Clarithromycin A macrolide antibiotic and protein synthesis inhibitor

Clarithromycin (CAS 81103-11-9)

Clarithromycin | CAS 81103-11-9 is rated 5.0 out of 5 by 1.
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Synonym: Biaxin; Cyllind; Klacid
Application: A macrolide antibiotic and protein synthesis inhibitor
CAS Number: 81103-11-9
Purity: ≥98%
Molecular Weight: 747.95
Molecular Formula: C38H69NO13
* Refer to Certificate of Analysis for lot specific data (including water content).
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Clarithromycin is a 14-member ring macrolide antibiotic and 6-O-methyl derivative of erythromycin. Clarithromycin has reported bacteriostatic action against gram-positive bacteria and some gram-negative bacteria including anaerobes. Similar to other macrolide antibiotics, this antibiotic is believed to function via binding of the ribosome within the microorganism. Studies have noted that Clarithromycin appears to bind specifically to the 50S ribosomal subunit, thus inhibiting DNA translation and inhibiting bacterial growth. This compound is both a substrate and inhibitor of CYP3A4.


References

1. Goldman, R.C., et al. 1994. Antimicrob. Agents Chemother. 38: 1496-1500. PMID: 7979278
2. Champney, W.S. and Miller, M. 2002. Curr. Microbiol. 44: 418-424. PMID: 12000992
3. Mamelli, L., et al. 2005. J. Antimicrob. Chemother. 56: 491-497. PMID: 16055509
4. Sadeghi-Khomami, A., et al. 2008. Chem. Biol. 15: 739-749. PMID: 18635010

Appearance :
Crystalline powder
Physical State :
Solid
Solubility :
Soluble in ethanol (<1 mg/ml), water (<1 mg/ml), acetone (50 mg/ml), DMSO (18 mg/ml), and methanol.
Storage :
Store at room temperature
Melting Point :
222-231° C
Boiling Point :
805.48° C at 760 mmHg (Predicted)
Density :
1.18 g/cm3 (Predicted)
Refractive Index :
n20D 1.53 (Predicted)
Optical Activity :
α20/D -92°, c = 1 in chloroform
IC50 :
Streptococcus pneumoniae 5635: IC50 = 90 nM; Mdr-1: IC50 = 3.8 µM (human); Toxoplasma gondii 2F-1 expressing yellow fluorescent protein infected : IC50 = 31 µM; HERG: IC50 = 33.1 µM (human)
Ki Data :
CYP3A4: Ki= 5.49 µM (human)
pK Values :
pKa: 13.08 (Predicted), 8.16 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
KF4997000
PubChem CID :
84029
Merck Index :
14: 2239
MDL Number :
MFCD00865140
Beilstein Registry :
3581974
SMILES :
CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)C(O)C(C)O2)[C@H](C)[C@@H](OC2OC(C)CC(C2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O)OC

Download SDS (MSDS)

Certificate of Analysis

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What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. Clarithromycin, sc-205634, is a white or almost white crystalline powder.
Answered by: TechService7
Date published: 2017-01-27
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Rated 5 out of 5 by from Sadeghi Sadeghi-Khomami et al. (PubMed ID 18635010) found that clarithromycin was a competitive inhibitor of glycosidase. -SCBT Publication Review
Date published: 2015-01-18
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