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Merck

C9742

Clarithromycin

≥95% (HPLC)

Synonym(s):

6-O-methyl erythromycin

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About This Item

Empirical Formula (Hill Notation):
C38H69NO13
CAS Number:
81103-11-9
Molecular Weight:
747.95
NACRES:
NA.76
PubChem Substance ID:
329775082
UNSPSC Code:
51102829
MDL number:
MFCD00865140

Product Name

Clarithromycin, ≥95% (HPLC)

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

assay

≥95% (HPLC)

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

Quality Level

200

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Application

Clarithromycin is a semisynthetic macrolide antibiotic that is derived from erythromycin. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration . Clarithromycin may be used to attenuate cardiac transplantation rejection via matrix metalloproteinase suppression. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD). It is used to study bacterial protein synthesis and peptide translation.

Biochem/physiol Actions

Clarithromycin inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation. Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Clarithromycin penetrates the bacteria cell wall and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome, blocking translocation of aminoacyl transfer-RNA and polypeptide synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
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

Chemical structure: macrolide

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Preparation Note

Practically insoluble in water, soluble in acetone and methylene chloride, slightly soluble in methanol.

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000478498
0000478498
0000478499
0000478499
0000426430

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. I want to use Carithromycin, Product C9742, in cell culture.  What solvent can I use?

    One reference mentions making stock solutions in ethanol at 2 mg/mL (Kikuchi, T., et al., J. Antimicrobial Chemotherapy, 49, 745-755 (2002)). Another paper infers that clarithromycin is soluble in ethanol to a minimum of 30 mg/mL. (Hoffman, H.L. et al., Antimicrob Agents Chemother. 47(2), 739-746 (2003)).

  4. Can I dissolve Carithromycin, Product C9742, in DMSO?

    While we have not tested this ourselves, one publication mentions preparation of clarithromycin in DMSO at 100 mM.  Nagaya, T., et al., J. Clin. Invest., 106(3), 393-402 (2000).

  5. How should I store stock solutions of Carithromycin, Product C9742?

    While we have not tested solution stability ourselves, one reference indicates storage of stock solutions of clarithromycin at -20°C, with preparation of fresh stock solutions once a month. Reference: Chen, B. -M., et al., J. Pharm. Biomed. Anal., 42(4), 480-487 (2006).

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  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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Masahito Ogawa et al.
Journal of the American College of Cardiology, 51(20), 1977-1985 (2008-05-17)
Clarithromycin (CAM), a major macrolide antibiotic, has many biological functions, including matrix metalloproteinases (MMPs) regulation. However, little is known about the effect of CAM in heart transplantation via MMP-9. The purpose of this study was to clarify the role of
Ilknur Basyigit et al.
The Annals of pharmacotherapy, 38(9), 1400-1405 (2004-07-15)
Clarithromycin is an antimicrobial agent that can be used for treatment of chronic obstructive pulmonary disease (COPD) exacerbations with bronchodilator therapy. However, it has also been shown that clarithromycin has antiinflammatory effects by the inhibition of cytokine production. To evaluate
Barbara Gierlikowska et al.
Frontiers in pharmacology, 11, 1339-1339 (2020-10-06)
Phagocytosis is a crucial element of innate immune defense involved in bacterial killing. The aim of our study was to evaluate the influence of alantolactone on phagocytosis and cytokines release by THP1-derived macrophages. We assessed whether antimicrobial compound alantolactone (a
Shamira J Shallom et al.
Journal of clinical microbiology, 51(9), 2943-2949 (2013-06-28)
Mycobacterium abscessus (M. abscessus sensu lato, or the M. abscessus group) comprises three closely related taxa whose taxonomic statuses are under revision, i.e., M. abscessus sensu stricto, Mycobacterium bolletii, and Mycobacterium massiliense. We describe here a simple, robust, and cost-effective
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
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