Azithromycin

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H317：Kann allergische Hautreaktionen verursachen.

  H334：Kann bei Einatmen Allergie, asthmaartige Symptome oder Atembeschwerden verursachen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P342+P311：Bei Symptomen der Atemwege: GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

Azithromycin Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  Azithromycin was the first of the azalides and was designed to improve the stability and biological half-life of erythromycin A, as well as improve activity against Gram negative bacteria. Azithromycin is a long-acting macrolide antibiotic structurally related to erythromycin A (EA), having a methyl-substituted nitrogen at position 9a in the aglycone ring.

• Chemische Eigenschaften

  White Crystalline Powder

• Originator

  Pliva (Yugoslavia)

• Verwenden

  Azithromycin is an azalide macrolide antibiotic.

• Definition

  ChEBI: Azithromycin is a macrolide antibiotic useful for the treatment of bacterial infections. It is an azalide, derived from erythromycin, and a member of a subclass of macrolide antibiotics with bacteriocidal and bacteriostatic activities.

• Indications

  Azithromycin in a 500-mg dose three times a week has been shown to yield a 60% reduction in inflammatory papules in 83% of patients enrolled in a 12- week study. There is no associated pseudotumor cerebri and, therefore, it can be used for an acne flare during early Accutane therapy.

• Manufacturing Process

  To a solution of 0.54 g (0.000722 mole) of 11 aza-10-deoxo-10- dihydroerythromycin A in 20 ml CHCl3 were added 0.0589 ml (0.000741 mole) of formaldehyde (approx. 35% w./w.) and 0.00283 g (0.000735 mole) of formic acid (approx. 98 to 100% w./w.). The reaction mixture was stirred for 8 hours while heating under reflux, then cooled to ambient temperature, whereupon were added 15 ml of water (pH 5.8). The pH of the reaction mixture was adjusted to 5.0 by means of 2 N HCl, whereupon the CHCl3 layer was separated. To the aqueous part was added 15 ml of CHCl3, the pH of the reaction suspension was adjusted to 7.5 by means of 20% NaOH, the layers were separated and subsequently the aqueous layer was extracted three times with 15 ml of CHCl3. The combined chloroform extracts having pH 7.5 were dried over K2CO3 and evaporated under reduced pressure, yielding 0.45 g (82.4%) of N-methyl-11-aza-10-deoxo-10-dihydro erythromycin A (azithromycin), m.p. 113°-115°C. [α]D 20= - 37.0 (1% in CHCl3).

• Trademarks

  Zithromax (Pfizer); Zmax (Pfizer);Sunamed.

• Therapeutic Function

  Antibiotic

• Antimicrobial activity

  It is less potent than erythromycin A against Gram-positive isolates, but is more active against Gram-negative bacteria. It is four times more potent than erythromycin A against H. influenzae, N. gonorrhoeae and Campylobacter spp., and twice as active against Mor. catarrhalis. It also exhibits superior potency against Enterobacteriaceae, notably Esch. coli, Salmonella enterica serotypes, and Shigella spp. It is active against Mycobacteria, notably the M. avium complex and against intracellular micro-organisms such as Legionella and Chlamydia spp.
  Chemical modification at the 9 position of the erythronolide A ring of erythromycin A blocks the internal ketalization and markedly improves acid stability. At pH 2, loss of 10% activity occurred in less than 4 s with erythromycin A, but took 20 min with azithromycin. The AUC at 0–24 h is 4.5 mg.h/L. The level is only slightly increased on repeated dosing.
  Binding to plasma protein varies with the concentration, from around 50% at 0.05 mg/L to 7.1% at 1 mg/L. The apparent elimination half-life is dependent upon sampling interval: between 8 and 24 h it ranged from 11 to 14 h; between 24 and 72 h it was 35–40 h.
  It rapidly penetrates the tissues, reaching levels that approach or, in some cases, exceed the simultaneous plasma levels and persist for 2–3 days. Only about 6% of the dose is found in urine in the first 24 h.

• Allgemeine Beschreibung

  The spectrum of antimicrobial activity of azithromycin issimilar to that observed for erythromycin and clarithromycinbut with some interesting differences. In general,it is more active against Gram-negative bacteria and less activeagainst Gram-positive bacteria than its close relatives.The greater activity of azithromycin against H. influenzae,M. catarrhalis, and M. pneumoniae coupled with its extendedhalf-life permits a 5-day dosing schedule for thetreatment of respiratory tract infections caused by thesepathogens. The clinical efficacy of azithromycin in the treatmentof urogenital and other sexually transmitted infectionscaused by Chlamydia trachomatis, N. gonorrhoeae, H.ducreyi, and Ureaplasma urealyticum suggests that singledosetherapy with it for uncomplicated urethritis or cervicitismay have advantages over use of other antibiotics.

