GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

LFF571   Click here for help

GtoPdb Ligand ID: 14344

Synonyms: J3.333.591A | LFF 571 | LFF-571
Compound class: Peptide
Comment: LFF571 is a macrocyclic thiopetide with activity against Gram-positive bacteria and derived from the naturally occurring antibacterial GE2270 A [2]. Functionally, it inhibits bacterial protein synthesis by targeting elongation factor Tu (EF-Tu) [3]. Note that the structure shown here matches the CAS-assigned structure. The PubChem link, provided in the table below, is to their standardized chemical structure (CID 42638236), although this is not an exact structural match.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CC(C)[C@H]1C2=NC(=C(COC)S2)C(=O)NCC(=O)N[C@@]([H])([C@H](C3=CC=CC=C3)O)C4=NC(=CS4)C5=NC(=CS5)C6=NC(=CC=C6C7=NC(=CS7)C(=O)N[C@@H](CC(=O)NC)C8=NC(=C(C)S8)C(=O)N1)C9=NC(=CS9)N(CCCCC(=O)O)C(=O)O[C@H]%10CC[C@@H](CC%10)C(=O)O
Isomeric SMILES O=C1C=2N=C(C=3C(C=4N=C(SC4)C=5N=C(SC5)[C@]([C@@H](O)C6=CC=CC=C6)(NC(=O)CNC(=O)C7=C(COC)SC([C@H](C(C)C)NC(=O)C=8N=C([C@H](CC(NC)=O)N1)SC8C)=N7)[H])=NC(=CC3)C9=NC(N(C(O[C@@H]%10CC[C@@H](C(O)=O)CC%10)=O)CCCCC(O)=O)=CS9)SC2
InChI InChI=1S/C60H63N13O13S6/c1-28(2)44-58-72-47(39(92-58)23-85-5)51(80)62-22-42(75)69-48(49(78)30-11-7-6-8-12-30)57-67-38(26-89-57)55-65-36(24-88-55)46-33(53-66-37(25-87-53)50(79)64-35(21-41(74)61-4)56-71-45(29(3)91-56)52(81)70-44)18-19-34(63-46)54-68-40(27-90-54)73(20-10-9-13-43(76)77)60(84)86-32-16-14-31(15-17-32)59(82)83/h6-8,11-12,18-19,24-28,31-32,35,44,48-49,78H,9-10,13-17,20-23H2,1-5H3,(H,61,74)(H,62,80)(H,64,79)(H,69,75)(H,70,81)(H,76,77)(H,82,83)/t31-,32-,35-,44-,48-,49-/m0/s1
InChI Key GNLYKLDXQZHYTR-LMOGNUDZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
LFF571 was being developed by Novartis as an oral treatment for Clostridium difficile infections. However, this appears to have ceased with the decision by the company in 2018 to drop its antibacterial and antiviral research programs. Results from a Phase 2 clinical trial (NCT01232595), reported that LFF571 was effective and well tolerated when used for the treatment of moderate C. difficile infections [4] and that it is retained in the lumen of the gastrointestinal tract [1].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01232595 Safety and Efficacy of Multiple Daily Dosing of Oral LFF571 in Patients With Moderate Clostridium Difficile Infections Phase 2 Interventional Novartis 1,4