Pleuromutilin
| Pleuromutilin | ||
|---|---|---|
 | ||
| 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 | ||
| CAS number | 125-65-5  | |
| PubChem | 31326 | |
| ChEMBL | CHEMBL497295  | |
| Jmol-3D images | Image 1 | |
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| Properties | ||
| Molecular formula | C22H34O5 | |
| Molar mass | 378.502 g/mol | |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| 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 retapamulin (licenced for topical use in humans), valnemulin and tiamulin (approved for use in animals) and the investigational drugs azamulin and BC-3781.
History
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
- ↑ Long, Katherine S (April 2006). "Interaction of Pleuromutilin Derivatives with the Ribosomal Peptidyl Transferase Center". Antimicrobial Agents and Chemotherapy 50 (4): 1458–1462. doi:10.1128/AAC.50.4.1458-1462.2006. PMC 1426994. PMID 16569865.
- ↑ 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.
- ↑ 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.
- ↑ Kilaru, Sreedhar; Catherine M. Collins, Amanda J. Hartley, Andy M. Bailey, and 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.
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