Lefamulin

Lefamulin
Clinical data

ATC code	None
Legal status
Legal status	Investigational
Identifiers
IUPAC name (1S,2R,3S,4S,6R,7R,8R,14R)-3-Hydroxy-2,4,7,14-tetramethyl-9-oxo-4-vinyltricyclo[5.4.3.0^1,8]tetradec-6-yl {[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]sulfanyl}acetate
Synonyms	BC 3781
CAS Number	1061337-51-6
PubChem CID	25185057
ChemSpider	32701544
UNII	21904A5386
ChEMBL	CHEMBL3291398
Chemical and physical data
Formula	C₂₈H₄₅NO₅S
Molar mass	507.73 g·mol⁻¹
3D model (JSmol)	Interactive image
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)CS[C@@H]4CC[C@H](C[C@H]4O)N)C
InChI InChI=1S/C28H45NO5S/c1-6-26(4)14-22(34-23(32)15-35-21-8-7-18(29)13-20(21)31)27(5)16(2)9-11-28(17(3)25(26)33)12-10-19(30)24(27)28/h6,16-18,20-22,24-25,31,33H,1,7-15,29H2,2-5H3/t16-,17+,18-,20-,21-,22-,24+,25+,26-,27+,28+/m1/s1 Key:KPVIXBKIJXZQJX-FCEONZPQSA-N

Lefamulin is a pleuromutilin antibiotic that is being developed by Nabriva Therapeutics for the treatment of acute bacterial skin and skin-structure infections (ABSSSI).^[1] It was granted fast track status by the US Food and Drug Administration in 2014. As of May 2016, it is in phase III clinical trials.^[2]

Spectrum of activity

↑ Zeitlinger, M; Schwameis, R; Burian, A; Burian, B; Matzneller, P; Müller, M; Wicha, W. W.; Strickmann, D. B.; Prince, W (2016). "Simultaneous assessment of the pharmacokinetics of a pleuromutilin, lefamulin, in plasma, soft tissues and pulmonary epithelial lining fluid". Journal of Antimicrobial Chemotherapy. 71 (4): 1022–6. PMID 26747098. doi:10.1093/jac/dkv442.
1 2 H. Spreitzer (23 May 2016). "Neue Wirkstoffe - Lefamulin". Österreichische Apothekerzeitung (in German) (11/2016).
↑ Mendes, R. E.; Farrell, D. J.; Flamm, R. K.; Talbot, G. H.; Ivezic-Schoenfeld, Z; Paukner, S; Sader, H. S. (2016). "In vitro activity of lefamulin tested against Streptococcus pneumoniae with defined serotypes, including multidrug-resistant isolates causing lower respiratory tract infections in the United States". Antimicrobial Agents and Chemotherapy. 60: AAC.00627–16. PMID 27161634. doi:10.1128/AAC.00627-16.

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