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Y0000306

Azithromycin

European Pharmacopoeia (EP) Reference Standard

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Synonym(s):
Azithromycin dihydrate, N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A, CP-62993
Empirical Formula (Hill Notation):
C38H72N2O12 · 2H2O
CAS Number:
Molecular Weight:
785.02
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

azithromycin

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

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

InChI key

SRMPHJKQVUDLQE-KUJJYQHYSA-N

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1 of 4

This Item
PHR1088Y00006371046056
vibrant-m

Y0000306

Azithromycin

vibrant-m

PHR1088

Azithromycin

vibrant-m

1046056

Azithromycin

grade

pharmaceutical primary standard

grade

certified reference material, pharmaceutical secondary standard

grade

pharmaceutical primary standard

grade

pharmaceutical primary standard

manufacturer/tradename

EDQM

manufacturer/tradename

-

manufacturer/tradename

EDQM

manufacturer/tradename

USP

format

neat

format

neat

format

neat

format

neat

API family

azithromycin

API family

azithromycin

API family

azithromycin

API family

-

storage temp.

2-8°C

storage temp.

-10 to -25°C

storage temp.

2-8°C

storage temp.

-

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Azithromycin EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

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.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Related product

Product No.
Description
Pricing

pictograms

Health hazardEnvironment

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
Eric M Mortensen et al.
JAMA, 311(21), 2199-2208 (2014-06-04)
Although clinical practice guidelines recommend combination therapy with macrolides, including azithromycin, as first-line therapy for patients hospitalized with pneumonia, recent research suggests that azithromycin may be associated with increased cardiovascular events. To examine the association of azithromycin use with all-cause
Sheila K West et al.
The Journal of infectious diseases, 210(1), 65-71 (2014-01-22)
Trachoma, caused by repeated infections with ocular Chlamydia trachomatis, is targeted for elimination using multiple annual rounds of mass drug administration (MDA) in endemic communities. Infection rates do not decline as expected in some communities, leading to concerns about azithromycin
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
Sarah E Burr et al.
Bulletin of the World Health Organization, 92(7), 490-498 (2014-08-12)
To evaluate the effect of repeated mass drug administration (MDA) of azithromycin in the Gambia on the nasopharyngeal carriage of Streptococcus pneumoniae and on the emergence of antibiotic-resistant strains. This study involved villages that participated in a cluster randomized trial

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