molecular formula C38H72N2O12 B1666446 Azithromycin CAS No. 83905-01-5

Azithromycin

Katalognummer: B1666446
CAS-Nummer: 83905-01-5
Molekulargewicht: 749.0 g/mol
InChI-Schlüssel: MQTOSJVFKKJCRP-FHZDSTMTSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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Wirkmechanismus

Azithromycin is a broad-spectrum macrolide antibiotic with a high degree of tissue penetration . It is primarily used for the treatment of respiratory, enteric, and genitourinary infections .

Target of Action

This compound’s primary target is the 23S rRNA of the bacterial 50S ribosomal subunit . This component plays a crucial role in bacterial protein synthesis.

Mode of Action

This compound binds to the 23S rRNA of the bacterial 50S ribosomal subunit . This binding inhibits the transpeptidation/translocation step of protein synthesis and prevents the assembly of the 50S ribosomal subunit . As a result, it stops bacterial protein synthesis, leading to the inhibition of bacterial growth and multiplication .

Biochemical Pathways

This compound disrupts crucial biochemical pathways by binding to specific targets, thereby preventing cell growth and, in the case of bactericidal agents, causing cell death . It inhibits bacterial protein synthesis, quorum-sensing, and reduces the formation of biofilm .

Pharmacokinetics

This compound has a long half-life and a high degree of tissue penetration . Approximately 37% of a single oral dose of 500 mg is bioavailable, producing a peak serum concentration of 0.4 mg/l . It is carried to the site of infection by human phagocytic cells . Biliary excretion of this compound, primarily as unchanged drug, is a major route of elimination .

Result of Action

The result of this compound’s action is the inhibition of bacterial growth and multiplication . By disrupting protein synthesis, it prevents the bacteria from growing and reproducing, which eventually leads to the death of susceptible bacteria .

Action Environment

This compound’s action, efficacy, and stability can be influenced by environmental factors. For instance, it has been found that higher concentrations of this compound are reported in diseased (inflamed) gingiva compared with healthy gingiva . This suggests that using a higher first dose of this compound with an acute infection, when the inflammatory response is most pronounced and phagocytic cells are likely to be most abundant, may result in increased absorption and delivery to an infection site within the first 24 hours, causing greater bacterial clearance .

Biochemische Analyse

Biochemical Properties

Azithromycin is 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 . This allows for the prevention of its metabolism . This compound is a weak substrate for CYP3A4, and is minimally metabolized by the enzyme .

Cellular Effects

This compound is known to have both antiviral and immunomodulatory effects . It interferes with receptor-mediated binding, viral lysosomal escape, intracellular cell-signaling pathways, and enhances type I and III interferon expression . It also disrupts immune and metabolic networks, including down-regulation of mucin production .

Molecular Mechanism

This compound works by decreasing the production of protein, thereby stopping bacterial growth . It binds to the 23S rRNA of the bacterial 50S ribosomal subunit . This inhibits protein synthesis, which is essential for bacterial replication .

Temporal Effects in Laboratory Settings

This compound is used long term for the prevention of exacerbations of bronchiectasis and COPD . The usual dose is 250mg three times a week . It has been demonstrated to maintain this compound concentrations at sites of infection and continues to be effective for several days after administration has ceased .

Dosage Effects in Animal Models

In animal models, the effects of this compound can vary with different dosages . For example, a single oral dose of 10 to 40 mg/kg provided tissue levels that were proportional to the dose in rats . Two- to 4-fold increases in tissue concentration were observed in rats after being dosed with 20 mg/kg for 7 days .

Metabolic Pathways

This compound is associated with a network of altered energy metabolism pathways and immune subsets, including T cells biased toward immunomodulatory and exhausted profiles . In vitro, this compound exposure inhibited T-cell cytotoxicity against tumor cells and impaired T-cell metabolism through glycolysis inhibition .

Transport and Distribution

This compound gains rapid and high concentration in a number of cells including polymorphonuclear leucocytes, monocytes, and macrophages . Extensive and rapid distribution from serum into the intracellular compartments is followed by rapid distribution to the tissues . Tissue concentrations exceed serum concentrations by up to 100-fold following a single this compound 500mg dose .

Subcellular Localization

This compound gains entry into cells by both passive and active transport due to its dibasic amphophilic character . It acts by inhibiting protein biosynthesis at the 50S ribosomal level . Intracellular penetration is greatest in the first 24 hours, but continues for up to 72 hours in human fibroblasts .

