telithromycin (ketek) Report issue

Small molecule Approved FDA
AACT ChEMBL DrugBank Drug Central Drugs@FDA KEGG MeSH PubChem repoDB

Active Ingredient History

NOW
  • Now
French pharmaceutical company Hoechst Marion Roussel (later Sanofi-Aventis) began phase II/III clinical trials of telithromycin (HMR-3647) in 1998. Telithromycin was approved by the European Commission in July 2001 and subsequently went on sale in October 2001. In the US, telithromycin received U.S. Food and Drug Administration (FDA) approval on April 1, 2004 Telithromycin is the first ketolide antibiotic to enter clinical use and is sold under the brand name of Ketek. After significant controversy regarding safety and research fraud, the US Food and Drug Administration sharply curtailed the approved uses of the drug in 2007. Telithromycin is a semi-synthetic erythromycin derivative. It is created by substituting a ketogroup for the cladinose sugar and adding a carbamate ring in the lactone ring. An alkyl-aryl moiety is attached to this carbamate ring. Furthermore, the carbon at position 6 has been methylated, as is the case in clarithromycin, to achieve better acid-stability. For the treatment of Pneumococcal infection, acute sinusitis, acute bacterial tonsillitis, acute bronchitis and bronchiolitis, lower respiratory tract infection and lobar (pneumococcal) pneumonia. KETEK tablets contain telithromycin, a semisynthetic antibacterial in the ketolide class for oral administration. Telithromycin blocks protein synthesis by binding to domains II and V of 23S rRNA of the 50S ribosomal subunit. By binding at domain II, telithromycin retains activity against gram-positive cocci (e.g., Streptococcus pneumoniae) in the presence of resistance mediated by methylases (erm genes) that alter the domain V binding site of telithromycin. Telithromycin may also inhibit the assembly of nascent ribosomal units.   NCATS

Chemistry

  • 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[C@@H](C)C(=O)[C@H](C)[C@H]3N(CCCCN4C=NC(=C4)C5=CC=CN=C5)C(=O)O[C@]13C)OC
  • InChIKey: LJVAJPDWBABPEJ-PNUFFHFMSA-N
  • Mol. Mass: 812.0037
  • ALogP: 4.93
  • ChEMBL Molecule:
    telithromycin  
More Chemistry

Pharmacology

Alternative names

hmr3647 | hmr 3647 | hmr-3647 | ketek | ru 66647 | ru-66647 | telithromycin

Organizations (10)

Research & Development (9)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Marketing (2)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Indications (17)

Approved Indications (4)


 

Bronchitis, Chronic (approved 2004)

Pneumonia

Pneumonia, Bacterial (approved 2004)

Sinusitis (approved 2004)

Experimental Indications - Clinical Trial Phases 1-4 (17)


 

Asthma (Phase 3)

Bronchitis (Phase 4)

Bronchitis, Chronic (Phase 4)

Child (Phase 3)

Community-Acquired Infections (Phase 4)

Healthy Volunteers (Phase 4)

Infections (Phase 3)

Maxillary Sinusitis (Phase 4)

Otitis Media (Phase 3)

Otitis Media, Suppurative (Phase 3)

Pharyngitis (Phase 3)

Pneumonia ()

Pneumonia, Bacterial (Phase 4)

Respiratory Tract Infections (Phase 4)

Scrub Typhus (Phase 3)

Sinusitis (Phase 4)

Tonsillitis (Phase 3)

Overview

  • Highest Phase: Phase 4
  • # of Trials: 24
  • # of Trial Organizations: 9

Trials by Phase

Trial Phase Start Date Organizations Indications

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