spiramycin   Click here for help

GtoPdb Ligand ID: 13312

Synonyms: foromacidin | Rovamycine®
Approved drug PDB Ligand
spiramycin is an approved drug
Compound class: Natural product
Comment: Spiramycin is a 16-membered macrolide antimicrobial, produced by Streptomyces ambofaciens and originally isolated from soil samples [3].

spiramycin is commercially available from our sponsors

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 16
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 195.38
Molecular weight 843.05
XLogP 1.93
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 C[C@@H]1C[C@H](CC=O)[C@@H]([C@H]([C@@H](CC(=O)O[C@H](C)C/C=C/C=C/[C@@H]1O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O[C@H]4C[C@](C)([C@H]([C@H](C)O4)O)O)N(C)C)O
Isomeric SMILES C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)OC)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)O)(C)O)N(C)C)O)CC=O)C)O[C@H]4CC[C@@H]([C@H](O4)C)N(C)C
InChI InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1
InChI Key ACTOXUHEUCPTEW-CEUOBAOPSA-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
There is no information regarding current approval for clinical use of this drug on the US FDA or European Medicines Agency (EMA) websites. However, individual European agencies have authorised its use and it may be available in other jurisdictions.
Spiramycin can be administered orally or parenterally and used to treat a wide range of bacterial infections. A combination of spiramycin + metronidazole is used for the treatment and prevention of periodontal infections. Spiramycin is also used in the treatment of toxoplasmosis, an infection with the protozoan parasite Toxoplasma gondi that can cause serious complications during pregnancy and in patients with weakened immune systems.