Lanopepden (formerly known as GSK 1322322 and GSK-322) is a novel, potent and selective peptide deformylase inhibitor with activity against Staphylococcus aureus strains with MICs of 1 and 1 mg/L for ATCC 29213 and ATCC 25923 strain, respectively. It has good in vitro activity against bacteria associated with community-acquired pneumonia and skin infections. Lanopepden had bactericidal activity against S. pneumoniae, H. influenzae, S. pyogenes, and S. aureus, demonstrating a ≥ 3-log(10) decrease in the number of CFU/ml at 4× MIC within 24 h in 29 of the 33 strains tested. Lanopepden represents a valuable alternative therapy for the treatment of infectious diseases caused by drug-resistant pathogens.
Physicochemical Properties
| Molecular Formula | C22H34N7O4F |
| Molecular Weight | 479.54826 |
| Exact Mass | 479.266 |
| Elemental Analysis | C, 55.10; H, 7.15; F, 3.96; N, 20.45; O, 13.34 |
| CAS # | 1152107-25-9 |
| Related CAS # | 1441390-17-5 (mesylate);1152107-25-9;1441390-22-2 (2 mesylate);1441390-28-8 (camsylate); |
| PubChem CID | 52918384 |
| Appearance | Solid powder |
| LogP | 2.484 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 34 |
| Complexity | 686 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | O=CN(C[C@@H](CC1CCCC1)C(NNC2=NC(C)=NC(N3C[C@@]4([H])COCCN4CC3)=C2F)=O)O |
| InChi Key | SWHNZGMQMGFQGW-MSOLQXFVSA-N |
| InChi Code | 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 |
| Chemical Name | N-[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro- 6-[(9aS)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]- 2-methylpyrimidin-4-yl}hydrazin-1-yl)-3-oxopropyl]- N-hydroxyformamide |
| Synonyms | GSK-322; GSK322; GSK 322; GSK-1322322; GSK1322322; GSK 1322322; GSK-1322322B; GSK-1322322J; GSK 1322322B |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References | Antimicrob Agents Chemother.2015 Sep;59(9):5747-60. |
| Additional Infomation | Lanopepden has been used in trials studying the treatment of Pneumonia, Infections, Bacterial, Skin Diseases, Infectious, and Skin Infections, Bacterial. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~30 mg/mL (~62.56 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (6.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0853 mL | 10.4264 mL | 20.8529 mL | |
| 5 mM | 0.4171 mL | 2.0853 mL | 4.1706 mL | |
| 10 mM | 0.2085 mL | 1.0426 mL | 2.0853 mL |