Compound ID | 756

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HMR-3562

Synonym(s): HMR 3562  |  HMR3562

Class: Macrolide

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Active against pathogens causing respiratory tract infection including Haemophilus influenzae
Description: A 2-fluoroketolide derivative
Institute where first reported: Aventis (Sanofi-Aventis, France)
Year first mentioned: 1999
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Shows toxicity issues as a result of long QT
Chemical structure(s):
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Molecular weight: 830
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@](C(=O)O1)(C)F)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: RSIQCUSPSFSWMQ-XXTFOGKVSA-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@@](C)(C(=O)O1)F)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/C43H64FN5O10/c1-12-32-43(8)35(49(40(54)59-43)19-14-13-18-48-23-30(46-24-48)29-16-15-17-45-22-29)27(4)33(50)25(2)21-41(6,55-11)37(28(5)36(52)42(7,44)39(53)57-32)58-38-34(51)31(47(9)10)20-26(3)56-38/h15-17,22-28,31-32,34-35,37-38,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,31+,32-,34-,35-,37-,38+,41-,42+,43-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6918484
Citation: http://jac.oxfordjournals.org/content/48/1/131.full

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