Compound ID | 3264

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Tilmicosin

Synonym(s): EL-870  |  EL870  |  EL 870  |  Micotil

Class: Macrolide

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Protein synthesis inhibitor. Binds to peptidyl transferase centre to prevent translocation
Target Pathogen: Indicated for bovine and swine respiratory tract infections
Description: Semi-synthetic compound; derived from tylosin
Year first mentioned: 1987
Highest development stage: Approved for veterinary use in 1990
Development status: Experimental
Reason dropped: Injection into pigs reported to be fatal
Chemical structure(s):
Click here for structure editor
Molecular weight: 869.13
Iso. SMILES: CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)N(C)C)O)CCN3C[C@@H](C[C@@H](C3)C)C)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
InChI Key: JTSDBFGMPLKDCD-XVFHVFLVSA-N
Can. SMILES: CC[C@@H]1[C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@H](CCN2C[C@H](C)C[C@H](C)C2)[C@@H]([C@@H](C)[C@@H](CC(=O)O1)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O)N(C)C)O)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](C)O4)O)OC)OC
InChI: InChI=1S/C46H80N2O13/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3/b15-14+,25-19+/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,38+,39-,40-,41-,42-,43-,44-,45+,46-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5282521
Guide to Pharmacology: tilmicosin
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/42/8/42_8_1253/_article
  • https://www.jstage.jst.go.jp/article/antibiotics1968/40/2/40_2_190/_article

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