基本情報
- CAS
19388-87-5- 標準SMILES
O=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN1- InChIKey
AJKIRUJIDFJUKJ-UHFFFAOYSA-N- 分子式
- C7H16N4O4S2
- 平均分子量
- 284.4 g/mol
- 単同位体質量
- 284.06129735
概要
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.
名称と識別子
- 優先名称
- Taurolidine
- IUPAC
- 4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide
- 現地名
- タウロリジン
- 英語名
- Taurolidine
- 分子式
- C7H16N4O4S2
- 分子量
- 284.36
名称と別名
TAUROLIDINE19388-87-5TaurolinTaurolineTaurolidinaTaurolidinumCyclo-taurolidine4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide(cyclo)-taurolidine8OBZ1M4V3VW-3100MDTXSID00173001
名称をさらに表示
タウロリジン4,4'-メチレンビス(テトラヒドロ-2H-1,2,4-チアジアジン1,1-ジオキシド)タウロリン4,4′-メチレンビス(テトラヒドロ-2H-1,2,4-チアジアジン1,1-ジオキシド)4-[(1,1-ジオキシド-1,2,4-チアジアジナン-1,1-ジイウム-4-イル)メチル]-1,2,4-チアジアジナン-1,1-ジイウム-1,1-ビス(オラート)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
物性
構造計算による物性
- XLogP
- -1.7
- 極性表面積
- 116 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 8
- 回転可能結合数
- 2
- 重原子数
- 17
- 形式電荷
- 0
- 複雑度
- 419
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 154 · 154-158°
- 沸点
- 471.2 · 471.2±55.0 °C(Predicted)
- 比重(密度)
- 1.466 · 1.466±0.06 g/cm3(Predicted)
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- 20 mg/mL · DMSO：>20mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 11.16 · 11.16±0.20(Predicted)
- 色
- ホワイトからオフホワイト
- 安定性
- 水溶液中で不安定
- 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
- SMILES
- O=S1(=O)CCN(CN1)CN2CCS(=O)(=O)NC2
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
安全データ
- wgk
- 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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.
用途と製造
UsesUse (kg; approx.) in Germany (2009): >50
応用分野
使用Taurolidine 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.
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