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75199

Sigma-Aldrich

Azithromycin

Synonyme(s) :

CP 62,993

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About This Item

Formule empirique (notation de Hill):
C38H72N2O12
Numéro CAS:
83905-01-5
Poids moléculaire :
748.98
Numéro MDL:
MFCD00873574
Code UNSPSC :
12352200
ID de substance PubChem :
329766256
Nomenclature NACRES :
NA.77

Forme

powder

Activité optique

[α]/D −45±2°, c = 1% in ethanol

Spectre d'activité de l'antibiotique

viruses

Application(s)

environmental

Mode d’action

protein synthesis | interferes

Chaîne SMILES 

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

Clé InChI

MQTOSJVFKKJCRP-BICOPXKESA-N

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Description générale

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

Actions biochimiques/physiologiques

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).

Caractéristiques et avantages

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

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Health hazardEnvironment
GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H317,H334,H410

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
Katharina Krenn et al.
The Journal of thoracic and cardiovascular surgery, 149(4), 1194-1202 (2015-01-18)
Azithromycin has become a standard of care in therapy of bronchiolitis obliterans following lung transplantation. Matrix metalloprotease-9 broncho-alveolar lavage levels increase in airway neutrophilia and bronchiolitis obliterans. Interleukin-17 may play a role in lung allograft rejection, and interleukin-12 is downregulated
Patricia C Valery et al.
The Lancet. Respiratory medicine, 1(8), 610-620 (2014-01-28)
Indigenous children in high-income countries have a heavy burden of bronchiectasis unrelated to cystic fibrosis. We aimed to establish whether long-term azithromycin reduced pulmonary exacerbations in Indigenous children with non-cystic-fibrosis bronchiectasis or chronic suppurative lung disease. Between Nov 12, 2008
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