tildipirosin   Click here for help

GtoPdb Ligand ID: 13689

Synonyms: Zuprevo® (veterinary)
Compound class: Synthetic organic
Comment: Tildipirosin is a 16-membered macrolide antibacterial compound derived from tylosin. It was developed for use in veterinary medicine.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 132.24
Molecular weight 734.02
XLogP 2.95
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC[C@@H]1[C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@H](CCN2CCCCC2)[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)CN4CCCCC4
Isomeric 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)CCN3CCCCC3)C)\C)CN4CCCCC4
InChI InChI=1S/C41H71N3O8/c1-8-35-32(26-44-20-13-10-14-21-44)23-27(2)15-16-33(45)28(3)24-31(17-22-43-18-11-9-12-19-43)40(29(4)34(46)25-36(47)51-35)52-41-39(49)37(42(6)7)38(48)30(5)50-41/h15-16,23,28-32,34-35,37-41,46,48-49H,8-14,17-22,24-26H2,1-7H3/b16-15+,27-23+/t28-,29+,30-,31+,32-,34-,35-,37+,38-,39-,40-,41+/m1/s1
InChI Key HNDXPZPJZGTJLJ-UEJFNEDBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Tildipirosin is administered by subcutaneous or intramuscular injection. It has been licensed for veterinary use by the European Medicines Agency (EMA) since 2011 and is indicated for the control and treatment of bovine respiratory disease (BRD) and of swine respiratory disease (SRD). In 2012, tildipirosin was approved by the US FDA for the control and treatment of BRD in beef and non-lactating dairy cattle.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
A study using a combination of chemical footprinting and structure modeling has shown that tildipirosin binds in the polypeptide exit tunnel adjacent to the peptidyl transferase centre (PTC) of the bacterial 50S ribosomal subunit, suggesting that it inhibits bacterial protein synthesis by interfering with prolongation of the nascent polypeptide chain [2].