LIPID MAPS

Clarithromycin is a polyketide synthase-derived semisynthetic macrolide antibiotic.^1,2,3 It is active against methicillin-susceptible, but not methicillin-resistant, S. aureus (MIC50s = 0.06 and >128 µg/ml), S. pyogenes, L. monocytogenes, and B. pertussis (MIC50 = 0.015, 0.25, and ≤0.008 µg/ml, respectively), among others.¹ Clarithromycin (25 mg/kg) decreases the number of colony-forming units (CFUs) in the spleen in a mouse model of M. avium infection.⁴ Formulations containing clarithromycin have been used in the treatment of bacterial infections.

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References

1. Wilson, D.N. The A-Z of bacterial translation inhibitors. Crit. Rev. Biochem. Mol. Biol. 44(6), 393-433 (2009).

2. Hardy, D.J., Hensey, D.M., Beyer, J.M., et al. Comparative in vitro activities of new 14-, 15-, and 16-membered macrolides. Antimicrob. Agents Chemother. 32(11), 1710-1719 (1988).

3. Wu, J., Kinoshita, K., Khosla, C., et al. Biochemical analysis of the substrate specificity of the β-ketoacyl-acyl carrier protein synthase domain of module 2 of the erythromycin polyketide synthase. Biochemistry 43(51), 16301-16310 (2004).

4. Fernandes, P.B., Hardy, D.J., McDaniel, D., et al. In vitro and in vivo activities of clarithromycin against Mycobacterium avium. Antimicrob. Agents Chemother. 33(9), 1531-1534 (1989).

String Representations

InChiKey (Click to copy)

AGOYDEPGAOXOCK-KCBOHYOISA-N

InChi (Click to copy)

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 (Click to copy)

[C@@H]1(O[C@@H]2O[C@@H](C[C@H](N(C)C)[C@H]2O)C)[C@@H](C)[C@@H]([C@@H](C)C(=O)O[C@@H]([C@](O)(C)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)CC)O[C@@H]1O[C@H]([C@H](O)[C@](C)(OC)C1)C