Azithromycin

Modify Date: 2024-01-02 20:14:42

Azithromycin Structure
Azithromycin structure
 Common Name Azithromycin
CAS Number 83905-01-5 Molecular Weight 748.984
Density 1.2±0.1 g/cm3 Boiling Point 822.1±65.0 °C at 760 mmHg
Molecular Formula C38H72N2O12 Melting Point 113-115°C
MSDS Chinese USA Flash Point 451.0±34.3 °C
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Azithromycin


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

 Names

Name azithromycin
Synonym More Synonyms

 Azithromycin Biological Activity

Description Azithromycin is a macrolide antibiotic useful for the treatment of a number of bacterial infections.
Related Catalog
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.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 822.1±65.0 °C at 760 mmHg
Melting Point 113-115°C
Molecular Formula C38H72N2O12
Molecular Weight 748.984
Flash Point 451.0±34.3 °C
Exact Mass 748.508545
PSA 180.08000
LogP 3.33
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.537
Storage condition Store at -20°C
Stability Stable. Incompatible with strong oxidizing agents.

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H317-H334
Precautionary Statements P261-P280-P342 + P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi: Irritant;
Risk Phrases 42/43
Safety Phrases 22-36/37-45
RIDADR NONH for all modes of transport
RTECS RN6960000
HS Code 2941500000

 Synthetic Route

Formaldehyde structure

Formaldehyde

CAS#:50-00-0

Azathramycin structure

Azathramycin

CAS#:76801-85-9

~88%

Azithromycin Structure

Azithromycin

CAS#:83905-01-5

Literature: KOPRAN RESEARCH LABORATORIES LTD Patent: WO2007/15265 A2, 2007 ; Location in patent: Page/Page column 12-13 ;
structure

CAS#:1148112-33-7

~89%

Azithromycin Structure

Azithromycin

CAS#:83905-01-5

Literature: Kim, Hyoung Cheul; Kang, Sung Ho Angewandte Chemie - International Edition, 2009 , vol. 48, # 10 p. 1827 - 1829
Formaldehyde structure

Formaldehyde

CAS#:50-00-0

~%

Azithromycin Structure

Azithromycin

CAS#:83905-01-5

Literature: WO2007/80507 A2, ; Page/Page column 12 ;
Formaldehyde structure

Formaldehyde

CAS#:50-00-0

Formic Acid structure

Formic Acid

CAS#:64-18-6

Erythromycin A 9,11-Imino Ether structure

Erythromycin A ...

CAS#:161193-44-8

~%

Azithromycin Structure

Azithromycin

CAS#:83905-01-5

Literature: Tetrahedron, , vol. 53, # 50 p. 16923 - 16944

 Customs

HS Code 2941500000

 Articles141

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PLoS ONE 10 , e0132791, (2015)

Recently, extracts of Dalbergia trichocarpa bark have been shown to disrupt P. aeruginosa PAO1 quorum sensing (QS) mechanisms, which are key regulators of virulence factor expression and implicated in...

Macrolides rapidly inhibit red blood cell invasion by the human malaria parasite, Plasmodium falciparum.

BMC Biol. 13 , 52, (2015)

Malaria invasion of red blood cells involves multiple parasite-specific targets that are easily accessible to inhibitory compounds, making it an attractive target for antimalarial development. However...

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...

 Synonyms

(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)-b-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranoside
6-dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranoside
N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-on
Azithromycin
Ribotrex
(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)-b-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,
2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
MFCD00873574
Tobil
Zistic
Azithral
Arzomicin
Zithromac
(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
xz405
Aztrin
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
Setron
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)-
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(diméthylamino)-3-hydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-2-éthyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-méthoxy-4,6-diméthyltétrahydro-2H-pyran-2-yl]oxy}-3,5,6,8,10,12,14-heptaméthyl-1-oxa-6-azacyclopentadécan-15-one
Aruzilina
Zeto
1-oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-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-D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
Azadose
Aziwok
Azimin
Azenil
9-Deoxo-9a-methyl-9a-aza-9a-homoerythromycin A
azithromycinum [INN_la]
(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
XZ-450
Zifin
Ultreon
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)-
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