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    Clarithromycin
    Clarithromycin

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0814
    CAS #: 81103-11-9Purity ≥98%

    Description: Clarithromycin (A56268; Abbott 56268; A 56268;  Abbott-56268; A-56268; trade name Biaxin) is an approved macrolide antibiotic medication acting as a CYP3A4 inhibitor. It has been widely used for treatment of a number of bacterial infections such as pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydophila pneumoniae), skin and skin structure infections. Clarithromycin prevents bacteria from growing by interfering with their protein synthesis. 

    References: J Antimicrob Chemother. 2002 May;49(5):745-55; Antimicrob Agents Chemother. 2001 Jan;45(1):44-7.

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    Molecular Weight (MW)747.95
    FormulaC38H69NO13
    CAS No.81103-11-9
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 25 mg/mL (33.4 mM)
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Other info

    Chemical Name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione

    InChi Key: AGOYDEPGAOXOCK-KCBOHYOISA-N

    InChi Code: 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 Code: CC[[email protected]@H]1[[email protected]@](C)(O)[[email protected]](O)[[email protected]@H](C)C([[email protected]](C)C[[email protected]@](C)(OC)[[email protected]](O[[email protected]]2[[email protected]](O)[[email protected]@H](N(C)C)C[[email protected]@H](C)O2)[[email protected]@H](C)[[email protected]](O[[email protected]]3C[[email protected]@](C)(OC)[[email protected]@H](O)[[email protected]](C)O3)[[email protected]@H](C)C(O1)=O)=O           

    SynonymsAbbott56268; A56268; A-56268; A 56268; A56268; Abbott 56268; A 56268; Clarithromycin; Abbott-56268; A-56268; brand name Biaxin. 


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    In Vitro

    In vitro activity: Clarithromycin suppresses this production in a dose-dependent manner in both monocytes and THP-1 cells. Clarithromycin regulates three other promoters that have either the NF-kappa B or the AP-1 binding sequences: two synthetic (pAP-1-Luc and pNF-kappa B-Luc) and one naturally occurring (ELAM-Luc). Clarithromycin suppresses NF-kappaB activation induced by TNF-alpha in U-937 and Jurkat cells in a concentration-related manner. Clarithromycin inhibits NF-kappaB activation induced by TNF-alpha in U-937, Jurkat, and A549 cells and PBMC and by SEA in PBMC. Clarithromycin prevents NF-kappaB-dependent reporter gene expression in U-937 cells. Clarithromycin results in a significant suppression of production of each cytokine in 71% and a significant increase in 29% of the human monocytes. Clarithromycin inhibits tumor necrosis factor (TNF)-alpha-induced IL-8 gene expression in a dose- and incubation time-dependent manner. Clarithromycin represses AP-1 binding in TNF-alpha-treated BET-1A cells. Clarithromycin represses IL-8 gene transcription mainly via the AP-1 binding site in human bronchial epithelial cells. Clarithromycin suppresses IL-1 beta gene expression in human nasal epithelial cells stimulated by H. influenzae endotoxin (HIE). Clarithromycin suppresses intercellular adhesion molecule-1 gene expression in nasal fibroblasts stimulated by IL-1 beta. Clarithromycin reduces DNA-binding activity of NF-kappa B in both human nasal epithelial cells and fibroblasts stimulated by HIE or IL-1 beta, respectively

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    References

    J Antimicrob Chemother. 2002 May;49(5):745-55; Antimicrob Agents Chemother. 2001 Jan;45(1):44-7.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Clarithromycin

    Representative flow-cytometric analysis demonstrating that pretreatment with clarithromycin significantly inhibited NF-κB activation induced by TNF-α in U-937 (A) and Jurkat cells (B) in a concentration-related manner.  Antimicrob Agents Chemother. 2001 Jan;45(1):44-7.



    Clarithromycin


    Representative Western blot demonstrating the effect of clarithromycin on TNF-α-induced IκBα degradation in A549 cells.
     

    Clarithromycin

    Representative Western blot of nuclear extracts of PBMC demonstrating that pretreatment with clarithromycin inhibited NF-κB activation induced by TNF-α or SEA in a concentration-dependent fashion. Antimicrob Agents Chemother. 2001 Jan;45(1):44-7.
     
     

    Clarithromycin

    Representative Western blot of nuclear extracts of PBMC demonstrating that pretreatment with clarithromycin inhibited NF-κB activation induced by TNF-α or SEA in a concentration-dependent fashion. Antimicrob Agents Chemother. 2001 Jan;45(1):44-7.



    Clarithromycin


    Representative Western blot of nuclear extracts of U-937, Jurkat, and A549 cells revealing that pretreatment with clarithromycin inhibited NF-κB activation induced by TNF-α in a concentration-dependent manner.


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