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C9742

Sigma-Aldrich

Clarithromycin

≥95% (HPLC)

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Synonym(s):
6-O-methyl erythromycin
Empirical Formula (Hill Notation):
C38H69NO13
CAS Number:
Molecular Weight:
747.95
MDL number:
PubChem Substance ID:

Quality Level

assay

≥95% (HPLC)

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

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

InChI key

AGOYDEPGAOXOCK-KCBOHYOISA-N

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This Item
PHR1038A3487Y0000320
vibrant-m

C9742

Clarithromycin

vibrant-m

PHR1038

Clarithromycin

vibrant-m

A3487

Clarithromycin

vibrant-m

Y0000320

Clarithromycin

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

-

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

-

form

powder

form

-

form

powder

form

-

assay

≥95% (HPLC)

assay

-

assay

96.0-102.0% (HPLC)

assay

-

General description

Chemical structure: macrolide

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.

Preparation Note

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

Other Notes

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

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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
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

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