CAS 83905-01-5|Azithromycin

Introduction：Basic information about CAS 83905-01-5|Azithromycin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Azithromycin BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Articles141
7. Synonyms

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	ChineseUSA	Flash Point	451.0±34.3 °C
Symbol	GHS08	Signal Word	Danger

Names

Name	azithromycin
Synonym	More Synonyms

Azithromycin BiologicalActivity

Description	Azithromycin is a macrolide antibiotic useful for the treatment of a number of bacterial infections.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Anti-infection >>BacterialResearch 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.

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
InChIKey	MQTOSJVFKKJCRP-ZOFOWXHFSA-N
SMILES	CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC2OC(C)CC(N(C)C)C2O)C(C)(O)CC(C)CN(C)C(C)C(O)C1(C)O
Storage condition	Store at -20°C
Stability	Stable. Incompatible with strong oxidizing agents.

Safety Information

Symbol	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

Customs

HS Code	2941500000

Articles141

Pseudomonas aeruginosa Biofilm Formation and Persistence, along with the Production of Quorum Sensing-Dependent Virulence Factors, Are Disrupted by a Triterpenoid Coumarate Ester Isolated from Dalbergia trichocarpa, a Tropical Legume.

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

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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