Telithromycin

Telithromycin is the first ketolide antibiotic to enter clinical use and is sold under the brand name of Ketek. It is used to treat community acquired pneumonia of mild to moderate severity. After significant safety concerns, the US Food and Drug Administration sharply curtailed the approved uses of the drug in early 2007.

Telithromycin
Clinical data
Trade namesKetek, others
AHFS/Drugs.comMonograph
MedlinePlusa604026
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability57%
Protein binding66% to 79%
MetabolismHepatic (50% CYP3A4-mediated)
Elimination half-life10 hours
ExcretionBiliary and renal
Identifiers
  • (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2S,3R,4S,6R)-
    4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-
    2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-
    [4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-
    azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.208.206
Chemical and physical data
FormulaC43H65N5O10
Molar mass812.018 g·mol−1
3D model (JSmol)
Melting point177 °C (351 °F)
  • O=C2[C@@H]([C@@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@@](OC)(C)C[C@H](C(=O)[C@H](C)[C@H]3N(C(=O)O[C@]3(C)[C@H](OC(=O)[C@@H]2C)CC)CCCCn4cc(nc4)c5cccnc5)C)C
  • 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 Y
  • Key:LJVAJPDWBABPEJ-PNUFFHFMSA-N Y
 NY (what is this?)  (verify)

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 oxygen at the 6 position is methylated, as is the case with clarithromycin, to achieve better acid-stability.

It was patented in 1994 and approved for medical use in 2001.

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