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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H45NO5S
Molecular Weight 507.726
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEFAMULIN

SMILES

C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CS[C@@H]4CC[C@@H](N)C[C@H]4O

InChI

InChIKey=KPVIXBKIJXZQJX-CSOZIWFHSA-N
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-/m0/s1

HIDE SMILES / InChI

Molecular Formula C28H45NO5S
Molecular Weight 507.726
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

LEFAMULIN is a pleuromutilin antibiotic under development for the treatment of community-acquired bacterial pneumonia, as well as acute bacterial skin and skin structure infections. It inhibits bacterial protein synthesis by binding to the peptidyl transferase center of the 50S ribosome, resulting in the cessation of bacterial growth.

Approval Year

PubMed

PubMed

TitleDatePubMed
Simultaneous assessment of the pharmacokinetics of a pleuromutilin, lefamulin, in plasma, soft tissues and pulmonary epithelial lining fluid.
2016 Apr

Sample Use Guides

In Vitro Use Guide
Lefamulin was evaluated against various Streptococcus pneumoniae serotypes that were collected from adults with lower respiratory tract infections. Lefamulin exhibited MIC50 and MIC90 values of 0.12 and 0.25 μg/ml, respectively, against the entire collection (n = 822). Similar results were obtained for lefamulin against each of the most common serotypes as well as against multidrug-resistant isolates and strains that are nonsusceptible to ceftriaxone or erythromycin.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:48:30 UTC 2019
Edited
by admin
on Mon Oct 21 19:48:30 UTC 2019
Record UNII
21904A5386
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEFAMULIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
LEFAMULIN [USAN]
Common Name English
ACETIC ACID, 2-(((1R,2R,4R)-4-AMINO-2-HYDROXYCYCLOHEXYL)THIO)-, (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
Systematic Name English
LEFAMULIN [WHO-DD]
Common Name English
(+)-LEFAMULIN
Common Name English
BC-3781
Code English
LEFAMULIN [INN]
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL3291398
Created by admin on Mon Oct 21 19:48:30 UTC 2019 , Edited by admin on Mon Oct 21 19:48:30 UTC 2019
PRIMARY
INN
9849
Created by admin on Mon Oct 21 19:48:30 UTC 2019 , Edited by admin on Mon Oct 21 19:48:30 UTC 2019
PRIMARY
PUBCHEM
25185057
Created by admin on Mon Oct 21 19:48:30 UTC 2019 , Edited by admin on Mon Oct 21 19:48:30 UTC 2019
PRIMARY
CAS
1061337-51-6
Created by admin on Mon Oct 21 19:48:30 UTC 2019 , Edited by admin on Mon Oct 21 19:48:30 UTC 2019
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY