Telithromycin

Telithromycin
Clinical data
Trade names	Ketek, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604026
License data	EU EMA: by INN;
Routes of; administration	Oral
ATC code	J01FA15 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx only;
Pharmacokinetic data
Bioavailability	57%
Protein binding	66% to 79%
Metabolism	Hepatic (50% CYP3A4-mediated)
Elimination half-life	10 hours
Excretion	Biliary and renal
Identifiers
	IUPAC name (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	191114-48-4 ;
PubChem CID	5462516;
DrugBank	DB00976 ;
ChemSpider	2273373 ;
UNII	KI8H7H19WL;
KEGG	D01078 ;
ChEBI	CHEBI:29688;
ChEMBL	ChEMBL1136 ;
CompTox Dashboard (EPA)	DTXSID3046455 ;
ECHA InfoCard	100.208.206
Chemical and physical data
Formula	C43H65N5O10
Molar mass	812.018 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	177 °C (351 °F)
	SMILES 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 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 ; Key:LJVAJPDWBABPEJ-PNUFFHFMSA-N ;
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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 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.^[2]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 499. ISBN 9783527607495.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[Fis2006-2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 499. ISBN 9783527607495.

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