Structure via PubChem · Public domain (PubChem)
pleuromutilin
Sign in to saveAlso known as [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-hydroxyacetate
Pleuromutilin and its derivatives are antibacterial drugs that inhibit protein synthesis in bacteria by binding to the peptidyl transferase component of the 50S subunit of ribosomes.
Chemical data
- Formula
- C22H34O5
- Molecular weight
- 378.5 g/mol
- IUPAC name
- [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-hydroxyacetate
- SMILES
- C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CO)C
- InChIKey
- ZRZNJUXESFHSIO-BKUNHTPHSA-N
- XLogP
- 3.5
- Polar surface area
- 83.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
582 papers- Synthesis of Pleuromutilin.Journal of the American Chemical Society · 2022
- Lefamulin: The First Systemic Pleuromutilin Antibiotic.The Annals of pharmacotherapy · 2020
- Lefamulin: A Novel Semisynthetic Pleuromutilin Antibiotic for Community-acquired Bacterial Pneumonia.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2020
- Lefamulin: a promising new pleuromutilin antibiotic in the pipeline.Expert review of anti-infective therapy · 2019
- Pleuromutilin and its derivatives-the lead compounds for novel antibiotics.Mini reviews in medicinal chemistry · 2012
via PubMed
Wikidata facts
- Mass
- 378.2406241879999
Show 5 more facts
- topic's main category
- Category:Pleuromutilin antibiotics
- canonical SMILES
- CC12C(C)CCC3(CCC(=O)C23)C(C)C(O)C(C)(C=C)CC1OC(=O)CO
- isomeric SMILES
- C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CO)C
- chemical formula
- C₂₂H₃₄O₅
- Commons category
- Pleuromutilin
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- History
- Total synthesis
- Biosynthesis
- References
- Further reading
Pleuromutilin and its derivatives are antibacterial drugs that inhibit protein synthesis in bacteria by binding to the peptidyl transferase component of the 50S subunit of ribosomes.
This class of antibiotics includes the licensed drugs lefamulin (for systemic use in humans), retapamulin (approved for topical use in humans), valnemulin and tiamulin (approved for use in animals) and the investigational drug azamulin.
Excerpted from Wikipedia’s “pleuromutilin” article, available under the CC BY-SA 4.0 licence.