Sarecycline, sold under the brand name Seysara, is a narrow-spectrum tetracycline-derived antibiotic medication. It is specifically designed for the treatment of acne, and was approved by the FDA in October 2018 for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris in patients 9 years of age and older. Two randomized and well-controlled clinical trials reported efficacy data on both facial and truncal acne (back and chest). Efficacy was assessed in a total of 2002 subjects 9 years of age and older. Unlike other tetracycline-class antibiotics, sarecycline has a long C7 moiety that extends into and directly interact with the bacterial messenger RNA (mRNA) via hydrogen bonding of the oxygen atom in the N-oxide moiety to nucleotide residues. The spectrum of activity is limited to clinically relevant Gram-positive bacteria, mainly Cutibacterium acnes, with little or no activity against Gram-negative bacterial microflora commonly found in the human gastrointestinal tract.
Sarecycline, is indicated for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris.
The chemical synthesis of sarecycline was reported:
The iodination of sancycline [808-26-4] (1) with N-iodosuccinimide gave 7-iodotetracycline [113164-67-3] (2). Carbonylation catalyzed by palladium acetate and Xantphos followed by treatment with triethylsilane provided the corresponding aldehyde [1035655-10-7] (3). Reductive amination with methoxymethylamine [1117-97-1] using sodium cyanoborohydride as the reductant provided an overall yield of 23% of sarecycline (4).