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Merck

1134379

USP

Clarithromycin

United States Pharmacopeia (USP) Reference Standard

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About This Item

Empirical Formula (Hill Notation):
C38H69NO13
CAS Number:
81103-11-9
Molecular Weight:
747.95
NACRES:
NA.24
PubChem Substance ID:
329749411
UNSPSC Code:
41116107
MDL number:
MFCD00865140

Key Documents

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Product Name

Clarithromycin, United States Pharmacopeia (USP) Reference Standard

InChI key

AGOYDEPGAOXOCK-KCBOHYOISA-N

SMILES string

O[C@@H]([C@@](O)(C)[C@@H](CC)OC([C@H](C)[C@H]1O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(OC)C2)=O)[C@@H](C)C([C@H](C)C[C@@](C)(OC)[C@H](O[C@@H]3O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@H]1C)=O

InChI

1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

grade

pharmaceutical primary standard

API family

clarithromycin

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

Clarithromycin USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Clarithromycin Extended-Release Tablets
  • Clarithromycin for Oral Suspension
  • Clarithromycin Tablets

Biochem/physiol Actions

Clarithromycin is a macrolide antibiotic that interferes with bacterial protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against Gram-negative bacteria. It has a short half-life, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.

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.

Other Notes

Sales restrictions may apply.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Keith A Rodvold et al.
Antimicrobial agents and chemotherapy, 47(8), 2450-2457 (2003-07-25)
The purpose of this study was to compare the concentrations of levofloxacin and azithromycin in steady-state plasma, epithelial lining fluid (ELF), and alveolar macrophage (AM) after intravenous administration. Thirty-six healthy, nonsmoking adult subjects were randomized to either intravenous levofloxacin (500
Chung-Su Park et al.
The American journal of gastroenterology, 109(10), 1595-1602 (2014-08-06)
Helicobacter pylori eradication rates with clarithromycin-based triple therapy are declining, and an alternative strategy is needed urgently. We sought to compare the efficacy of pretreatment antimicrobial susceptibility-guided vs. clarithromycin-based triple therapy for H. pylori eradication in a region with high
Alicia C Marin et al.
Expert opinion on pharmacotherapy, 14(7), 843-861 (2013-03-30)
Helicobacter pylori infection is generally treated with therapies that include a proton pump inhibitor (PPI) and, at least, two antibiotics being clarithromycin one of the most used. Antibiotic resistance, mainly to clarithromycin, seems to be increasing in many geographical areas
Jerry M Zuckerman
Infectious disease clinics of North America, 18(3), 621-649 (2004-08-17)
The advanced macrolides, azithromycin and clarithromycin, and the ketolide telithromycin are structural analogues of erythromycin. They have several distinct advantages when compared with erythromycin including enhanced spectrum of activity, more favorable pharmacokinetics and pharmacodynamics, once daily administration, and improved tolerability.
Li Jing Xiong et al.
Helicobacter, 18(2), 89-101 (2012-10-17)
Helicobacter pylori infection is acquired mainly during childhood. To eradicate H. pylori, clarithromycin-based triple therapy has been recommended in children and adults by the latest Maastricht Consensus. However, the prevalence of clarithromycin-resistant H. pylori was higher in children than that
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