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
CAS Number	125-65-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL497295 ;
ChemSpider	8061754 ;
ECHA InfoCard	100.004.316
KEGG	C09169 ;
PubChem CID	9886081;
UNII	3DE4A80MZ1 ;
CompTox Dashboard (EPA)	DTXSID9048720 ;
	InChI 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 Key: ZRZNJUXESFHSIO-BKUNHTPHSA-N ;
	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;
Properties
Chemical formula	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). verify (what is ?) 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 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.

^ 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.
^ 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.

[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.

[pmid27958389-2] 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.

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