nafithromycin   Click here for help

GtoPdb Ligand ID: 10834

Synonyms: WCK 4873 | WCK-4873 | WCK4873
Compound class: Synthetic organic
Comment: Nafithromycin (WCK-4873) is a ketolide antibacterial with Gram-positive activity [1-2].
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
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 15
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 252.42
Molecular weight 858.42
XLogP 3.44
No. Lipinski's rules broken 1
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.

✖
Canonical SMILES CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)[C@H]2/C(=N/O[C@H](c1nnc(s1)c1ccccn1)C)/N)C)C)(C)OC
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@@H]2[C@]1(C)OC(=O)[C@H]2/C(=N/O[C@H](c1nnc(s1)c1ccccn1)C)/N)C)C)(C)OC
InChI InChI=1S/C42H62N6O11S/c1-13-28-42(9)30(29(39(53)58-42)35(43)47-59-25(7)36-45-46-37(60-36)26-16-14-15-17-44-26)22(4)31(49)20(2)19-41(8,54-12)34(23(5)32(50)24(6)38(52)56-28)57-40-33(51)27(48(10)11)18-21(3)55-40/h14-17,20-25,27-30,33-34,40,51H,13,18-19H2,1-12H3,(H2,43,47)/t20-,21-,22-,23+,24-,25+,27+,28-,29-,30+,33-,34-,40+,41-,42-/m1/s1
InChI Key RLFCSBSRGRJFRO-QAOQTAGDSA-N
No information available.
Summary of Clinical Use Click here for help
Nafithromycin can be administered orally or parenterally. It has been advanced to Phase 2 clinical evaluation as treatment for community-acquired bacterial pneumonia (CABP).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03926962 The Safety, Tolerability And Pharmacokinetics Of Single Ascending Doses And The Effect Of Food On Oral WCK 4873 In Healthy Adult Volunteers Phase 1 Interventional Wockhardt 3
NCT02903836 Phase II Study of Oral Nafithromycin in CABP Phase 2 Interventional Wockhardt 3