117772-70-0 Usage
Uses
Used in Pharmaceutical Industry:
Azithromycin dihydrate is used as a broad-spectrum antibiotic for treating various infections, including respiratory, enteric, and genitourinary infections. It is effective against a wide range of pathogens and can be used as an alternative to other macrolides for some sexually transmitted and enteric infections.
Used in Respiratory Treatment:
Azithromycin dihydrate is used as a respiratory treatment due to its long half-life and high degree of tissue penetration, making it an effective choice for managing respiratory infections.
Used in Enteric and Genitourinary Infections:
Azithromycin dihydrate is used as an antibiotic for treating enteric and genitourinary infections, providing a broad-spectrum coverage against various pathogens.
Used in Cystic Fibrosis Treatment:
Azithromycin dihydrate is used as an anti-inflammatory and immunomodulatory agent in the treatment of cystic fibrosis, helping to manage inflammation and immune responses in the lungs.
Used in H1 Antihistamine Applications:
Azithromycin dihydrate is used as a non-sedating H1 antihistamine, providing relief from allergy symptoms without causing drowsiness.
Used in Antimicrobial Applications:
As an azalide antimicrobial agent, Azithromycin dihydrate is active in vitro against various pathogens, making it useful in treating a wide range of bacterial infections.
In vitro
Azithromycin displays a similar spectrum of antimicrobial activity. Azithromycin is marginally less active than erythromycin in vitro against Gram-positive organisms, although this is of doubtful clinical significance as susceptibility concentration fall within the range of achievable tissue Azithromycin concentrations. The mean MIC90 of Azithromycin against erythromycin susceptible/βL-ve strains, Streptococcus strains and NS (not selected for antimicrobial sesitivity)/erythromycin susceptible strains is 0.63, 0.35, and <0.27 mg/L, respectively. In contrast, Azithromycin appears to be more active than erythromycin against many Gram-negative pathogens and several other pathogens, notably Haemophilus influenza (MIC90, 1.34 mg/L), H. parainfluenzae(MIC90, 1 mg/L), Moraxella catarrhalis (MIC90, <0.1 mg/L), Neisseria gonorrhoeae (MIC90, 0.25 mg/L), Ureaplasma urealyticum, Bordetella spp (MIC90, 0.03-0.24 mg/L) and Borrelia burgdorferi. Azithromycin is also activity against clinical isolates of anaerobic bacteria Gram-positive cocci and propionibacterium acnes with MIC90 of 2.3, 0.03 mg/L. Like erythromycin and other macromycin, the activity of Azithromycin is unaffected by the production of β-lactamase. However, erythromycin-resistant organisms are also resistant to Azithromycin.
structure and hydrogen bonding
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 .
Mechanism of action
Azithromycin prevents bacteria from growing by interfering with their protein synthesis. It binds to the 50S subunit of the bacterial ribosome, thus inhibiting translation of mRNA. Nucleic acid synthesis is not affected.
Pharmacokinetics
Azithromycin is an acid-stable antibiotic, so it can be taken orally with no need of protection from gastric acids. It is readily absorbed, but absorption is greater on an empty stomach. Time to peak concentration (Tmax) in adults is 2.1 to 3.2 hours for oral dosage forms. Due to its high concentration in phagocytes, azithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations are released. The concentration of azithromycin in the tissues can be over 50 times higher than in plasma due to ion trapping and its high lipid solubility.[citation needed] Azithromycin's half-life allows a large single dose to be administered and yet maintain bacteriostatic levels in the infected tissue for several days. Following a single dose of 500 mg, the apparent terminal elimination half-life of azithromycin is 68 hours. Biliary excretion of azithromycin, predominantly unchanged, is a major route of elimination. Over the course of a week, about 6% of the administered dose appears as unchanged drug in urine.
Side Effects
Stomach upset, diarrhea/loose stools, nausea, vomiting, or abdominal pain may occur.
This medication may rarely cause a severe intestinal condition (Clostridium difficile-associated diarrhea) due to a resistant bacteria. This condition may occur during treatment or weeks to months after treatment has stopped.
Use of this medication for prolonged or repeated periods may result in oral thrush or a new yeast infection.
A very serious allergic reaction to this drug is rare. However, get medical help right away if you notice any symptoms of a serious allergic reaction, including: fever that doesn't go away, new or worsening lymph node swelling, rash, itching/swelling (especially of the face/tongue/throat), severe dizziness, trouble breathing.
Biochem/physiol Actions
Azithromycin dihydrate is a macrolide antibiotic, azalide subclass. It binds to the 50S subunit of the 70S bacterial ribosomes and inhibits RNA-dependent protein synthesis in bacterial cells. Azithromycin also has anti-immunomodulatory/anti-inflammatory properties, which make it useful in treating cystic fibrosis.
