4-[(1,1-dioxo-1λ6,2,4-thiadiazinan-4-yl)methyl]-1λ6,2,4-thiadiazinane-1,1-dione

• ChemBase ID: 129715
• Molecular Formular: C7H16N4O4S2
• Molecular Mass: 284.35634
• Monoisotopic Mass: 284.06129701
• SMILES: C1CS(=O)(=O)NCN1CN1CCS(=O)(=O)NC1
• Canonical SMILES: O=S1(=O)CCN(CN1)CN1CCS(=O)(=O)NC1
• 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
• InChIKey: AJKIRUJIDFJUKJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1,1-dioxo-1λ^6,2,4-thiadiazinan-4-yl)methyl]-1λ^6,2,4-thiadiazinane-1,1-dione
• IUPAC Traditional name: taurolidine
• Synonyms: Taurolidine; 4,4′-Methylenebis(tetrahydro-1,2,4-sulfadiazine 1,1-dioxide); Taurolin; Tauroline; Taurolidine; 4,4′-亚甲双[四氢-2H-1,2,4-噻二嗪]1,1,1′,1′-四氧化物; 4,4′-亚甲基双(四氢-1,2,4-磺胺嘧啶 1,1-二氧化物); 牛磺罗定; 滔罗林

Database IDs

• CAS Number: 19388-87-5
• EC Number: 243-016-5
• MDL Number: MFCD00865076
• PubChem SID: 162224004
• PubChem CID: 29566
• ATC CODE: B05CA05
• Unique Ingredient Identifier: 8OBZ1M4V3V
• Wikipedia Title: Taurolidine

CALCULATED PROPERTIES

• Acid pKa: 10.53159
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.465884
• LogD (pH = 7.4): -2.4660373
• Log P: -2.4657514
• Molar Refractivity: 60.7345 cm^3
• Polarizability: 26.051668 Å^3
• Polar Surface Area: 98.82 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: protect from light
• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: >97% (NMR)
• Empirical Formula (Hill Notation): C7H16N4O4S2

DETAILS

Sigma Aldrich - T7329

Biochem/physiol Actions
Taurolidine is a broad spectrum antibiotic with antineoplastic activity, which induces apoptosis and decreases tumor cell proliferation. Taurolidine has been used with TNF-related-apoptosis-inducing ligand (TRAIL) to characterize synergistic responses in many apoptosis related signaling-proteins. Tauroline is also being used as a tool to study the various mechanisms of apoptosis and necrosis.