Compound ID | 1996

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Telithromycin

Class: Macrolide (14-membered macrolide, ketolide)

Spectrum of activity: Gram-positive
Details of activity: Binds to the peptidyl transferase component of the 50S subunit of ribosomes, thus inhibiting peptide bond formation and bacterial protein synthesis. It is active against Gram-positive bacteria.
Description: Semisynthetic macrolide
Year first mentioned: 1994
Development status: Approved, withdrawn in most countries
Reason dropped: Reversible visual disturbance, syncope, exacerbation of myasthenia gravis and hepatic failure
Chemical structure(s):
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Molecular weight: 812.01
Iso. 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
InChI Key: LJVAJPDWBABPEJ-PNUFFHFMSA-N
Can. SMILES: CC[C@@H]1[C@]2(C)[C@@H]([C@@H](C)C(=O)[C@H](C)C[C@](C)([C@@H]([C@@H](C)C(=O)[C@@H](C)C(=O)O1)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)OC)N(CCCCN4C=C(C5=CN=CC=C5)N=C4)C(=O)O2
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3002190
Guide to Pharmacology: telithromycin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5509991/
  • https://www.scirp.org/journal/paperinformation.aspx?paperid=101981

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