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Key Documents

PZ0007

Sigma-Aldrich

Azithromycin dihydrate

≥98% (HPLC), powder, 50S ribosomal subunit formation and elongation inhibitor

Synonyme(s) :

1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-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)-beta-D-xylohexopyranosyl]oxy]-, dihydrate, [2R-(2R, 3S, 4R, 5R, 8R, 10R, 11R, 12S, 13S, 14R)]-, N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A, CP-62993

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About This Item

Formule empirique (notation de Hill):
C38H72N2O12 · 2H2O
Numéro CAS:
Poids moléculaire :
785.02
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Azithromycin dihydrate, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

off-white

Solubilité

DMSO: >20 mg/mL

Température de stockage

room temp

Chaîne SMILES 

O.O.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/C38H72N2O12.2H2O/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;2*1H2/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-;;/m1../s1

Clé InChI

SRMPHJKQVUDLQE-KUJJYQHYSA-N

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Application

Azithromycin dihydrate has been used:
  • in blocking buffer (5% bovine serum albumin) for indirect immunofluorescence
  • in treating the U87 cells for cell-viability assay and flow cytometry analysis to study the Zika virus infection in glial cells
  • in antibiotic co-treatment experiments, to compare its antibacterial activity with PYRRO-C3D against Streptococcus pneumoniae biofilms

Actions biochimiques/physiologiques

Azithromycin dihydrate is a macrolide antibiotic, azalide subclass. It binds to the 50S subunit of the 70S bacterial ribosomes and inhibits RNA-dependent protein synthesis in bacterial cells. Azithromycin also has anti-immunomodulatory/anti-inflammatory properties, which make it useful in treating cystic fibrosis.
Azithromycin is a non-β-lactam antibody, effective against infections associated with respiratory tract, skin, tissues and genital chlamydia. It also acts against Plasmodium falciparum and P. vivax, which are multidrug resistance species that transmit malaria. Azithromycin targets the ribosome and prevents protein synthesis. It is soluble in lipids and metabolizes in liver by undergoing demethylation.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Travelers' Malaria, 131-131 (2008)
Paul N Newton et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 68(5), 738-747 (2018-07-19)
Murine typhus, or infection with Rickettsia typhi, is a global but neglected disease without randomized clinical trials to guide antibiotic therapy. A prospective, open, randomized trial was conducted in nonpregnant, consenting inpatient adults with rapid diagnostic test evidence of uncomplicated
Human Sertoli cells support high levels of Zika virus replication and persistence
Kumar A, et al.
Scientific Reports, 8(1), 5477-5477 (2018)
Cephalosporin-NO-donor prodrug PYRRO-C3D shows beta-lactam-mediated activity against Streptococcus pneumoniae biofilms
Allan RN, et al.
Nitric Oxide, 65, 43-49 (2017)
Alexander J Currie et al.
Frontiers in cellular and infection microbiology, 10, 372-372 (2020-08-15)
Excessive inflammation by phagocytes during Aspergillus fumigatus infection is thought to promote lung function decline in CF patients. CFTR modulators have been shown to reduce A. fumigatus colonization in vivo, however, their antifungal and anti-inflammatory mechanisms are unclear. Other treatments

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