Clarithromycin, USP

81103-11-9

C38H69NO13

747.95

White crystalline powder

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°

≤ 30 °C

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).