• Biologische Aktivität

  Azithromycin is a macrolide antibiotic. It is active against S. pneumoniae, S. aureus, N. gonorrhoeae, M. pneumoniae, H. pylori, C. trachomatis, and H. influenzae in vitro (MIC90s = <0.01-2 mg/L). Azithromycin increases survival in mouse models of intraperitoneal S. pyogenes, S. pneumoniae, E. faecalis, or H. influenzae infection (ED50s = 0.78, 8.7, 12.7, and 30.3 mg/kg, respectively). It inhibits replication of severe acute respiratory coronavirus 2 (SARS-CoV-2), but not Middle East respiratory syndrome CoV (MERS-CoV), when used at concentrations of 5 and 10 μM. Azithromycin also decreases plasma levels of IL-6, TNF-α, and IL-1β and increases survival in a mouse model of LPS-induced sepsis when administered at a dose of 100 mg/kg. Formulations containing azithromycin have been used in the treatment of a variety of bacterial infections.

• Pharmakokinetik

  Oral absorption：37%
  Cmax 250 mg oral： 0.17 mg/L after 2.2 h
  500 mg oral： 0.4 mg/L after2h
  Plasma half-life (terminal)： 11–40 h
  Volume of distribution： 31 L/kg
  Plasma protein binding ：7–50%
  Chemical modification at the 9 position of the erythronolide A ring of erythromycin A blocks the internal ketalization and markedly improves acid stability. At pH 2, loss of 10% activity occurred in less than 4 s with erythromycin A, but took 20 min with azithromycin. The AUC at 0–24 h is 4.5 mg.h/L. The level is only slightly increased on repeated dosing.
  Binding to plasma protein varies with the concentration, from around 50% at 0.05 mg/L to 7.1% at 1 mg/L. The apparent elimination half-life is dependent upon sampling interval: between 8 and 24 h it ranged from 11 to 14 h： between 24 and 72 h it was 35–40 h.
  It rapidly penetrates the tissues, reaching levels that approach or, in some cases, exceed the simultaneous plasma levels and persist for 2–3 days. Only about 6% of the dose is found in urine in the first 24 h.

• Clinical Use

  This product is suitable for the treatment of the following symptoms of infection caused by susceptible bacteria:
  1. For acute pharyngitis and acute tonsillitis caused by Streptococcus pyogenes and for nasosinusitis, acute otitis media, acute bronchitis, and acute exacerbation of chronic bronchitis caused by sensitive bacteria.
  2. For pneumonia caused by Mycoplasma pneumonia, Streptococcus pneumonia and Haemophilus influenza.
  3. For urethritis, cervicitis and pelvic inflammatory disease caused by chlamydia and non-multiple drug resistance Neisseria gonorrhoeae, and for simple genital infection caused by non-multiple drug resistance Neisseria gonorrhoeae (exclude co-infection of Misu spirochetes).
  4. For skin and soft tissue infections caused by sensitive bacteria.

• Nebenwirkungen

  Azithromycin is well tolerated with little gastrointestinal disturbance.

• Veterinary Drugs and Treatments

  Azithromycin with its relative broad spectrum and favorable pharmacokinetic profile may be useful for a variety of infections in veterinary species. Little data is published at this time, however. Azithromycin has been shown to be ineffective in the treatment of Mycoplasma haemofelis in cats.
  Azithromycin may be potentially useful for treating Rhodococcus infections in foals.

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Anti-arrhythmics: increased toxicity with disopyramide; increased risk of ventricular arrhythmias with dronedarone - avoid.
  Antibacterials: possibly increased rifabutin concentration (increased risk of uveitis and neutropenia) - reduce dose of rifabutin.
  Anticoagulants: effect of coumarins may be enhanced.
  Antidepressants: the manufacturer of reboxetine advises to avoid concomitant use.
  Antihistamines: may inhibit the metabolism of mizolastine (risk of hazardous arrhythmias) - avoid.
  Antimalarials: avoid with artemether/lumefantrine; increased risk of ventricular arrhythmias with piperaquine with artenimol - avoid.
  Antipsychotics: increased risk of ventricular arrhythmias with droperidol - avoid.
  Antivirals: concentration possibly increased by ritonavir.
  Ciclosporin: may inhibit the metabolism of ciclosporin (increased ciclosporin levels).
  Colchicine: treatment with both agents has been shown in a study to increase the risk of fatal colchicine toxicity, especially in patients with renal impairment - avoid.
  Ergot alkaloids: increased risk of ergotism - avoid.
  Statins: possible increased risk of myopathy with atorvastatin and simvastatin.

• Stoffwechsel

  In pharmacokinetic studies it has been demonstrated that the concentrations of azithromycin measured in tissues are noticeably higher (as much as 50 times) than those measured in plasma, which indicates that the agent strongly binds to tissues. Azithromycin is excreted in bile mainly as unchanged drug. Ten metabolites have also been detected in bile, which are formed through N- and O- demethylation in the liver, hydroxylation of desosamine - and aglycone rings and cleavage of cladinose conjugate. The metabolites of azithromycin are not microbiologically active

• Lager

  -20°C

• Mode of action

  Azithromycin reversibly binds to the 50S ribosomal subunit of the 70S ribosome of sensitive microorganisms, thereby inhibiting the translocation step of protein synthesis, wherein a newly synthesized peptidyl tRNA molecule moves from the acceptor site on the ribosome to the peptidyl (donor) site, and consequently inhibiting RNA-dependent protein synthesis leading to cell growth inhibition and cell death.

Azithromycin Upstream-Materialien And Downstream Produkte

Azithromycin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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