sarecycline   Click here for help

GtoPdb Ligand ID: 12921

Synonyms: P005672 | Seysara®
Approved drug PDB Ligand
sarecycline is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Sarecycline is a tetracycline antibacterial with narrow-spectrum activity that was developed as an oral anti-acne therapeutic. Note that the structure shown here matches the CAS-assigned structure and is the same as the ChEMBL entry linked to below. The PubChem standardized chemical structure (CID 54681908) for sarecycline is represented with slightly different stereochemistry.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 173.86
Molecular weight 487.5
XLogP -0.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN(C)[C@H]1[C@]2([H])C[C@]3([H])CC4=C(C(=CC=C4CN(C)OC)O)C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=O)N)O)O
Isomeric SMILES O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)(C[C@]3(C(=C2O)C(=O)C=4C(C3)=C(CN(OC)C)C=CC4O)[H])[H]
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/h5-6,11,13,18,28,30-31,34H,7-9H2,1-4H3,(H2,25,33)/t11-,13-,18-,24-/m0/s1
InChI Key PQJQFLNBMSCUSH-SBAJWEJLSA-N
References
1. Deeks ED. (2019)
Sarecycline: First Global Approval.
Drugs, 79 (3): 325-329. [PMID:30659422]
2. Lomakin IB, Devarkar SC, Patel S, Grada A, Bunick CG. (2023)
Sarecycline inhibits protein translation in Cutibacterium acnes 70S ribosome using a two-site mechanism.
Nucleic Acids Res, 51 (6): 2915-2930. [PMID:36864821]
3. Zhanel G, Critchley I, Lin LY, Alvandi N. (2019)
Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris.
Antimicrob Agents Chemother, 63 (1). [PMID:30397052]