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;
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);
ECHA InfoCard	100.241.852
Chemical and physical data
Formula	C24H29N3O8
Molar mass	487.509 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)CN(C)OC;

Sarecycline is a narrow-spectrum tetracycline-derived antibiotic.^[1]^[2] 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.^[3] 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.^[3] Unlike other tetracycline-class antibiotics, sarecycline has a long C7 moiety that extends into and directly interact with the bacterial messenger RNA (mRNA).^[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] Sarecycline has not been tested in spirochetes.

References[]

^ Zhanel G, Critchley I, Lin LY, Alvandi N (January 2019). "Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris". Antimicrobial Agents and Chemotherapy. 63 (1). doi:10.1128/AAC.01297-18. PMC 6325184. PMID 30397052.
^ PubChem. "Sarecycline". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-09-05.
^ ^a ^b "FDA-approved Labeling-Package Insert for Seysara" (PDF). Drugs@FDA. June 2020. Retrieved September 5, 2020.
^ Moore, Angela; Green, Lawrence J.; Bruce, Suzanne; Sadick, Neil; Tschen, Eduardo; Werschler, Philip; Cook-Bolden, Fran E.; Dhawan, Sunil S.; Forsha, Douglass; Gold, Michael H.; Guenthner, Scott (2018-09-01). "Once-Daily Oral Sarecycline 1.5 mg/kg/day Is Effective for Moderate to Severe Acne Vulgaris: Results from Two Identically Designed, Phase 3, Randomized, Double-Blind Clinical Trials". Journal of Drugs in Dermatology. 17 (9): 987–996. ISSN 1545-9616. PMID 30235387.
^ Batool, Zahra; Lomakin, Ivan B.; Polikanov, Yury S.; Bunick, Christopher G. (2020-08-25). "Sarecycline interferes with tRNA accommodation and tethers mRNA to the 70S ribosome". Proceedings of the National Academy of Sciences. 117 (34): 20530–20537. doi:10.1073/pnas.2008671117. ISSN 0027-8424. PMC 7456112. PMID 32817463.
^ Zhanel, George; Critchley, Ian; Lin, Lynn-Yao; Alvandi, Nancy (2019-01-01). "Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris". Antimicrobial Agents and Chemotherapy. 63 (1). doi:10.1128/AAC.01297-18. ISSN 0066-4804. PMC 6325184. PMID 30397052.

External links[]

"Sarecycline". Drug Information Portal. U.S. National Library of Medicine.

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[1] Zhanel G, Critchley I, Lin LY, Alvandi N (January 2019). "Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris". Antimicrobial Agents and Chemotherapy. 63 (1). doi:10.1128/AAC.01297-18. PMC 6325184. PMID 30397052.

[2] PubChem. "Sarecycline". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-09-05.

[:0-3] "FDA-approved Labeling-Package Insert for Seysara" (PDF). Drugs@FDA. June 2020. Retrieved September 5, 2020.

[4] Moore, Angela; Green, Lawrence J.; Bruce, Suzanne; Sadick, Neil; Tschen, Eduardo; Werschler, Philip; Cook-Bolden, Fran E.; Dhawan, Sunil S.; Forsha, Douglass; Gold, Michael H.; Guenthner, Scott (2018-09-01). "Once-Daily Oral Sarecycline 1.5 mg/kg/day Is Effective for Moderate to Severe Acne Vulgaris: Results from Two Identically Designed, Phase 3, Randomized, Double-Blind Clinical Trials". Journal of Drugs in Dermatology. 17 (9): 987–996. ISSN 1545-9616. PMID 30235387.

[5] Batool, Zahra; Lomakin, Ivan B.; Polikanov, Yury S.; Bunick, Christopher G. (2020-08-25). "Sarecycline interferes with tRNA accommodation and tethers mRNA to the 70S ribosome". Proceedings of the National Academy of Sciences. 117 (34): 20530–20537. doi:10.1073/pnas.2008671117. ISSN 0027-8424. PMC 7456112. PMID 32817463.

[6] Zhanel, George; Critchley, Ian; Lin, Lynn-Yao; Alvandi, Nancy (2019-01-01). "Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris". Antimicrobial Agents and Chemotherapy. 63 (1). doi:10.1128/AAC.01297-18. ISSN 0066-4804. PMC 6325184. PMID 30397052.

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