gamithromycin   Click here for help

GtoPdb Ligand ID: 13688

Synonyms: ML-1709460 | Zactran® (veterinary)
Compound class: Synthetic organic
Comment: Gamithromycin is a 15-membered macrolide (azalide subclass) antibacterial compound. 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 14
Hydrogen bond donors 5
Rotatable bonds 9
Topological polar surface area 180.08
Molecular weight 777.04
XLogP 2.67
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 CCCN1C[C@H](C)[C@H]([C@@](C)([C@@H](CC)OC(=O)[C@H](C)[C@H]([C@H](C)[C@H]([C@@](C)(C[C@H]1C)O)O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)O)OC)O)O
Isomeric SMILES CCCN1C[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H]1C)(C)O)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)CC)(C)O)O)C
InChI InChI=1S/C40H76N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h22-35,37,43-45,47-48H,15-21H2,1-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1
InChI Key VWAMTBXLZPEDQO-UZSBJOJWSA-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
Gamithromycin is administered by subcutaneous or intramuscular injection. It has been licensed for veterinary use by the European Medicines Agency (EMA) since 2008 and is indicated for the control and treatment of bovine respiratory disease (BRD), the treatment of swine respiratory disease (SRD) and the systemic treatment of infectious pododermatitis (foot rot) in sheep. In 2011, gamithromycin was approved by the US FDA for the control and treatment of BRD in beef and non-lactating dairy cattle.