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Merck

1046067

USP

Azithromycin Identity

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Azithromycin

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About This Item

Empirical Formula (Hill Notation):
C38H72N2O12
CAS Number:
83905-01-5
Molecular Weight:
748.98
NACRES:
NA.24
PubChem Substance ID:
329749091
UNSPSC Code:
41116107
MDL number:
MFCD00873574

Product Name

Azithromycin Identity, United States Pharmacopeia (USP) Reference Standard

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

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 key

MQTOSJVFKKJCRP-BICOPXKESA-N

grade

pharmaceutical primary standard

API family

azithromycin

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

It was used as calibration standard at concentrations 3.90, 5.85, 7.80, 9.75 and 11.70 mg/mL during HPLC analysis to determine azithromycin in tablets and capsules.

General description

Azithromycin is a subclass of macrolides consisting of 15-membered macrocyclic lactone ring to which sugar moieties are linked.
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.

Other Notes

Sales restrictions may apply.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Aspects of degradation kinetics of azithromycin in aqueous solution.
Zhang, Yu, et al.
Chromatographia, 70.1-2, 67-73 (2009)
Development and validation of a micellar liquid chromatographic method with UV detection for determination of azithromycin in tablets and capsules.
Kulikov, A. U., and A. G. Verushkin.
Chromatographia, 60.1-2, 33-38 (2004)
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
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
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
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