Compound ID | 140

Update compound information

Nafithromycin

Synonym(s): WCK 4873

Class: Macrolide

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to domains II and V of 23S rRNA to circumvent resistance mechanisms impacting older macrolide due to their single target binding
Target Pathogen: Active against pathogen causing community-acquired bacterial pneumonia
Description: A 16-membered macrolide/ ketolide; derivative of clarithromycin
Institute where first reported: Wockhardt, India
Year first mentioned: 2013
Highest development stage: Approved in India
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 859.04
Iso. SMILES: CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)[C@@H](C(=O)O2)/C(=N/O[C@@H](C)C4=NN=C(S4)C5=CC=CC=N5)/N)C
InChI Key: RLFCSBSRGRJFRO-QAOQTAGDSA-N
Can. SMILES: CC[C@@H]1[C@]2(C)[C@@H]([C@@H](C)C(=O)[C@H](C)C[C@](C)([C@@H]([C@@H](C)C(=O)[C@@H](C)C(=O)O1)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)OC)[C@H](/C(=N/O[C@@H](C)C4=NN=C(C5=NC=CC=C5)S4)/N)C(=O)O2
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/117587595
Guide to Pharmacology: nafithromycin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/40833448/
  • https://link.springer.com/article/10.1007/s00044-024-03281-5
  • https://doi.org/10.1007/s00044-023-03101-2

    • AntibioticDB is supported by GARDP.

    If you have feedback, experience problems, or are interested in a collaboration, please contact us. | Terms and conditions

    The content of this site is intended for educational and scientific research purposes only and not as a source of medical advice or consultation.