Oleandomycin

It used to be sold under the brand name Sigmamycine, combined with tetracycline, and made by the company Rosa-Phytopharma in France.

Like erythromycin, oleandomycin binds to the 50s subunit of bacterial ribosomes, inhibiting the completion of proteins vital to survival and replication.

[4] Oleandomycin is far less effective than erythromycin in bacterial minimum inhibitory concentration tests involving staphylococci or enterococci.

The polyketide chain is bound through thioester linkages to the S-H groups of the ACP and KS domains [citation needed] The amino acid sequence similarities between OLES and 6-Deoxyerythronolide B synthase (erythromycin precursor synthase) show only a 45% common identity.

[5] Oleandomycin was first discovered as a product of the bacterium Streptomyces antibioticus in 1954 by Dr. Sobin, English, and Celmer.

[7] Public interest in oleandomycin peaked when Pfizer introduced the combination drug Sigmamycine into the market in 1956.

Sigmamycine was a combination drug of oleandomycin and tetracycline that was supported by a major marketing campaign.

Polyketide Synthase Type I scheme of the synthesis of 8,8 deoxyoleanolide, the precursor to oleandomycin
Post-polyketide tailoring of 8,8' deoxyoleanolide to form oleandomycin