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Azithromycin Dihydrate

CAS# 117772-70-0

Azithromycin Dihydrate

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Chemical structure

Azithromycin Dihydrate

3D structure

Chemical Properties of Azithromycin Dihydrate

Cas No. 117772-70-0 SDF Download SDF
PubChem ID 3033819 Appearance Powder
Formula C38H76N2O14 M.Wt 785.02
Type of Compound N/A Storage Desiccate at -20°C
Synonyms CP-62993 dihydrate
Solubility Soluble to 100 mg/mL (127.38 mM) in DMSO
Chemical Name (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one;dihydrate
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.O.O
Standard InChIKey SRMPHJKQVUDLQE-KUJJYQHYSA-N
Standard InChI InChI=1S/C38H72N2O12.2H2O/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;2*1H2/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-;;/m1../s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Azithromycin Dihydrate

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

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.

Protocol

Cell Assay [2]
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.

Azithromycin Dihydrate Dilution Calculator

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Azithromycin Dihydrate Molarity Calculator

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Preparing Stock Solutions of Azithromycin Dihydrate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2739 mL 6.3693 mL 12.7385 mL 25.4771 mL 31.8463 mL
5 mM 0.2548 mL 1.2739 mL 2.5477 mL 5.0954 mL 6.3693 mL
10 mM 0.1274 mL 0.6369 mL 1.2739 mL 2.5477 mL 3.1846 mL
50 mM 0.0255 mL 0.1274 mL 0.2548 mL 0.5095 mL 0.6369 mL
100 mM 0.0127 mL 0.0637 mL 0.1274 mL 0.2548 mL 0.3185 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Azithromycin Dihydrate

Azithromycin Dihydrate is an acid stable orally administered macrolide antimicrobial drug, structurally related to erythromycin.

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References on Azithromycin Dihydrate

Development, characterization and solubility study of solid dispersions of azithromycin dihydrate by solvent evaporation method.[Pubmed:22247849]

J Adv Pharm Technol Res. 2010 Apr;1(2):221-8.

Azithromycin Dihydrate (Poorly water soluble drug), when prepared as solid dispersion showed improved solubility and dissolution. So the main purpose of this investigation was to increase the solubility and dissolution rate of Azithromycin Dihydrate by the preparation of its solid dispersion with urea using solvent evaporation method. Physical mixtures and solid dispersions of Azithromycin Dihydrate were prepared by using urea as water-soluble carrier in various proportions (1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7 by weight), by employing solvent evaporation method. The drug release profile was studied and it was found that the dissolution rate and the dissolution parameters of the drug from the physical mixture as well as solid dispersion were higher than those of the intact drug. FT- IR spectra revealed no chemical incompatibility between drug and urea. Drug-polymer interactions were investigated using differential scanning calorimetry (DSC) and Powder X-Ray Diffraction (PXRD).

Efficacy of azithromycin dihydrate in treatment of cryptosporidiosis in naturally infected dairy calves.[Pubmed:16095179]

J Vet Intern Med. 2005 Jul-Aug;19(4):590-3.

The objective of this study was to evaluate the therapeutic efficacy of azithromycin treatment of cryptosporidiosis in naturally infected calves under field conditions. Fifty Holstein calves with cryptosporidiosis infection were divided into 5 groups: 1 group (10 calves) was unmedicated and served as the control group and was given distilled water only, whereas the other groups (10 animals per group) were medicated orally with azithromycin at the doses of 500 (group 1), 1,000 (group 2), 1,500 (group 3), and 2,000 mg (group 4) PO once daily for 7 days. The animals were examined clinically and fecal samples were collected on the 1st (inclusion day), 7th, 14th, and 21st days of the study. Drug efficacy was assessed by evaluating diarrhea, oocyst shedding, and weight gains from days 1 to 21 (4 assessments). Significant differences were observed in reductions of oocyst shedding (P < .05) and the fecal diarrhea incidence (P < .05) in groups 3 and 4 when compared with groups 1 and 2 and the control group. Weight gain of medicated calves was significantly higher than that of the unmedicated calves throughout the study (P < .05). The drug significantly suppressed oocyst shedding and resulted in significant improvements in clinical signs. Therefore, this suppression may have significant effect on the reduction of environmental contamination by cryptosporidial oocysts. From the economic point view, authors suggest that the most effective dose of azithromycin for the treatment of cryptosporidiosis in calves should be at 1,500 mg/d for 7 days.

Description

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

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