Azithromycin
- Atc Codes:J01FA10#S01AA26
- CAS Codes:83905-01-5#121479-24-4#117772-70-0
- PHARMGKB ID:83905-01-5#121479-24-4#117772-70-0
Table of contents
- Brand Names
- Drug Combinations
- Chemistry
- Pharmacologic Category
- Mechanism of Action
- Therapeutic Use
- Unlabeled Use
- Pregnancy and Lactation Implications
- Contraindications
- Warnings and Precautions
- Adverse Reactions
- Caution and personalized dose adjustment in patients with the following genotypes
- Substrate of
- Inhibits
- Drug Interactions
- Nutrition/Nutraceutical Interactions
- Dosage
- Pharmacokinetics and Pharmacodynamics
- Special Considerations
Brand Names
Europe
Austria: Azithromycin, Azithrostad, Azyter, Zithromax; Belgium: Azithromycine, Zitromax; Bulgaria: Azatril, Azax, Azibiot, Binozyt, Sumamed, Zmax; Cyprus: Zithromax; Czech Republic: Azibiot, Azithromycin, Azitromycin, Azitrox, Sumamed, Zetamac, Zitrocin; Denmark: Azithromycin, Zitromax; Estonia: Azatril, Azimepha, Azithromycin, Azitrox, Sumamed, Zitraval; Finland: Azithromycin, Zithromax; France: Azadose, Azithromycine, Azyter, Zithromax; Germany: Azithexal, Azithro, Azithrobeta, Azithromycin, Azyter, Ultreon, Zithromax, Zitromax; Greece: Azibactron, Azibiom, Azifarm, Azirox, Azirutec, Azithral, Azithrin, Azithromycin, Azitrolid, Azivirus, Azytan, Bezanin, Binozyt, Disithrom, Figothrom, Flumax, Goldamycin, Gramokil, Novozithron, Razimax, Thoraxx, Zinfect, Zithro-Due, Zithrobest, Zithromax, Zithromil, Zithroplus, Zithrotel, Zithroxyn, Zitrax, Zyramycin; Hungary: Azi, Azibiot, Azithromycin, Makromycin, Sumamed, Zitrocin, Zmax; Ireland: Azithromycin, Zithromax; Italy: Aziprome, Azitrocin, Azitroerre, Azitromicina, Batif, Ribotrex, Tetris, Trozocina, Zitrobiotic, Zitromax; Latvia: Azimepha, Azithromycin, Sumamed, Zitraval; Lithuania: Azithromycin; Malta: Azithrin, Azithromycin, Zithromax; Netherlands: Azitromycine, Zithromax; Poland: Azibiot, Azimycin, AziTeva, Azithromycin, Azitrin, Azitro, Azitrox, Azycyna, Azyter, Bactrazol, Macromax, Nobaxin, Oranex, Rozalin, Sumamed, Zetamax; Portugal: Azitromicina; Slovakia: Azatril, Azibiot, Azitromicina, Azitrox, Origen, Sumamed, Zitrocin, Zmax; Slovenia: Azibiot, Azitromicin, Sumamed, Zitraval, Zitrocin; Spain: Aratro, Azitromicina, Azydrop, Vinzam, Zentavión, Zitromax; Sweden: Azithromycin, Azitromax; UK: Azithromycin, Zithromax.
North America
Canada: Azithromycin, Zithromax; USA: Azasite, Azithromycin, Zithromax, Zmax.
Latin America
Argentina: Arzomicín, Azibiotic, Azitral, Azitrogal, Azitrolán, Azitromicina, Azitrox, Cetaxim, Clearsing, Cronopen, Doyle, Fabramicina, Macromax, Misultina, Naxocina, Neblic, Nifostín, Novozitrón, Orobiotic, Sitrox, Talcilina, Tanezox, Triamid, Tritab, Vectocilina, Visag, Zitromax; Brazil: Astro, Atromicin, Azalide, Azatill, Azi, Azimed, Azimix, Azinostil, Azitrin, Azitrogran, Azitrolab, Azitromicil, Azitromicina, Azitron, Azitrophar, Azitroxil, Clindal, Ems-Max, Mac Azi, Mazitrom, Novatrex, Selimax, Tromix, Trozyman, Zidimax, Zitromax, Zitromil, Zitroneo; Mexico: Atoxitom, Azibiot, Azidral, Aziphar, Aziteva, Azitrocin, Azitromicina, Azo-Max, Charyn, Koptin, Macrozit, Marzivag, Medatz, Sicalan, Texis, Tromicina, Truxa, Zertalin, Zithran, Zitroken.
Asia
Japan: Zithromac.
Drug combinations
Azithromycin and Nimesulide
Chemistry
Azithromycin: C~38~H~72~N~2~O~12~ xH~2~O. Mw: 748.98 (anhydrous). (1) 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, [2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-; (2)(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one; (3) 9-Deoxo-9a-aza-9a-methyl-9a-homoerythromycin A. CAS-83905-01-5 (anhydrous); CAS-121479-24-4 (monohydrate); CAS-117772-70-0 (dihydrate)(1987).
Pharmacologic Category
Antibacterials; Other Macrolides. (ATC-Code: J01FA10; S01AA26).
Mechanism of action
Inhibits RNA-dependent protein synthesis at the chain elongation step.
Therapeutic use
Treatment of acute otitis media due to H. influenzae, M. catarrhalis, or S. pneumoniae. Pharyngitis/tonsillitis due to S. pyogenes. Treatment of upper and lower respiratory tract infections, infections of the skin and skin structure, community-acquired pneumonia, pelvic inflammatory disease, sexually-transmitted diseases (urethritis/cervicitis), pharyngitis/tonsillitis and genital ulcer disease (chancroid) due to susceptible strains of C. trachomatis, M. catarrhalis, H. influenzae, S. aureus, S. pneumoniae, Mycoplasma pneumoniae, and C. psittaci. Acute bacterial exacerbations of chronic obstructive pulmonary disease due to H. influenzae, M. catarrhalis, or S. pneumoniae. Acute bacterial sinusitis. Bacterial conjunctivitis.
Pregnancy and lactiation implications
Adverse events were not observed in animal studies. Low levels of azithromycin cross the placenta. Azithromycin may be used for the treatment of some infections during pregnancy. Azithromycin is excreted in low amounts into breast milk. Use with caution during lactation.
Unlabeled use
Mycobacterium avium complex in advanced HIV infection. Infective endocarditis. Pertussis.
Contraindications
Hypersensitivity to azithromycin, other macrolide antibiotics, or any component of the formulation.
Warnings and precautions
Use with caution in risk of prolonged cardiac repolarization (QTc prolongation and ventricular arrhythmias, including torsade de pointes may occur). Prolonged use may result in fungal or bacterial superinfection, including C. difficile-associated diarrhea and pseudomembranous colitis. May mask or delay symptoms of incubating gonorrhea or syphilis. Use with caution in pre-existing liver disease, (risk of hepatic impairment, including hepatocellular and/or cholestatic hepatitis, with or without jaundice), or in severe renal impairment (CrCl <10 mL/minute). Ophthalmic solution contains benzalkonium chloride. Eye drops should not be injected subconjunctivally or introduced directly into the anterior chamber of the eye.