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83905-01-5

83905-01-5 structure
83905-01-5 structure
  • Name: Azithromycin
  • Chemical Name: azithromycin
  • CAS Number: 83905-01-5
  • Molecular Formula: C38H72N2O12
  • Molecular Weight: 748.984
  • Catalog: API Antibiotics Macrolide drug
  • Create Date: 2018-02-08 08:00:00
  • Modify Date: 2025-08-21 10:54:50
  • Azithromycin is a macrolide antibiotic useful for the treatment of a number of bacterial infections.
Name azithromycin
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)-
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.
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.
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
50-00-0 structure

50-00-0

76801-85-9 structure

76801-85-9

~88%

83905-01-5 structure

83905-01-5

Literature: KOPRAN RESEARCH LABORATORIES LTD Patent: WO2007/15265 A2, 2007 ; Location in patent: Page/Page column 12-13 ;
1148112-33-7 structure

1148112-33-7

~89%

83905-01-5 structure

83905-01-5

Literature: Kim, Hyoung Cheul; Kang, Sung Ho Angewandte Chemie - International Edition, 2009 , vol. 48, # 10 p. 1827 - 1829
50-00-0 structure

50-00-0

~%

83905-01-5 structure

83905-01-5

Literature: WO2007/80507 A2, ; Page/Page column 12 ;
50-00-0 structure

50-00-0

64-18-6 structure

64-18-6

161193-44-8 structure

161193-44-8

~%

83905-01-5 structure

83905-01-5

Literature: Tetrahedron, , vol. 53, # 50 p. 16923 - 16944
HS Code 2941500000
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