telithromycin   Click here for help

GtoPdb Ligand ID: 10878

Synonyms: HMR-3647 | Ketek® | Levviax® | RU-66647 | RU66647
Approved drug
telithromycin is an approved drug (EMA (2001), FDA (2004))
Compound class: Synthetic organic
Comment: Telithromycin is a ketolide antibiotic [1-2,4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 171.85
Molecular weight 811.47
XLogP 3.03
No. Lipinski's rules broken 2
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Canonical SMILES CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]2[C@]1(C)OC(=O)N2CCCCn1cnc(c1)c1cccnc1)C)C)(C)OC
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]2[C@]1(C)OC(=O)N2CCCCn1cnc(c1)c1cccnc1)C)C)(C)OC
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
1. Edlund C, Sillerström E, Wahlund E, Nord CE. (1998)
In vitro activity of HMR 3647 against anaerobic bacteria.
J Chemother, 10 (4): 280-4. [PMID:9720465]
2. Goldstein EJ, Citron DM, Hunt Gerardo S, Hudspeth M, Merriam CV. (1998)
Activities of HMR 3004 (RU 64004) and HMR 3647 (RU 66647) compared to those of erythromycin, azithromycin, clarithromycin, roxithromycin, and eight other antimicrobial agents against unusual aerobic and anaerobic human and animal bite pathogens isolated from skin and soft tissue infections in humans.
Antimicrob Agents Chemother, 42 (5): 1127-32. [PMID:9593139]
3. Makgatho M, Maimela E, Mbajiorgu F. (2015)
Ketolide agents HMR 3004 and HMR 3647 (telithromycin) inhibit the growth of Plasmodium falciparum in vitro.
Afr Health Sci, 15 (4): 1271-6. [PMID:26958030]
4. Malathum K, Coque TM, Singh KV, Murray BE. (1999)
In vitro activities of two ketolides, HMR 3647 and HMR 3004, against gram-positive bacteria.
Antimicrob Agents Chemother, 43 (4): 930-6. [PMID:10103202]