telithromycin   Click here for help

GtoPdb Ligand ID: 10878

Synonyms: HMR-3647 | Ketek® | Levviax® | RU-66647 | RU66647
Approved drug
telithromycin is an approved drug (EMA (2001), FDA (2004))
Compound class: Synthetic organic
Comment: Telithromycin is a ketolide antibiotic [1-2,4].
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 14
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 171.85
Molecular weight 811.47
XLogP 3.03
No. Lipinski's rules broken 2
Click here for help
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)N2CCCCn1cnc(c1)c1cccnc1)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)N2CCCCn1cnc(c1)c1cccnc1)C)C)(C)OC
InChI InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37+,38-,40+,42-,43-/m1/s1
No information available.
Summary of Clinical Use Click here for help
Telithromycin has been used to treat infections caused by Gram-positive bacteria, such as sinusitis, tonsillitis, bronchitis, chronic pharyngitis, community-acquired infections and bacterial pneumonia. EMA and FDA approvals for the use of telithromycin were withdrawn due to the ocurrence of severe side effects, particularly hepatotoxocity. It appears to still be authorised in some countries.
External links Click here for help