tylvalosin   Click here for help

GtoPdb Ligand ID: 13706

Synonyms: acetylisovaleryltylosin | Aivlosin® (veterinary)
Compound class: Synthetic organic
Comment: Tylvalosin is a 16-membered macrolide antibacterial compound derived by biotransformation of tylosin by Streptomyces thermotolerans [1-2]. 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 20
Hydrogen bond donors 3
Rotatable bonds 19
Topological polar surface area 250.81
Molecular weight 1042.26
XLogP 3.17
No. Lipinski's rules broken 3

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](CC=O)[C@@H]([C@@H](C)[C@@H](CC(=O)O1)OC(=O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](C)O2)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)OC(=O)CC(C)C)O)N(C)C)O)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@@H](C)O4)O)OC)OC
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)OC(=O)C)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC
InChI InChI=1S/C53H87NO19/c1-16-38-36(26-65-52-49(64-15)48(63-14)44(60)31(7)67-52)22-28(4)17-18-37(57)29(5)23-35(19-20-55)46(30(6)39(69-34(10)56)24-41(59)70-38)73-51-45(61)43(54(12)13)47(32(8)68-51)72-42-25-53(11,62)50(33(9)66-42)71-40(58)21-27(2)3/h17-18,20,22,27,29-33,35-36,38-39,42-52,60-62H,16,19,21,23-26H2,1-15H3/b18-17+,28-22+/t29-,30+,31-,32-,33+,35+,36-,38-,39-,42+,43-,44-,45-,46-,47-,48-,49-,50+,51+,52-,53-/m1/s1
InChI Key KCJJINQANFZSAM-HZDSEHBESA-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
Tylvalosin is licensed for veterinary use by the US FDA and by the European Medicines Agency (EMA). It is administered orally as tylvalosin tartrate and indicated for the treatment and control of respiratory tract infections in poultry caused by Mycoplasma gallisepticum, swine enzootic pneumonia caused by Mycoplasma hyopneumoniae, porcine proliferative enteropathy caused by Lawsonia intracellularis and swine dysentery, caused by Brachyspira hyodysenteriae.
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.