taurolidine   Click here for help

GtoPdb Ligand ID: 13030

Synonyms: Defencath® (taurolidine + heparin) | taurolin
Approved drug
taurolidine is an approved drug (FDA (2023))
Compound class: Synthetic organic
Comment: Taurolidine is a thiadiazinane antimicrobial compound used to reduce the incidence of catheter-related bloodstream infections [1].

taurolidine 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 8
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 115.58
Molecular weight 284.36
XLogP -1.81
No. Lipinski's rules broken 0

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 C1CS(=O)(=O)NCN1CN2CCS(=O)(=O)NC2
Isomeric SMILES C1CS(=O)(=O)NCN1CN2CCS(=O)(=O)NC2
InChI InChI=1S/C7H16N4O4S2/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11/h8-9H,1-7H2
InChI Key AJKIRUJIDFJUKJ-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2023)
IUPAC Name Click here for help
4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide
International Nonproprietary Names Click here for help
INN number INN
2885 taurolidine
Synonyms Click here for help
Defencath® (taurolidine + heparin) | taurolin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Taurolidine
Other databases
CAS Registry No. 19388-87-5 (source: Scifinder)
ChEBI CHEBI:135173
ChEMBL Ligand CHEMBL2105420
DrugBank Ligand DB12473
DrugCentral Ligand 2568
GtoPdb PubChem SID 485206151
PubChem CID 29566
Search Google for chemical match using the InChIKey AJKIRUJIDFJUKJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AJKIRUJIDFJUKJ
Search PubMed clinical trials taurolidine
Search PubMed titles taurolidine
Search PubMed titles/abstracts taurolidine
UniChem Compound Search for chemical match using the InChIKey AJKIRUJIDFJUKJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AJKIRUJIDFJUKJ-UHFFFAOYSA-N
Wikipedia Taurolidine

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MedChemExpress
Taurolidine (links to external site)
Cat. No. HY-W011522