Taurultam - CAS 38668-01-8
Catalog number: B0084-114907
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C3H8N2O2S
Molecular Weight:
136.169
COA:
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Targets:
Others
Description:
Taurultam is a compound with antibacterial activity. It has shown inhibitory effect on cell proliferation and cell adhesion in angiogenesis.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-114907 100 mg $198 In stock
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Purity:
>95%
Appearance:
White Solid
Synonyms:
1,2,4-Thiadiazinane 1,1-dioxide
MSDS:
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Boiling Point:
273.8±50.0 °C at 760 mmHg
Melting Point:
140-142°C
Density:
1.3±0.1 g/cm3
InChIKey:
RJGYJMFQWGPBGM-UHFFFAOYSA-N
InChI:
InChI=1S/C3H8N2O2S/c6-8(7)2-1-4-3-5-8/h4-5H,1-3H2
Canonical SMILES:
C1CS(=O)(=O)NCN1
1.Taurolidine and congeners activate hTRPA1 but not hTRPV1 channels and stimulate CGRP release from mouse tracheal sensory nerves.
Kichko TI1, Pfirrmann RW2, Reeh PW1. Pharmacol Res Perspect. 2016 Feb 1;4(1):e00204. doi: 10.1002/prp2.204. eCollection 2016.
Taurolidine has long been in clinical use as an antimicrobial irrigation that does not impede wound healing. It can even be administered intravenously (30 g/day) to treat sepsis or to exert newly recognized antineoplastic actions. Only one irritant effect is reported, that is, to temporarily induce burning pain of unknown origin when applied to body cavities or peripheral veins. The structure of the molecule suggested the chemoreceptor channel TRPA1 as a potential target, which was verified measuring stimulated CGRP release from sensory nerves of the isolated mouse trachea and calcium influx in hTRPA1-transfected HEK293 cells. With both methods, the concentration-response relationship of taurolidine exceeded the threshold value below 500 μmol/L and 100 μmol/L, respectively, and reached saturation at 1 mmol/L. The clinical 2% taurolidine solution did not evoke greater or longer lasting responses. The reversible tracheal response was abolished in TRPA1(-/-) but retained in TRPV1(-/-) mice.
2.The pharmacokinetics of taurolidine metabolites in healthy volunteers.
Gong L1, Greenberg HE, Perhach JL, Waldman SA, Kraft WK. J Clin Pharmacol. 2007 Jun;47(6):697-703. Epub 2007 Mar 29.
Taurolidine is an experimental antibacterial and antiendotoxic compound whose clinical utility as an antitumor agent is being investigated in human clinical trials. Taurolidine in aqueous solution exists in equilibrium with taurultam. Taurultam is subsequently transformed to taurinamide. The pharmacokinetic profiles of these metabolites are not well established. In this study, 18 healthy volunteers were administered 5.0 g of taurolidine in 250 mL of 5% polyvinylpyrrolidone in water over 2, 1, or 0.5 hours by intravenous infusion in a parallel-group design. All subjects noted discomfort at the infusion site, although there were no serious adverse events. t(max) generally occurred at the end of infusion for taurinamide, whereas that of taurultam was reached before completion of infusion. The taurolidine metabolite taurultam demonstrated a shorter half-life and lower systemic exposure than taurinamide. Shortening of infusion duration increased the C(max) and AUC of taurultam.
3.Studies of the thiadiazine, taurolidine-I. Identification of the molecular species present in aqueous solutions by (1)H- and (13)C-NMR spectroscopy.
Hood HT1, Smail GA, Skellern GG, Jindal DP, Browne MK, Pfirrmann RW. Talanta. 1994 Jan;41(1):107-13.
The equilibria in deuterium oxide solutions of the diamine, 4,4'-methylenebis(tetrahydro-1,2,4-thiadiazine-1,1-dioxide), were studied using highfield (1)H- and (13)C-NMR with the aid of solutions of tetrahydro-2H-1,2,4-thiadiazine-1,1-dioxide (taurultam), its two N-methyl detivatives and methylene glycol. Comparison of the (1)H-NMR spectrum of taurolidine with the one obtained from a mixture of taurultam and methylene glycol indicated that the same equilibria exists in both these solutions. It was concluded that taurolidine, taurultam and its 4-hydroxymethyl adduct and methylene glycol are the major components present. To facilitate the interpretation of the (13)C-spectra, (13)C-enriched methylene glycol was added to solutions of taurultam. The (13)C-studies confirmed the (1)H-NMR study.
4.Structural investigation of a new organic antiseptic: Taurolidine A spectroscopic study of its stability and equilibria in various solvents.
Erb F1, Febvay N, Imbenotte M. Talanta. 1982 Nov;29(11 Pt 1):953-8.
(1)H and (13)C NMR investigations of aqueous solutions of Taurolidine and Tauroflex have been made to determine their stability. This study revealed two successive equilibria, leading particularly to Taurultam-methylol (in 15% proportion) from a 0.5% Taurolidine solution. The methylol derivative is supposed to be the component active against bacteria and their endotoxins.
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CAS 38668-01-8 Taurultam

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