Compound ID | 1997

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Modithromycin

Synonym(s): EDP-420  |  EP-013420  |  S-013420

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, 6,11-bridged bicyclolide
Institute where first reported: Enanta, Shionogi & Co
Year first mentioned: 1981
Highest development stage: Phase 2 (NCT00270517)
Development status: Inactive
Reason dropped: Submission for this trial had been cancelled
Chemical structure(s):
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Molecular weight: 841
Iso. SMILES: CC[C@@H]1[C@@]([C@H]2[C@H](C(=NC(=O)C)[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)(OC/C(=N/OCC4=CN=C(C=C4)N5C=CC=N5)/CO2)C)C)C)(C)O
InChI Key: WLGSYOKBEDVHQB-ZIJNRMRWSA-N
Can. SMILES: CC[C@@H]1[C@](C)([C@H]2[C@@H](C)C(=NC(=O)C)[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/C(=N/OCC4=CC=C(N=C4)N5C=CC=N5)/CO2)O
InChI: InChI=1S/C43H64N6O11/c1-12-33-43(9,54)39-26(4)35(46-29(7)50)24(2)19-42(8,56-23-31(22-55-39)47-57-21-30-14-15-34(44-20-30)49-17-13-16-45-49)38(27(5)36(51)28(6)40(53)59-33)60-41-37(52)32(48(10)11)18-25(3)58-41/h13-17,20,24-28,32-33,37-39,41,52,54H,12,18-19,21-23H2,1-11H3/b46-35?,47-31+/t24-,25-,26+,27+,28-,32+,33-,37-,38-,39-,41+,42-,43-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9875927
Guide to Pharmacology: modithromycin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/25154307/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2715630/

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