Check Digit Verification of cas no
The CAS Registry Mumber 117772-70-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,7,7 and 2 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 117772-70:
(8*1)+(7*1)+(6*7)+(5*7)+(4*7)+(3*2)+(2*7)+(1*0)=140
140 % 10 = 0
So 117772-70-0 is a valid CAS Registry Number.
117772-70-0Relevant academic research and scientific papers
A PROCESS FOR PREPARING 9-DEOXO-9A-AZA-9A-HOMOERYTHROMYCIN A
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Page/Page column 11, (2008/06/13)
The invention relates to a process for preparing 9-Deoxo-9a-aza-9a- homoerythromycin A of formula (III), which is an intermediate in the preparation of Azithromycin dihydrate.
Process of preparing a crystalline azithromycin monohydrate
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Page/Page column 5, (2008/06/13)
The present invention provides a process of preparing a crystalline azithromycin monohydrate. The process involves dissolving azithromycin in a solution containing ethanol, adding the dissolved azithromycin into water to precipitate the crystals, isolating and drying the precipitate to a water content of about 5% (w/w) to about 7% (w/w). The resulting azithromycin monohydrate is stable, exhibiting less than 2% degradation, and non-hydroscopic.
Stable non-dihydrate azithromycin oral suspensions
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Page/Page column 16, (2008/06/13)
This invention relates to a powder for oral suspension, and an oral suspension made there from, which comprises non-dihydrate azithromycin and an azithromycin conversion stabilizing excipient, wherein said excipient reduces the conversion of the form of azithromycin, when placed in suspension, to another form of azithromycin. This invention further relates to a method for reducing the conversion of a form of non-dihydrate azithromycin, in an oral suspension, by adding a surface tension reducing excipient that reduces the surface tension of the aqueous vehicle. Furthermore, this invention relates to a method for reducing the conversion of a non-dihydrate azithromycin, in an unflavored oral suspension, by raising the viscosity of the oral suspension, and in a flavored oral suspension by lowering the viscosity of the oral suspension.
PROCESS FOR PREPARING NON-HYGROSCOPIC AZITHROMYCIN DIHYDRATE
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Page 7, (2008/06/13)
A direct, single step process for preparing a semi-synthetic antibiotic azithromycin dihydrate (non-hygroscopic) is provided, by in situ reductive N-methylation of azaerythromycin A and subsequent crystallization from a mixture of acetone and water, preferably together with a catalytical quantity of a base such as liquor ammonia, which comprises: a) reacting azaerythromycin A with formic acid and formaldehyde in an organic solvent medium, to form a reaction mass comprising N-methylated azaerythromycin A (i.e. azithromycin); b) adding aqueous alkali solution to the reaction mass to form an aqueous phase and an organic phase; c) (i) when the organic solvent medium is acetone, separating the aqueous phase from the acetone organic phase, and removing the aqueous phase; or (ii) when the organic solvent medium is a solvent other than acetone, separating the aqueous phase from the organic phase and removing the aqueous phase, optionally washing the separated organic phase with aqueous alkali solution, completely distilling off the solvent from the organic phase to leave a residue, and adding acetone to dissolve the residue and form an acetone organic phase; d) adding water, and optionally a base, to the acetone organic phase to form a mixture, and allowing crystals to form in the mixture; e) recovering the crystals from the mixture and optionally washing the crystals; f) drying the crystals to obtain non-hygroscopic azithromycin dihydrate, and the yield of the non-hygroscopic azithromycin dihydrate of a pharmaceutically acceptable quality is obtained in yields up to 78-82% w/w.
Process for preparation of anhydrous azithromycin
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, (2008/06/13)
The present invention provides a stable form of azithromycin derivatives that act as antibiotics. These compounds are in anhydrous form and have increased stability over the hydrated forms.
Azithromycin preparation in its noncryst alline and crystalline dihydrate forms
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, (2008/06/13)
The present invention describes new procedures for the preparation of the macrolide azithromycin in its non-crystalline and crystalline dihydrate forms, which are characterized and clearly differentiated by means of the following methods and techniques: 1. IR Spectroscopy. 2. Differential Scan Calorimetry (DSC). 3. X-Ray Diffraction. 4. Hygroscopicity. 5. Crystallinity test (Light Polarized Microscopy)
Azithromycin dihydrate
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, (2008/06/13)
Non-hygroscopic, azithromycin (9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin) dihydrate and a process therefor.
Preparation of azithromycin dihydrate
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, (2008/06/13)
Azithromycin dihydrate is prepared from azithromycin by adding a base to an aqueous solution of azithromycin to crystallise the dihydrate, the aqueous solution having a pH of from 1 to 5 and containing acetone.
Azithromycin and derivatives as antiprotozoal agents
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, (2008/06/13)
A method of use of azithromycin or derivatives of azithromycin in the treatment of infection caused by Toxoplasma gondii in mammals is disclosed.
