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Merck

1046056

USP

Azithromycin

United States Pharmacopeia (USP) Reference Standard

Sinónimos:

Azithromycin dihydrate, 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]-, [2R-(2R, 3S, 4R, 5R, 8R, 10R, 11R, 12S, 13S, 14R)]- dihydrate, N-Methyl-11-aza-10-deoxo-10-dihydroerythromycin A, CP-62993

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Fórmula empírica (notación de Hill):
C38H72N2O12 · 2H2O
Número CAS:
117772-70-0
Peso molecular:
785.02
NACRES:
NA.24
PubChem Substance ID:
329749090
UNSPSC Code:
41116107
MDL number:
MFCD01862248

Documentos clave

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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

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 key

SRMPHJKQVUDLQE-KUJJYQHYSA-N

grade

pharmaceutical primary standard

agency

USP

API family

azithromycin

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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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.

Application

Azithromycin USP reference standard for use in specified quality tests and assays.

Also used to prepare standard, standard stock solutions for the assay, identification, performance, and impurity analysis according to the given below monographs of United States Pharmacopeia (USP):
  • Azithromycin for Oral Suspension
  • Azithromycin Capsules
  • Azithromycin for Injection

Biochem/physiol Actions

Azithromycin dihydrate is a macrolide antibiotic with anti-immunomodulatory/anti-inflammatory properties.
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.

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.  ​

Other Notes

Sales restrictions may apply.
USP issued SDS can be found here

Clase de almacenamiento

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number

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Azithromycin for Injection
United States Pharmacopeia, 44(2), 451-451 (2020)
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)
Aspects of degradation kinetics of azithromycin in aqueous solution.
Zhang, Yu, et al.
Chromatographia, 70.1-2, 67-73 (2009)
R Hirsch et al.
Journal of periodontal research, 47(2), 137-148 (2011-11-05)
Azithromycin is a macrolide antibiotic used extensively in medicine for the treatment of a wide range of infections such as upper respiratory tract infections, middle ear infections, sexually transmitted infections and trachoma. It is also effective against the most common
Erik B Wilms et al.
Pediatric pulmonology, 47(7), 658-665 (2012-06-12)
Azithromycin maintenance therapy results in improvement of respiratory function in patients with cystic fibrosis (CF). In azithromycin maintenance therapy, several dosing schemes are applied. In this review, we combine current knowledge about azithromycin pharmacokinetics with the dosing schedules used in
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