A pleuromutilin antibiotic
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Lefamulin

Item No. 36285

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(1R,2R,4R)-4-amino-2-hydroxycyclohexyl]thio]-acetic acid, (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
CAS Number
1061337-51-6
Synonyms
  • BC-3781
Molecular Formula
C28H45NO5S
Formula Weight
507.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mLDMSO: 12 mg/mLEthanol: 3 mg/mLPBS (pH 7.2): 0.25 mg/mL
SMILES
O=C1CC[C@@]2(CC[C@H]3C)[C@@H](C)[C@H](O)[C@@](C=C)(C)C[C@@H](OC(CS[C@@H]4CC[C@@H](N)C[C@H]4O)=O)[C@@]3(C)[C@@]21[H]
InChi Code
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
InChi Key
KPVIXBKIJXZQJX-FCEONZPQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Lefamulin is a pleuromutilin antibiotic.1 It is active against methicillin-resistant S. aureus (MRSA), S. pyogenes, E. faecium, H. influenzae, M. catarrhalis, L. pneumonophilia, C. pneumoniae, and M. pneumoniae (MIC50s = 0.006-1 µg/ml). Lefamulin is also active against fluoroquinolone- and macrolide-resistant strains of N. gonorrhoeae (MIC90s = 1 mg/L for all). In vivo, lefamulin (10-40 mg/kg) reduces the number of colony-forming units (CFUs) in a mouse model of S. pneumoniae thigh infection.2 It also reduces LPS-induced production of TNF-α, IL-6, IL-1β, and GM-CSF, bronchoalveolar lavage fluid (BALF) neutrophil infiltration, and lung matrix metalloproteinase-9 (MMP-9) levels in a mouse model of LPS-induced neutrophilia.3 Formulations containing lefamulin have been used in the treatment of community-acquired bacterial pneumonia (CABP).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Veve, M.P., and Wagner, J.L. Lefamulin: Review of a promising novel pleuromutilin antibiotic. Pharmacotherapy 38(9), 935-946 (2018).

    2. Wicha, W.W., Craig, W.A., and Andes, D. In vivo pharmacodynamics of lefamulin, the first systemic pleuromutilin for human use, in a neutropenic murine thigh infection model. J. Antimicrob. Chemother. 74(Suppl 3), iii5-iii10 (2019).

    3. Hafner, M., Paukner, S., Wicha, W.W., et al. Anti-inflammatory activity of lefamulin versus azithromycin and dexamethasone in vivo and in vitro in a lipopolysaccharide-induced lung neutrophilia mouse model. PLoS One 16(9), e0237659 (2022).