เทลิโทรมัยซิน

Also known as HMR-3647, 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.

Chemical data

Formula: C43H65N5O10
Molecular weight: 812 g/mol
IUPAC name: (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-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
SMILES: CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=C4)C5=CN=CC=C5)C
InChIKey: LJVAJPDWBABPEJ-PNUFFHFMSA-N
XLogP: 4.2
Polar surface area: 172 Å²
H-bond donors: 1
H-bond acceptors: 13
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2001
Admin. routes: oral
Indications: infection, pneumonia, Otitis media, maxillary sinusitis

via ChEMBL · EBI

Research

1,019 papers

Telithromycin.Drugs · 2004
Telithromycin.Expert review of anti-infective therapy · 2004
[Telithromycin].Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia · 2004
Telithromycin.Drugs · 2001
Telithromycin.Annals of internal medicine · 2006

via PubMed

Wikidata facts

Subclass of: ketolides
Mass: 811.473
Has use: medication

Show 8 more facts

chemical formula: C₄₃H₆₅N₅O₁₀
canonical SMILES: CCC1C2(C(C(C(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=C4)C5=CN=CC=C5)C
isomeric SMILES: CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=C4)C5=CN=CC=C5)C
defined daily dose: 0.8
subject has role: antibiotic
native label: Telithromycinum
Commons category: Telithromycin
legal status (medicine): boxed warning

Sources (8)

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