Taurolidine
Basic information
- CAS
19388-87-5- Standard SMILES
O=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN1- InChIKey
AJKIRUJIDFJUKJ-UHFFFAOYSA-N- Molecular formula
- C7H16N4O4S2
- Average molar mass
- 284.4 g/mol
- Monoisotopic mass
- 284.06129735
Overview
Taurolidine is a member of the class of thiadiazinanes that is 1,2,4-thiadiazinane 1,1-dioxide substituted by a (1,1-dioxido-1,2,4-thiadiazinan-4-yl)methyl group at position 4. It is a broad-spectrum antiseptic used as lock therapy solution in patients with long term central venous catheters for the prevention of catheter related bloodstream infections. It has a role as an antibacterial agent, an antineoplastic agent, an antifungal agent, an antiseptic drug and an anti-inflammatory agent. It is a sulfone and a thiadiazinane.
Names & identifiers
- Preferred name
- Taurolidine
- IUPAC
- 4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide
- English name
- Taurolidine
- Molecular formula
- C7H16N4O4S2
- Molecular weight
- 284.36
Names & synonyms
TAUROLIDINE19388-87-5TaurolinTaurolineTaurolidinaTaurolidinumCyclo-taurolidine4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide(cyclo)-taurolidine8OBZ1M4V3VW-3100MDTXSID00173001
Show more names
TaurolidinTauroLTaurolidine USP/EP/BPCAS19388-87-5 TaurolidineTaurolidine, 10 mM in DMSOBenzaldehyde,3,4-dichloro-3-hydroxy-4,4'-methylenebis(1,2,4-thiadiazinane1,1-dioxide)
DEFENCATH COMPONENT TAUROLIDINETAUROLOCK COMPONENT TAUROLIDINE4-((1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl)-1,2,4-thiadiazinane 1,1-dioxide4-((1,1-dioxo-1lambda6,2,4-thiadiazinan-4-yl)methyl)-1lambda6,2,4-thiadiazinane-1,1-dione4-[(1,1-dioxo-1lambda6,2,4-thiadiazinan-4-yl)methyl]-1lambda6,2,4-thiadiazinane-1,1-dioneRefChem:187532bis(1,1-dioxo-perhydro-1,2,4-thiadiazinyl-4)methaneDTXCID7095492
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- -1.7
- Topological polar surface area
- 116 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 419
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 154 · 154-158°
- Boiling point
- 471.2 · 471.2±55.0 °C(Predicted)
- Density
- 1.466 · 1.466±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 20 mg/mL · DMSO: >20mg/mL
- form
- powder
- pka
- 11.16 · 11.16±0.20(Predicted)
- color
- white to off-white
- Stability
- Unstable in Aqueous Solution
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Warning
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
B - Blood and blood forming organs
QB - Blood and blood forming organs
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. 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. In addition, it appears to reduce bacterial adhesion to mammalian cells and neutralize bacterial endo- and exotoxins.
Metabolism/MetabolitesIn an aqueous solution, taurolidine exists in an equilibrium with taurultam, which is subsequently metabolized to taurinamide. Both taurultam and taurinamide contribute to the antimicrobial activity of taurolidine.
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >50
Applications
UsesTaurolidine is a derivative of the amino acid Taurine (T007850). Taurolidine exhibits antiendotoxin and antimicrobial activity, and has also been shown to exhibit antitumour activity in vitro and in vivo. Taurolidine is used for the treatment of sepsis and is utilized in hospitals to prevent catheter-related bloodstream infections.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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