fingerprint (Tanimoto) similarity over PubChem structures. Structural proximity only — not a claim of therapeutic equivalence.

Frequently asked questions

How does Azithromycin work?
Azithromycin is a macrolide antibacterial drug.
What is Azithromycin used for?
According to FDA labeling, Azithromycin carries indications including: Azithromycin is a macrolide antibacterial drug indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions listed below. Recommended dosages and durations of therapy in adult and pediatric patient populations vary in these indications.. This is a reference summary of labeled uses, not medical advice or a treatment recommendation.
What class of drug is Azithromycin?
Azithromycin is classified as Antibiotics, Macrolides, Macrolide Antimicrobial, Protein Synthesis Inhibitors, Decreased Protein Synthesis.
What are the brand names for Azithromycin?
Azithromycin is marketed under brand names including AzaSite, Zithromax.
What are the contraindications for Azithromycin?
Azithromycin labeling lists contraindications including: • Patients with known hypersensitivity to azithromycin, erythromycin, any macrolide or ketolide drug. () • Patients with a history of cholestatic jaundice/hepatic dysfunction associated with prior use of azithromycin.. Always consult the full prescribing information and a clinician.
Note. Data for azithromycin is illustrative MVP content compiled from public sources. pharmacopeia is for educational and informational use only and is not a substitute for professional medical advice.

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