Azithromycin Dihydrate

Names

[ Name ]:
Azithromycin Dihydrate

[Synonym ]:
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-Ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside dihydrate
1-Oxa-6-azacyclopentadecan-15-one
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)-b η-D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-, hydrate (1:2)
N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A CP-62993
Azithromycindihydrate
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,3S,4R,5R,8R,10R,11R,12S,13S,14R)-, hydrate (1:2)
Azithromycin Dihydrate
Azithromycin (hydrate)

Biological Activity

[Description]:

Azithromycin hydrate is a macrolide antibiotic useful for the treatment of a number of bacterial infections.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[In Vitro]

Azithromycin (2 μM) augments rhinovirus-induced IFNβ expression in primary bronchial epithelial cells from asthmatics, which is associated with over-expression of RIG-I like receptors and repression of viral replication. Knockdown of MDA5, but not knockdown of RIG-I, diminishes azithromycin (2 μM)-enhanced viral-induced IFNβ expression in asthmatic primary bronchial epithelial cells[1]. Azithromycin specifically reduces MMP-9 mRNA and protein levels without affecting NF-κB in endotoxin-challenged monocytic THP-1 cells[2].

[In Vivo]

Azithromycin (50 mg/kg) has no effect on bronchoalveolar lavage inflammatory parameters and LDH levels in a mouse model of asthma exacerbation. Azithromycin induces neither general inflammatory parameters nor LDH release in a mouse model of asthma exacerbation, and augments expression of interferon-stimulated genes and the pattern recognition receptor MDA5 but not RIG-I in exacerbating mice[1].

[Cell Assay]

THP-1 cells (106 cells in 1 mL RPMI medium, without antibiotics, growth factors or serum) are seeded in each well of 24-well plates and allowed to settle for 1 hour. Next, 50 μL of the test compound is added followed by 50 μL of LPS (final concentration of 10 μg/mL). After 24h (37°C and 5% CO2) the supernatants and cell pellets are collected (1200 rpm, 5 min). THP-1 cell viability is tested using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). MTT is dissolved at 2 mg/mL in PBS and aliquots are stored at -20°C. The MTT assay is performed according to the suppliers instructions. Absorbance of MTT converted into formazan is measured at a wavelength of 570 nm with background subtraction at 630 nm.

[References]

[1]. Menzel M, et al. Azithromycin augments rhinovirus-induced IFNβ via cytosolic MDA5 in experimental models of asthma exacerbation. Oncotarget. 2017 Mar 18.

[2]. Vandooren J, et al. Differential inhibition of activity, activation and gene expression of MMP-9 in THP-1 cells by azithromycin and minocycline versus bortezomib: A comparative study. PLoS One. 2017 Apr 3;12(4):e0174853.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.18g/cm3

[ Boiling Point ]:
822.1ºC at 760mmHg

[ Melting Point ]:
113-115ºC

[ Molecular Formula ]:
C₃₈H₇₆N₂O₁₄

[ Molecular Weight ]:
785.015

[ Flash Point ]:
451ºC

[ Exact Mass ]:
784.529663

[ PSA ]:
198.54000

[ LogP ]:
1.71000

[ Vapour Pressure ]:
2.51E-31mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
24/25-36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RN6960000

[ HS Code ]:
29419000

Articles

Environmental friendly method for urban wastewater monitoring of micropollutants defined in the Directive 2013/39/EU and Decision 2015/495/EU.

J. Chromatogr. A. 1418 , 140-9, (2015)

The fate and removal of organic micropollutants in the environment is a demanding issue evidenced by the recent European policy. This work presents an analytical method for the trace quantification of...

Purification and characterization of the Staphylococcus aureus bacillithiol transferase BstA.

Biochim. Biophys. Acta 1840(9) , 2851-61, (2014)

Gram-positive bacteria in the phylum Firmicutes synthesize the low molecular weight thiol bacillithiol rather than glutathione or mycothiol. The bacillithiol transferase YfiT from Bacillus subtilis wa...

A comparison of in vitro ADME properties and pharmacokinetics of azithromycin and selected 15-membered ring macrolides in rodents.

Eur. J. Drug Metab. Pharmacokinet. 39(4) , 263-76, (2014)

The purpose of this study was to evaluate the impact of structural modifications on the 15-membered macrolactone ring and/or substituents on the in vitro ADME properties and in vivo pharmacokinetic (P...