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Azithromycin

Name: Azithromycin
Brand: SIGMA

Synonym(s):

CP 62,993

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About This Item

Empirical Formula (Hill Notation):

C₃₈H₇₂N₂O₁₂

CAS Number:

83905-01-5

Molecular Weight:

748.98

MDL number:

MFCD00873574

UNSPSC Code:

12352200

PubChem Substance ID:

329766256

NACRES:

NA.77

form

powder

Quality Level

200

optical activity

[α]/D −45±2°, c = 1% in ethanol

antibiotic activity spectrum

viruses

application(s)

environmental

Mode of action

protein synthesis | interferes

SMILES string

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O

InChI

1S/C38H72N2O12/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/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

InChI key

MQTOSJVFKKJCRP-BICOPXKESA-N

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General description

Azithromycin is a hydrophobic azalide and a derivative of erythromycin. It belongs to the macrolide class of antibodies.

Application

Azithromycin has been used:

to treat synchronized Plasmodium falciparum Dd2 parasites for continuous growth assays to study the antiparasitic mechanisms of doxycycline (DOX)
to study its bactericidal activity against Pseudomonas aeruginosa in combination with a recombinant hemolymph plasma lectin (rHPLOE)
in evolution experiments to study P. aeruginosa strain PA14’s response to bacteriostatic antibiotics

Biochem/physiol Actions

Azithromycin is a broad-spectrum antimicrobial agent, effective against infections associated with respiratory tract, skin, tissues, and genital chlamydia. It acts against Gram-negative bacteria (including Enterobacteriaceae) and several Gram-positive organisms. It also acts against Plasmodium falciparum and P. vivax, which are multidrug resistance species that transmit malaria. Azithromycin targets the plasmodial ribosome and prevents protein synthesis. It is soluble in lipids and metabolizes in the liver by undergoing demethylation. It is commonly used to treat community-acquired pneumonia, sexually transmitted diseases, acute otitis media, and acute exacerbation of chronic obstructive pulmonary disease (COPD).

Features and Benefits

Rapidly absorbed
Shows great tissue penetration and procures high intracellular concentration
Distributes widely in body fluids and tissues

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

GHS08,GHS09

Signal Word

Danger

Hazard Statements

H317 - H334 - H410

Precautionary Statements

P261 - P272 - P273 - P280 - P284 - P302 + P352

Hazard Classifications

Aquatic Chronic 1 - Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Early Administration of Azithromycin and Prevention of Severe Lower Respiratory Tract Illnesses in Preschool Children With a History of Such Illnesses: A Randomized Clinical Trial.

Leonard B Bacharier et al.

JAMA, 314(19), 2034-2044 (2015-11-18)

Many preschool children develop recurrent, severe episodes of lower respiratory tract illness (LRTI). Although viral infections are often present, bacteria may also contribute to illness pathogenesis. Strategies that effectively attenuate such episodes are needed. To evaluate if early administration of

Novel high-throughput screening method using quantitative PCR to determine the antimicrobial susceptibility of Orientia tsutsugamushi clinical isolates.

Weerawat Phuklia et al.

The Journal of antimicrobial chemotherapy, 74(1), 74-81 (2018-10-09)

To develop a method to enable the large-scale antimicrobial susceptibility screening of Orientia tsutsugamushi clinical isolates, using one timepoint and one concentration of antibiotics to considerably speed up the time to result. Growth, harvesting, multiplicity of infection (moi) and the

Haemophilus influenzae responds to glucocorticoids used in asthma therapy by modulation of biofilm formation and antibiotic resistance.

Chris S Earl et al.

EMBO molecular medicine, 7(8), 1018-1033 (2015-05-23)

Glucocorticosteroids are used as a main treatment to reduce airway inflammation in people with asthma who suffer from neutrophilic airway inflammation, a condition frequently associated with Haemophilus influenzae colonization. Here we show that glucocorticosteroids have a direct influence on the

Zika virus cell tropism in the developing human brain and inhibition by azithromycin.

Hanna Retallack et al.

Proceedings of the National Academy of Sciences of the United States of America, 113(50), 14408-14413 (2016-12-03)

The rapid spread of Zika virus (ZIKV) and its association with abnormal brain development constitute a global health emergency. Congenital ZIKV infection produces a range of mild to severe pathologies, including microcephaly. To understand the pathophysiology of ZIKV infection, we

An international ISHLT/ATS/ERS clinical practice guideline: diagnosis and management of bronchiolitis obliterans syndrome.

Keith C Meyer et al.

The European respiratory journal, 44(6), 1479-1503 (2014-11-02)

Bronchiolitis obliterans syndrome (BOS) is a major complication of lung transplantation that is associated with poor survival. The International Society for Heart and Lung Transplantation, American Thoracic Society, and European Respiratory Society convened a committee of international experts to describe

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