Editing Telithromycin (section)

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470478754
| IUPAC_name = (1''S'',2''R'',5''R'',7''R'',8''R'',9''S'',11''R'',13''R'',14''R'')-8-[(2''S'',3''R'',4''S'',6''R'')-<br />4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-<br />2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-<br />[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-<br />azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
| image = Telithromycin.svg
<!--Clinical data-->
| tradename = Ketek, others
| Drugs.com = {{drugs.com|monograph|telithromycin}}
| MedlinePlus = a604026
| pregnancy_AU = 
| pregnancy_US = C
| pregnancy_category = 
| licence_EU = yes
| legal_AU = 
| legal_CA = 
| legal_UK = POM
| legal_US = Rx only
| legal_status =

| routes_of_administration = Oral
<!--Pharmacokinetic data-->
| bioavailability = 57%
| protein_bound = 66% to 79%
| metabolism = [[Liver|Hepatic]] (50% [[CYP3A4]]-mediated)
| elimination_half-life = 10 hours
| excretion = Biliary and [[Kidney|renal]]
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 191114-48-4
| ATC_prefix = J01
| ATC_suffix = FA15
| PubChem = 5462516
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank = DB00976
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2273373
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KI8H7H19WL
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D01078
| ChEBI = 29688
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1136
<!--Chemical data-->
  | C=43 | H=65 | N=5 | O=10
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LJVAJPDWBABPEJ-PNUFFHFMSA-N
| melting_point = 177
}}

'''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.

<!-- Society and culture -->
It was patented in 1994 and approved for medical use in 2001.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=499 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA499 |language=en}}</ref>