LANOPEPDEN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H34FN7O4
Molecular Weight	479.5483
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12COCCN1CCN(C2)C3=C(F)C(NNC(=O)[C@H](CC4CCCC4)CN(O)C=O)=NC(C)=N3

InChI

InChIKey=SWHNZGMQMGFQGW-MSOLQXFVSA-N

InChI=1S/C22H34FN7O4/c1-15-24-20(19(23)21(25-15)29-7-6-28-8-9-34-13-18(28)12-29)26-27-22(32)17(11-30(33)14-31)10-16-4-2-3-5-16/h14,16-18,33H,2-13H2,1H3,(H,27,32)(H,24,25,26)/t17-,18+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67583947 | https://www.ncbi.nlm.nih.gov/pubmed/21918031 | https://www.ncbi.nlm.nih.gov/pubmed/23403431

LANOPEPDEN is an inhibitor of peptide deformylase, a bacterial enzyme required for protein maturation. It was in development for the treatment of complicated bacterial skin infection and hospitalized community-acquired pneumonia.

Approval Year

PubMed

Title	Date	PubMed
Antibiotics in development targeting protein synthesis.	2011 Dec	22191530
Determination of disk diffusion and MIC quality control ranges for GSK1322322, a novel peptide deformylase inhibitor.	2011 Nov	21918031
Single-dose safety, tolerability, and pharmacokinetics of the antibiotic GSK1322322, a novel peptide deformylase inhibitor.	2013 May	23403431
Comparative analysis of the antibacterial activity of a novel peptide deformylase inhibitor, GSK1322322.	2013 May	23478958

Patents

Sample Use Guides

In Vitro Use Guide

Lanopepden (GSK1322322) had an MIC90 of 1 μg/ml against M. catarrhalis and 4 μg/ml against H. influenzae, with 88.8% of beta-lactamase-positive strains showing growth inhibition at that concentration. All S. pneumoniae strains were inhibited by ≤ 4 μg/ml of GSK1322322, with an MIC90 of 2 μg/ml. GSK1322322 was very potent against S. pyogenes strains, with an MIC90 of 0.5 μg/ml, irrespective of their macrolide resistance phenotype. It was also active against S. aureus strains regardless of their susceptibility to methicillin, macrolides, or levofloxacin, with an MIC90 of 4 μg/ml in all cases.

Name

Type

Language

LANOPEPDEN

Official Name

English

lanopepden [INN]

Common Name

English

CYCLOPENTANEPROPANOIC ACID, .ALPHA.-((FORMYLHYDROXYAMINO)METHYL)-, 2-(5-FLUORO-6-((9AS)-HEXAHYDROPYRAZINO(2,1-C)(1,4)OXAZIN-8(1H)-YL)-2-METHYL-4-PYRIMIDINYL)HYDRAZIDE, (.ALPHA.R)-

Common Name

English

Lanopepden [WHO-DD]

Common Name

English

GSK-1322322B

Code

English

GSK-322

Code

English

LANOPEPDEN [USAN]

Common Name

English

GSK1322322

Code

English

GSK-1322322

Code

English

GSK1322322B

Code

English

Code System Code Type Description

USAN

BC-70