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C9742
Clarithromycin
≥95% (HPLC)
Synonym(s):
6-O-methyl erythromycin
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About This Item
Empirical Formula (Hill Notation):
C38H69NO13
CAS Number:
Molecular Weight:
747.95
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.76
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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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Related Categories
1 of 4
This Item | A3487 | PHR1038 | Y0000320 |
|---|---|---|---|
| antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria | antibiotic activity spectrum - | antibiotic activity spectrum - |
| mode of action protein synthesis | interferes | mode of action protein synthesis | interferes | mode of action - | mode of action - |
| Quality Level 200 | Quality Level 200 | Quality Level 300 | Quality Level - |
| assay ≥95% (HPLC) | assay 96.0-102.0% (HPLC) | assay - | assay - |
| form powder | form powder | form - | form - |
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[1]. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD)[2]. 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.
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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What is the Department of Transportation shipping information for this product?
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I want to use Carithromycin, Product C9742, in cell culture. What solvent can I use?
1 answer-
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)).
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How should I store stock solutions of Carithromycin, Product C9742?
1 answer-
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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Can I dissolve Carithromycin, Product C9742, in DMSO?
1 answer-
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).
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