Sarecycline

Sarecycline
Clinical data
Pronunciation	sar"e sye' kleen
Trade names	Seysara
Other names	P-005672
AHFS/Drugs.com	Monograph
MedlinePlus	a618068
License data	US DailyMed: Sarecycline;
Routes of; administration	By mouth
ATC code	J01AA14 (WHO) J01AA20 (WHO);
Legal status
Legal status	US: ℞-only;
Identifiers
	IUPAC name (4S,4aS,5aR,12aR)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-7-{[methoxy(methyl)amino]methyl}-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;
CAS Number	1035654-66-0;
PubChem CID	54681908; as HCl: 71296095;
DrugBank	DB12035; as HCl: DBSALT002125;
ChemSpider	28540486;
UNII	94O110CX2E;
KEGG	D10666; as HCl: D10667;
ChEMBL	ChEMBL2364632;
PDB ligand	V7A (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID001027924 ;
ECHA InfoCard	100.241.852
Chemical and physical data
Formula	C24H29N3O8
Molar mass	487.509 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CON(C)Cc1ccc(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]3(O)C(=O)C1=C2O;
	InChI InChI=1S/C24H29N3O8/c1-26(2)18-13-8-11-7-12-10(9-27(3)35-4)5-6-14(28)16(12)19(29)15(11)21(31)24(13,34)22(32)17(20(18)30)23(25)33/h5-6,11,13,18,28-29,32,34H,7-9H2,1-4H3,(H2,25,33)/t11-,13-,18-,24-/m0/s1; Key:AYUMVPHUMFKFPJ-SBAJWEJLSA-N;

Sarecycline, sold under the brand name Seysara, is a narrow-spectrum tetracycline-derived antibiotic medication.^[2]^[3] 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.^[1] Two randomized and well-controlled clinical trials reported efficacy data on both facial and truncal acne (back and chest).^[4] Efficacy was assessed in a total of 2002 subjects 9 years of age and older.^[1] 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.^[5] 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.^[6]