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C9742
Clarithromycin
≥95% (HPLC)
Synonyme(s) :
6-O-methyl erythromycin
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About This Item
Formule empirique (notation de Hill):
C38H69NO13
Numéro CAS:
Poids moléculaire :
747.95
Numéro MDL:
Code UNSPSC :
51102829
ID de substance PubChem :
Nomenclature NACRES :
NA.76
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Produits recommandés
Niveau de qualité
Essai
≥95% (HPLC)
Forme
powder
Spectre d'activité de l'antibiotique
Gram-negative bacteria
Gram-positive bacteria
Mode d’action
protein synthesis | interferes
Chaîne SMILES
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
Clé InChI
AGOYDEPGAOXOCK-KCBOHYOISA-N
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Description générale
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.
Actions biochimiques/physiologiques
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.
Notes préparatoires
Practically insoluble in water, soluble in acetone and methylene chloride, slightly soluble in methanol.
Autres remarques
Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.
Mention d'avertissement
Warning
Mentions de danger
Conseils de prudence
Classification des risques
Acute Tox. 4 Oral
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 1
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
dust mask type N95 (US), Eyeshields, Gloves
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Certificats d'analyse (COA)
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Les clients ont également consulté
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
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
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
Stuart Schembri et al.
BMJ (Clinical research ed.), 346, f1235-f1235 (2013-03-26)
To study the association of clarithromycin with cardiovascular events in the setting of acute exacerbations of chronic obstructive pulmonary disease and community acquired pneumonia. Analysis of two prospectively collected datasets. Chronic obstructive pulmonary disease dataset including patients admitted to one
Jayaram Lakshmaiah Narayana et al.
Oncotarget, 6(15), 12936-12954 (2015-05-24)
Helicobacter pylori infection is marked by a strong association with various gastric diseases, including gastritis, ulcers, and gastric cancer. Antibiotic treatment regimens have low success rates due to the rapid occurrence of resistant H. pylori strains, necessitating the development of
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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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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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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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