Clarithromycin, USP

- Overview
  - Clarithromycin, USP is a macrolide antibiotic that is derivative of Erythromycin. This compound is both a substrate and inhibitor of CYP3A4. Clarithromycin has anti-cancer properties. Clarithromycin-related compounds are also available as highly pure EvoPure® products.
    Clarithromycin is slightly soluble in aqueous solution.
    Clarithromycin, USP conforms to United States Pharmacopeia specifications.
    
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    Background
    
    Macrolide antibiotics inhibit bacterial growth by targeting the 50S ribosomal subunit preventing peptide bond formation and translocation during protein synthesis. Resistance to Clarithromycin is commonly attributed to mutations in 50S rRNA preventing Clarithromycin binding allowing the cell to synthesize error-free proteins.
    Anti-cancer mechanisms include reduction of cytokines, inhibition of autophagy, and anti-angiogenesis. The compound can act on signal transduction pathways, transcription factors, drug pharmacokinetics, growth signals, and metastasis. These features can be exploited to make tumor cells more prone to apoptosis and reduce escape mechanisms. The mechanism used depend on the type of cancer.
- Properties
  - CAS Number
    
    81103-11-9
    
    Molecular Formula
    
    C38H69NO13
    
    Molecular Weight
    
    747.95
    
    Appearance
    
    White crystalline powder
    
    Other Properties
    
    Source: Semi-synthetic
    Water Content (Karl Fischer): ≤ 2.0%
    PH: 8.0-10.0
    Assay: 96.0-102.0% (on dried basis)
    Residue On Ignition: ≤ 0.2%
    Heavy Metals: ≤ 0.002%
    Optical Rotation: -94° to -102°
    
    Storage
    
    ≤ 30 °C
    
    * For research use only
- Applications
  - Application Description
    
    Spectrum: Clarithromycin is a broad-spectrum antibiotic with bacteriostatic action wide range of Gram-positive and Gram-negative bacteria including anaerobes. It is also effective for Mycoplasma and Mycobacteria.
    
    Microbiology Applications: Clarithromycin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options.
    Representative MIC values include:
    Haemophilus influenza 2 µg/mL - 32 µg/mL
    Streptococcus pneumoniae 0.12 µg/mL – 64 µg/mL
    Clarithromycin (TOKU-E) used in methacrylate-based copolymer films that released the compound (along with doxycycline and rifampicin) for up to 21 days were found to prevent biofilm formation when used in an in vitro bioreactor model (Rose et al, 2015).
    
    Eukaryotic Cell Culture Applications: An in vitro study on the inhibitory effect of Clarithromycin on transporter-expressing HEK-293 cell lines or membrane vesicles with 13 transporters (OATP1B1, OATP1B3, OAT1, OAT3, OCT1, OCT2, MATE1, MATE2-K, P-gp, BCRP, MRP2, MRP3, and BSEP) found that inhibition profiles were unique to the transporter (Vermeer et al, 2016). Macrolide antibiotics exert anti-inflammatory effects through inhibition of the production of proinflammatory cytokines. Nuclear factor kb (NF-kb) is an important transcription factor for genes that encode proinflammatory cytokines. In vitro studies with human monocytic leukemia cell line U-937, human T-cell leukemia (Jurkat), a pulmonary epithelial cell line A549, and peripheral blood mononuclear cells were conducted. Clarithromycin was found to suppress the production of proinflammatory cytokines via inhibition of NF-kb (Ichiyama T et al, 2001). Clarithromycin can have immunomodulatory activity on human lymphocyte function. The compound suppressed the synthesis of IL-1a, IL-1b, TNF-a, and GM-CSF in a concentration-dependent manner. This suggests Clarithromycin may modify the acute-phase inflammatory response by disturbing the cytokine cascade (Morikawa K et al, 1996).
    
    Cancer Applications: Clarithromycin is involved in autophagy-lysosome pathway. It can inhibit autophagy in myeloma and myeloid leukaemia cells. It inhibits lysosomal function after fusion of the autophagosomes with the lysosomes. Thus, it could be a potential adjuvant where autophagy is used by the tumor as an escape mechanism (Nakamura et al, 2010). The combined treatment of Clarithromycin with the proteasome inhibitor bortezomib enhances cytotoxicity in the breast cancer cell lines MDA-MB-231 and MDA-MB-468. A wild-type murine embryonic fibroblast (MEF) cell line also exhibited enhanced cytotoxicity (Komatsu et al, 2012). Direct antineplastic effects of CAM may depend on the tumor type. Researchers found a direct anti-tumor activity of CAM on lymphoma cells (Ochi et al, 2006) and it directly induced apoptosis in a murine B cell lymphoma cell line (Ohara et al, 2004).