Compound ID | 2003

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Dirithromycin

Synonym(s): Dynabac  |  LY 237216

Class: Small molecule antibacterial agent

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to the peptidyl transferase component of the bacterial 50S ribosomal subunit, thus inhibiting peptide bond formation
Description: Semisynthetic erythromycin derivative
Institute where first reported: Lilly Research Labs
Year first mentioned: 1987
Highest development stage: Approved by FDA in 1995
Development status: Approved
Reason dropped: Discontinued/Withdrawn in US
Chemical structure(s):
Click here for structure editor
Molecular weight: 835.08
Iso. SMILES: CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O
InChI Key: WLOHNSSYAXHWNR-DWIOZXRMSA-N
Can. SMILES: CC[C@@H]1[C@](C)([C@H]2[C@@H](C)[C@H]([C@H](C)C[C@](C)([C@@H]([C@@H](C)[C@@H]([C@@H](C)C(=O)O1)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)O)OC)O[C@H]4[C@@H]([C@H](C[C@@H](C)O4)N(C)C)O)O)N[C@@H](COCCOC)O2)O
InChI: InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6473883
Guide to Pharmacology: dirithromycin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7266154/
  • https://www.scirp.org/journal/paperinformation.aspx?paperid=101981

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