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
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Sarecycline is indicated for the treatment of moderate to severe cases of inflammatory lesions of non-nodular acne vulgaris. Sarecycline hydrochloride, as an oral formulation under the trade name Seysara®, was granted first approval by the US FDA in October 2018 [1].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Sarecycline inhibits protein synthesis in the bacterial ribosome and has been shown to bind to two active sites on the 70S ribosome of Cutibacterium acnes [2].
External links Click here for help
For extended ADME data see the following:

Drugs.com