tulathromycin   Click here for help

GtoPdb Ligand ID: 13691

Synonyms: Draxxin® (veterinary) | tulathromycin A
Compound class: Synthetic organic
Comment: Tulathromycin is a macrolide (triamilide subclass) antibacterial that was developed for use in veterinary medicine [3]. It consists of an equilibrated mixture of a 15-membered and a 13-membered ring component in a 9:1 ratio [2]. We show the structure for tulathromycin A, the 15-membered isomer.
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 15
Hydrogen bond donors 7
Rotatable bonds 11
Topological polar surface area 200.9
Molecular weight 806.08
XLogP 2.47
No. Lipinski's rules broken 4

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 CCCNC[C@@]1([C@H](C)O[C@H](C[C@@]1(C)OC)O[C@H]2[C@H](C)[C@H]([C@@](C)(C[C@@H](C)CN[C@H](C)[C@H]([C@@](C)([C@@H](CC)OC(=O)[C@@H]2C)O)O)O)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O
Isomeric SMILES CCCNC[C@@]1([C@@H](O[C@H](C[C@@]1(C)OC)O[C@H]2[C@@H]([C@H]([C@](C[C@H](CN[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]2C)CC)(C)O)O)C)C)(C)O)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)C)C)O
InChI InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1
InChI Key GUARTUJKFNAVIK-QPTWMBCESA-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
Tulathromycin is administered by subcutaneous or intramuscular injection. It has been licensed for veterinary use by the European Medicines Agency (EMA) since 2003 and is indicated for the control and treatment of bovine respiratory disease (BRD), the treatment of infectious bovine keratoconjunctivitis, the treatment of swine respiratory disease (SRD), and the systemic treatment of infectious pododermatitis (foot rot) in sheep. In 2005, tulathromycin was approved by the US FDA for the control and treatment of BRD and SRD.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The macrolide class of antibacterials inhibit protein synthesis by blocking function of the bacterial 50S ribosomal subunit. Tulathromycin binds to the same site on the ribosome as erythromycin and is not active against erythromycin-resistant ribosomes [4].