Azathramycin

Names

[ Name ]:
Azathramycin

[Synonym ]:
9-deokso-9a-aza-9a-homoeritromicin A
Desmethylazithromycin
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-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
9a-N-desmethyl azithromycin
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-Ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-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
DD-Azaerythromycin A
10-Dihydro-10-deoxo-11-azaerythromycin A
9-Deoxo-9a-aza-9a-homo Erythromycin A(Desmethyl Azithromycin)
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-Ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-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
9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A
9a-aza-9-deoxo-9a-homoerythromycin A
9-deoxo-9a-aza-9a-homoerythromycin
Azaerythromycin A
UNII-4LSP9FJT5B
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-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β -D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
9-deoxo-9a-aza-9a-homoerythromycin A
Azathramycin

Biological Activity

[Description]:

Azathramycin is an antibiotic.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Noedl H, Krudsood S, Leowattana W, In vitro antimalarial activity of azithromycin, artesunate, and quinine in combination and correlation with clinical outcome. Antimicrob Agents Chemother. 2007 Feb;51(2):651-6.

[2]. Hiwatashi Y, Maeda M, Fukushima H, Azithromycin suppresses proliferation, interleukin production and mitogen-activated protein kinases in human peripheral-blood mononuclear cells stimulated with bacterial superantigen. J Pharm Pharmacol. 2011 Oct;63(10):1320-6.

[3]. Fernandez-Obregon AC. Azithromycin for the treatment of acne. Int J Dermatol. 2000 Jan;39(1):45-50.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
815.2±65.0 °C at 760 mmHg

[ Melting Point ]:
126-136ºC

[ Molecular Formula ]:
C₃₇H₇₀N₂O₁₂

[ Molecular Weight ]:
734.958

[ Flash Point ]:
446.8±34.3 °C

[ Exact Mass ]:
734.492859

[ PSA ]:
188.87000

[ LogP ]:
3.11

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
-20℃

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Peptide-mediated macrolide resistance reveals possible specific interactions in the nascent peptide exit tunnel.

Mol. Microbiol. 54(2) , 376-85, (2004)

Expression of specific short peptides can render cells resistant to macrolide antibiotics. Peptides conferring resistance to structurally different macrolides including oleandomycin, azithromycin, aza...

Quantitative thin-layer chromatographic method of analysis of azithromycin in pure and capsule forms.

J. Chromatogr. Sci. 41(1) , 10-6, (2003)

A validated stability-indicating thin-layer chromatographic (TLC) method of the analysis of azithromycin (AZT) in bulk and capsule forms is developed. Both AZT potential impurity and degradation produ...

Erythromycin series. XII. Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A: synthesis and structure-activity relationship of its acyl derivatives.

J. Antibiot. 40(7) , 1006-15, (1987)

Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A (5), the new 15-membered semi-synthetic macrolide antibiotic with nitrogen as additional atom in the aglycone ring of eryt...