Pleuromutilin

Pleuromutilin
Names
Preferred IUPAC name
(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-Ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.316 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1 ☒N
    Key: ZRZNJUXESFHSIO-BKUNHTPHSA-N ☒N
  • 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
Properties
C22H34O5
Molar mass 378.509 g/mol
Melting point 170-171 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1][2]

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.[citation needed]

  1. ^ Maffioli, Sonia Ilaria (2013). "A chemist's survey of different antibiotic classes". In Gualerzi, Claudio O.; Brandi, Letizia; Fabbretti, Attilio; Pon, Cynthia L. (eds.). Antibiotics: Targets, Mechanisms and Resistance. Wiley-VCH. pp. 1–22. doi:10.1002/9783527659685.ch1. ISBN 978-3-527-65968-5. S2CID 11479628.
  2. ^ Eyal Z, Matzov D, Krupkin M, Paukner S, Riedl R, Rozenberg H, Zimmerman E, Bashan A, Yonath A (Dec 2016). "A novel pleuromutilin antibacterial compound, its binding mode and selectivity mechanism". Sci Rep. 6(39004): 39004. Bibcode:2016NatSR...639004E. doi:10.1038/srep39004. PMC 5154188. PMID 27958389.