C9742 Sigma-Aldrich


≥95% (HPLC)



Related Categories A - K, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics  A-F,
Quality Level   200
assay   ≥95% (HPLC)
form   powder
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
SMILES string   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


General description

Chemical structure: macrolide


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. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD). It is used to study bacterial protein synthesis and peptide translation.

Biochem/physiol Actions

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.

Preparation Note

Practically insoluble in water, soluble in acetone and methylene chloride, slightly soluble in methanol.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Safety & Documentation

Safety Information

GHS07  GHS07
Signal word 
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
I want to useCarithromycin, Product C9742, in cell culture.What solvent can I use?
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)).
Can I dissolveCarithromycin, Product C9742, in DMSO?
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).
How should I store stock solutions of Carithromycin, Product C9742?
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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What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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