Vorbereitungsmethoden

Synthesewege und Reaktionsbedingungen: Azithromycin wird aus Erythromycin A durch eine Reihe chemischer Reaktionen synthetisiert. Der Prozess beinhaltet die Umwandlung von Erythromycin A in sein Oxim, gefolgt von einer Beckmann-Umlagerung, um den Aminoether von Erythromycin A zu bilden. Dieser Zwischenprodukt wird dann zu 9-Deoxo-9a-Aza-9a-Homoerythromycin reduziert, und schließlich führt eine reduktive N-Methylierung zu this compound .

Industrielle Produktionsmethoden: Die industrielle Produktion von this compound beinhaltet häufig die Heißschmelzextrusion, um amorphe Feststoffdispersionen von this compound herzustellen. Diese Methode verbessert die Löslichkeit und Geschmacksmaskierung des Arzneimittels. Die optimalen Extrusionsparameter umfassen eine Temperatur von 150 °C, eine Schneckengeschwindigkeit von 75 U/min und einen Wirkstoffanteil von 25 % .

Vergleich Mit ähnlichen Verbindungen

Azithromycin ist strukturell mit Erythromycin und Clarithromycin verwandt, beides Makrolid-Antibiotika. this compound hat einen 15-gliedrigen Ring mit einem methylsubstituierten Stickstoff, der es vom 14-gliedrigen Lactonring von Erythromycin unterscheidet . Dieser strukturelle Unterschied verleiht this compound eine längere Halbwertszeit und eine bessere Gewebsdurchdringung im Vergleich zu Erythromycin . Andere ähnliche Verbindungen umfassen Clarithromycin und Roxithromycin, die ähnliche Wirkmechanismen aufweisen, sich aber in ihren pharmakokinetischen Eigenschaften unterscheiden .

Ähnliche Verbindungen:

  • Erythromycin
  • Clarithromycin
  • Roxithromycin

Die einzigartige Struktur und die Eigenschaften von this compound machen es zu einem wertvollen Antibiotikum mit breiten Anwendungen in der Medizin und Forschung.

Eigenschaften

Azithromycin usually is bacteriostatic, although the drug may be bactericidal in high concentrations against selected organisms. Bactericidal activity has been observed in vitro against Streptococcus pyogenes, S. pneumoniae, and Haemophilus influenzae. Azithromycin inhibits protein synthesis in susceptible organisms by penetrating the cell wall and binding to 50S ribosomal subunits, thereby inhibiting translocation of aminoacyl transfer-RNA and inhibiting polypeptide synthesis. The site of action of azithromycin appears to be the same as that of the macrolides (i.e., erythromycin, clarithromycin), clindamycin, lincomycin, and chloramphenicol. The antimicrobial activity of azithromycin is reduced at low pH. Azithromycin concentrates in phagocytes, including polymorphonuclear leukocytes, monocytes, macrophages, and fibroblasts. Penetration of the drug into phagocytic cells is necessary for activity against intracellular pathogens (e.g., Staphylococcus aureus, Legionella pneumophila, Chlamydia trachomatis, Salmonella typhi).

CAS-Nummer

83905-01-5

Molekularformel

C38H72N2O12

Molekulargewicht

749.0 g/mol

IUPAC-Name

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

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

InChI-Schlüssel

MQTOSJVFKKJCRP-FHZDSTMTSA-N

SMILES

CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O

Isomerische 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)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O

Kanonische SMILES

CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O

Aussehen

Solid powder

Color/Form

Amorphous solid

melting_point

113-115 °C
White crystalline powder. mp: 126 °C. Optical rotation: -41.4 deg at 26 °C/D (c = 1 in CHCl3) /Azithromycin dihydrate/

83905-01-5

Physikalische Beschreibung

Solid

Piktogramme

Irritant; Health Hazard; Environmental Hazard

Reinheit

>98% (or refer to the Certificate of Analysis)

Verwandte CAS-Nummern

117772-70-0 (dihydrate)
121470-24-4 (monohydrate)

Haltbarkeit

>2 years if stored properly

Löslichkeit

soluble in ethanol and DSMO, minimally soluble in water
5.14e-01 g/L

Lagerung

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Synonyme

Azadose
Azithromycin
Azithromycin Dihydrate
Azithromycin Monohydrate
Azitrocin
Azythromycin
CP 62993
CP-62993
CP62993
Dihydrate, Azithromycin
Goxal
Monohydrate, Azithromycin
Sumamed
Toraseptol
Ultreon
Vinzam
Zentavion
Zithromax
Zitromax

Dampfdruck

2.65X10-24 mm Hg at 25 °C (est)

Herkunft des Produkts

United States

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

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