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Merck
CN

1134390

USP

Clarithromycin Identity

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Clarithromycin

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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:
329749413
UNSPSC Code:
41116107
MDL number:
MFCD00865140

Key Documents

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Product Name

Clarithromycin Identity, United States Pharmacopeia (USP) Reference Standard

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

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 key

AGOYDEPGAOXOCK-KCBOHYOISA-N

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 Identity 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
  • Clarithromycin Tablets
  • Clarithromycin Extended-Release 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.

Regulatory Information

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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
Stig Lyngbæk et al.
European journal of preventive cardiology, 21(10), 1275-1284 (2013-06-01)
Low prevalence of detectable cardiac troponin in healthy people and low-risk patients previously curtailed its use. With a new high-sensitive cardiac troponin assay (hs-cTnT), concentrations below conventional detection may have prognostic value, notably in combination with N-terminal pro-B-type natriuretic peptide
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
Jerry M Zuckerman et al.
Infectious disease clinics of North America, 23(4), 997-1026 (2009-11-17)
The advanced macrolides, azithromycin and clarithromycin, and the ketolide, telithromycin, are structural analogs 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. Clarithromycin
Evangelos J Giamarellos-Bourboulis
Current topics in medicinal chemistry, 10(14), 1470-1475 (2010-06-12)
Macrolides currently play a major role in the management of severe infections. Evidence derives from several retrospective studies have shown a significant reduction of mortality from community-acquired pneumonia upon treatment with a macrolide. Apart from other explanations, their effect is
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