Pleuromutilin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Pleuromutilin
Pleuromutilin skeletal.svg
Names
IUPAC name
(4R,5S,6S,8R,9aR,10R)-6-Ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate
Identifiers
125-65-5 YesY
ChEMBL ChEMBL497295 N
Jmol-3D images Image
PubChem 31326
Properties
C22H34O5
Molar mass 378.509 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

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 retapamulin (approved for topical use in humans), valnemulin and tiamulin (approved for use in animals) and the investigational drugs azamulin and lefamulin (BC-3781).

History[edit]

Pleuromutilin was first discovered as an antibiotic in 1950.[3] It is derived from the fungus Clitopilus passeckerianus (formerly Pleurotus passeckerianus), and has also been found in Drosophila subatrata, Clitopilus scyphoides, and some other Clitopilus species.[4]

References[edit]

  1. ^ Long, Katherine S; Lykke H. Hansen; Lene Jakobsen; Birte Vester (April 2006). "Interaction of Pleuromutilin Derivatives with the Ribosomal Peptidyl Transferase Center" (PDF). Antimicrobial Agents and Chemotherapy 50 (4): 1458–1462. doi:10.1128/AAC.50.4.1458-1462.2006. PMC 1426994. PMID 16569865. 
  2. ^ Lolk, L.; Pøhlsgaard, J.; Jepsen, A. S.; Hansen, L. H.; Nielsen, H.; Steffansen, S. I.; Sparving, L.; Nielsen, A. B.; Vester, B.; Nielsen, P. (2008). "A Click Chemistry Approach to Pleuromutilin Conjugates with Nucleosides or Acyclic Nucleoside Derivatives and Their Binding to the Bacterial Ribosome". Journal of Medicinal Chemistry 51 (16): 4957–4967. doi:10.1021/jm800261u. PMID 18680270.  edit
  3. ^ Novak, R; Shlaes DM (February 2010). "The pleuromutilin antibiotics: a new class for human use". Current Opinion in Investigational Drugs 11 (2): 182–91. PMID 20112168. 
  4. ^ Kilaru, Sreedhar; Catherine M. Collins; Amanda J. Hartley; Andy M. Bailey; Gary D. Foster (2009-09-18). "Establishing Molecular Tools for Genetic Manipulation of the Pleuromutilin-Producing Fungus Clitopilus passeckerianus". Appl Environ Microbiol (American Society for Microbiology) 75 (22): 7196–7204. doi:10.1128/AEM.01151-09. PMC 2786515. PMID 19767458.