NAV

Taurolidine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Taurolidine is an antimicrobial derivative of taurine used for prophylaxis of catheter-related infections.

Brand Names
Defencath
Generic Name
Taurolidine
DrugBank Accession Number
DB12473
Background

Taurolidine is an antimicrobial used for the prevention of catheter-related infections. It is a derivative of the amino acid taurine.

It was first synthesized in the 1970s and was originally used as a prophylactic against intraperitoneal bacterial infections in patients with peritonitis.3 In November 2023, a catheter lock solution of taurolidine in combination with heparin - marketed as Defencath - received FDA approval under the Limited Population Pathway for Antibacterial and Antifungal Drugs (LPAD pathway) for the prevention of catheter-related bloodstream infections in a limited and specific patient population.6

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 284.35
Monoisotopic: 284.061297359
Chemical Formula
C7H16N4O4S2
Synonyms
  • Taurolidine
External IDs
  • W-3100M
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Pharmacology

Indication

Taurolidine is indicated in combination with heparin to reduce the incidence of catheter-related bloodstream infections (CRBSI) in adult patients with kidney failure receiving chronic hemodialysis (HD) through a central venous catheter (CVC).4

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for prophylaxis ofCatheter-related bloodstream infectionCombination Product in combination with: Heparin (DB01109)••••••••••••••••••••••• •••••••••••••••
Prophylaxis ofInfection••••••••••••••••••••
Prophylaxis ofInfection••••••••••••••••••••
Prophylaxis ofSoft tissues infections••••••••••••••••••••
Prophylaxis ofTissue adhesions••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Taurolidine is a broad-spectrum antimicrobial with activity against both Gram-positive and Gram-negative bacteria, in addition to mycobacteria and certain strains of fungi.5 The mechanism of action of taurolidine and its active metabolites is non-specific and involves the irreversible binding of its methylol groups to microbial cell walls, resulting in a subsequent loss of cell wall integrity and eventual cell death.4,5,3 In addition, it appears to reduce bacterial adhesion to mammalian cells and neutralize bacterial endo- and exotoxins.5,3

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

In an aqueous solution, taurolidine exists in an equilibrium with taurultam, which is subsequently metabolized to taurinamide.3 Both taurultam and taurinamide contribute to the antimicrobial activity of taurolidine.

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Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Taurolidine is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Taurolidine is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Taurolidine is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Taurolidine is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Taurolidine is combined with Bupivacaine.
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DefencathTaurolidine (67.5 mg/5mL) + Heparin (5000 [USP'U]/5mL)SolutionIntraluminalCorMedix Inc.2024-04-092024-04-09US flag
DefencathTaurolidine (40.5 mg/3mL) + Heparin (3000 [USP'U]/3mL)SolutionIntraluminalCorMedix Inc.2024-04-09Not applicableUS flag

Categories

ATC Codes
B05CA05 — Taurolidine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as thiadiazinanes. These are organic heterocyclic compounds containing a six-membered saturated heterocycle with two nitrogen, one sulfur, and three carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiadiazinanes
Sub Class
Not Available
Direct Parent
Thiadiazinanes
Alternative Parents
Organosulfonamides / Organic sulfonamides / Azacyclic compounds / Aminals / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic heteromonocyclic compound / Aminal / Azacycle / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic sulfonic acid amide / Organic sulfonic acid or derivatives / Organonitrogen compound
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Fungi
  • Mycobacteria
  • Bacteria

Chemical Identifiers

UNII
8OBZ1M4V3V
CAS number
19388-87-5
InChI Key
AJKIRUJIDFJUKJ-UHFFFAOYSA-N
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
IUPAC Name
4-[(1,1-dioxo-1lambda6,2,4-thiadiazinan-4-yl)methyl]-1lambda6,2,4-thiadiazinane-1,1-dione
SMILES
O=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN1

References

Synthesis Reference

Manik Reddy Pullagurla, Jagadeesh Babu Rangisetty, Neelam Naidu Dokula, "Process for the preparation of taurolidine and its intermediates thereof" European Patent EP2643308A1, filed November 2011.

General References
  1. van den Bosch CH, Jeremiasse B, van der Bruggen JT, Frakking FNJ, Loeffen YGT, van de Ven CP, van der Steeg AFW, Fiocco MF, van de Wetering MD, Wijnen MHWA: The efficacy of taurolidine containing lock solutions for the prevention of central-venous-catheter-related bloodstream infections: a systematic review and meta-analysis. J Hosp Infect. 2022 May;123:143-155. doi: 10.1016/j.jhin.2021.10.022. Epub 2021 Nov 9. [Article]
  2. Wouters Y, Mennen GRH, Te Morsche RHM, Roelofs HMJ, Wanten GJA: The Antiseptic and Antineoplastic Agent Taurolidine Modulates Key Leukocyte Functions. In Vivo. 2022 Sep-Oct;36(5):2074-2082. doi: 10.21873/invivo.12933. [Article]
  3. Gong L, Greenberg HE, Perhach JL, Waldman SA, Kraft WK: The pharmacokinetics of taurolidine metabolites in healthy volunteers. J Clin Pharmacol. 2007 Jun;47(6):697-703. doi: 10.1177/0091270007299929. Epub 2007 Mar 29. [Article]
  4. FDA Approved Drug Products: Defencath (taurolidine and heparin) catheter lock solution for central venous catheter instillation use [Link]
  5. CorMedix: About DefenCath [Link]
  6. FDA News & Events for Human Drugs: FDA approves new drug under special pathway for patients receiving hemodialysis [Link]
  7. Cayman Chemical: Taurolidine MSDS [Link]
Human Metabolome Database
HMDB0258744
PubChem Compound
29566
PubChem Substance
347828711
ChemSpider
27486
RxNav
2670453
ChEBI
135173
ChEMBL
CHEMBL2105420
ZINC
ZINC000019322537
Wikipedia
Taurolidine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionCentral Venous Catheterization / Parenteral Nutrition, Home1
4Unknown StatusPreventionCatheter Related Infections1
4Unknown StatusPreventionHemodialysis Catheter Infection / Thrombosis; Dialysis Catheter1
3CompletedPreventionCatheter Related Infections / Renal Failure, Chronic Renal Failure1
3CompletedPreventionInfection / Parenteral Nutrition / Sepsis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionIntraluminal
SolutionIntraperitoneal0.5 %
SolutionIntraperitoneal2 %
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8541393No2004-11-022024-11-02US flag
US7696182No2005-05-162025-05-16US flag
US11738120No2022-04-152042-04-15US flag
US9339036No2004-11-022024-11-02US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility16.2 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.5Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.53Chemaxon
pKa (Strongest Basic)1.97Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area98.82 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity60.73 m3·mol-1Chemaxon
Polarizability26.08 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a6u-8940000000-7b75be2f3e66c75e7051
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-ab37ea2e1ae4d678c3d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-7c8481c515ead68db54c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-1980000000-e1691a260b9312a0b927
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0015-1930000000-314b0a5beec0eda25903
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002g-0920000000-0387eb1414fff14489a7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-af86ff7fba120f58faf4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-167.3272884
predicted
DarkChem Lite v0.1.0
[M-H]-146.82414
predicted
DeepCCS 1.0 (2019)
[M+H]+168.3239884
predicted
DarkChem Lite v0.1.0
[M+H]+149.21971
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.3412884
predicted
DarkChem Lite v0.1.0
[M+Na]+155.25665
predicted
DeepCCS 1.0 (2019)

Drug created at October 20, 2016 22:31 / Updated at February 17, 2024 08:26