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75199

Sigma-Aldrich

Azithromycin

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

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

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H317,H334,H410

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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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
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
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
Alison M Binder et al.
American journal of respiratory and critical care medicine, 188(7), 807-812 (2013-08-10)
Persons with cystic fibrosis (CF) are at high risk of nontuberculous mycobacterial (NTM) infection, with treatment requiring prolonged multidrug regimens that include macrolides. Although macrolides, specifically azithromycin, are used in the management of patients with CF with chronic Pseudomonas, macrolide-resistant
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
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