L-Cycloserine 环丝氨酸

CAS 339-72-0 MFCD00064324

化学结构图

339-72-0
SMILES: N[C@H]1CONC1=O

化学属性

Mol. FormulaC3H6N2O2
Mol. Weight102.09
Melting Point147°C
Density1.28
Refractive index1.48
SolubilitySoluble in water (25 mg/ml).
Boiling Point191.38 °C at 760 mmHg

别名和识别编码

Chemical Name(S)-4-Aminoisoxazolidin-3-one
Synonym L-Cycloserine {LY} L-Cycloserine {} {LY} L-Cycloserine {} {} {LY} L-Cycloserine {} {} {} {LY} L-Cycloserine {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} L-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00064324
PubChem Substance ID449215
Beilstein Registry Number0080799
CAS Number339-72-0
EC Number206-427-0
Chemical Name Translation环丝氨酸
Wiswesser Line NotationT5OMVTJ DZ -L
LabNetwork Molecule IDLN01377957
InChIInChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m0/s1
Canonical SMILESO=C1NOC[C@@H]1N
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分类

  • {SNA} A to C, Alanine hydroxymethyltransferase, D-, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Peptides and Proteins, Peptides for Cell Biology
  • {SNA} A to C, Alanine hydroxymethyltransferase, D-, Biochemicals and Reagents, Cell Signaling and Neuroscience, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Peptides and Proteins, Peptides for Cell Biology, 细胞生物学
  • {SNA} A to C, Alanine hydroxymethyltransferase, D-, Biochemicals and Reagents, Enzyme Inhibitors,
  • {SNA} A to C,

产品应用

  • An irreversible inhibitor of 3-ketodihydrosphingosine synthetase

相关文献及参考

  • 1. Cinati, J. Jr., et al., Cytotoxicity of L-cycloserine against human neuroblastoma and medulloblastoma cells is associated with the suppression of ganglioside expression Anticancer Res. 19 , 5349-5354, (1999) 摘要
  • Rath, G., et al., De novo ceramide synthesis is responsible for the anti-tumor properties of camptothecin and doxorubicin in follicular thyroid carcinoma. Int. J. Biochem. Cell Biol. 41 , 1165-72, (2009) 摘要
  • Beil. 27 ,IV,5550

安全信息

WGK Germany2
RTECSNY2976000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Hazard Codes Xn
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Safety Statements
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S38 In case of insufficient ventilation wear suitable respiratory equipment 通风不良时,佩带适当的呼吸器;
Risk Statements
  • R5 Heating may cause an explosion 加热会引起爆炸
  • R20 Harmful by inhalation 吸入有害
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2492 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NEPHBW Neuropharmacology.  (Pergamon Press Ltd., Headington Hill Hall,
   Oxford OX3 OBW, UK) V.9-    1970-  Volume(issue)/page/year: 25,411,1986

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NEPHBW Neuropharmacology.  (Pergamon Press Ltd., Headington Hill Hall,
   Oxford OX3 OBW, UK) V.9-    1970-  Volume(issue)/page/year: 25,411,1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1071 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NEPHBW Neuropharmacology.  (Pergamon Press Ltd., Headington Hill Hall,
   Oxford OX3 OBW, UK) V.9-    1970-  Volume(issue)/page/year: 25,411,1986

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 500 mg/kg
TOXIC EFFECTS :
   Details of toxi

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1889 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NEPHBW Neuropharmacology.  (Pergamon Press Ltd., Headington Hill Hall,
   Oxford OX3 OBW, UK) V.9-    1970-  Volume(issue)/page/year: 25,411,1986

Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H332 Harmful if inhaled 吸入有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P264+P265
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P317
  • P302+P352
  • P304+P340
  • P305+P351+P338
  • P317
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P332+P317
  • P337+P317
  • P362+P364
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....

其他信息

  • MOL 文件:339-72-0.mol
  • 制备方法:① 由放线菌经发酵、提炼及精制而成环丝氨酸。 ② 以丝氨酸甲酯的盐酸盐为原料,在五氯化磷的催化作用下,与三氯甲烷反应,脱羟基,再在氢氧化钠溶液中与羟胺反应,可制得环丝氨酸。
  • Sigma Aldrich:339-72-
  • Acros Organics:L-环丝氨酸 L-Cycloserine, 99%(339-72-0)
  • 二线抗结核药:环丝氨酸属二线抗结核药,为广谱抗菌药物,对许多革兰阳性菌和阴性菌有较弱的抗菌作用。对结核杆菌具有抑制作用,抗结核杆菌作用远比异烟肼、链霉素弱,其抗菌机理是干扰细菌细胞壁的合成,抗结核杆菌的浓度为5~20mg/L,与其他抗结核药无交叉耐药性,细菌对之不易产生耐药性。由于对神经系统的毒性较大,仅用于其他药物治疗无效的患者。 口服吸收迅速,口服3~4小时达血药浓度峰值。口服一次0.25g达峰值平均为4mg/L,重复用药,可达到较高峰值。血浆半衰期为10小时。吸收后分布于全身组织、体液,可扩散进入胎儿循环和脑脊液、腹水、乳汁中。大部分以原形经肾排泄,肾功能不全者易蓄积中毒,小量从粪便中排出。 环丝氨酸的毒副作用主要为神经系统毒性反应。用药过程中如出现严重的精神症状,应立即停药。 从链丝菌培养液中提取的为D型,人工合成者为DL型光学异构体,临床所用环丝氨酸以后者为主,主要用于治疗结核病,特别适用于对其他抗结核药耐药的结核杆菌感染,常与其他抗结核药如异烟肼、链霉素和对氨基水杨酸等联用,也用于大肠杆菌所引起的尿路感染等。 信息由ChemicalBook的Andy编辑。
  • 理化性质:白色或微红色晶体或粉末。有吸湿性。易潮解。味微酸。熔点155~156℃ (分解),比旋光度+115°(c=1,水,22℃)、+137° (c=5,2mol/1NaOH)。易溶于水,溶于乙醇,微溶于氯仿、乙醚,不溶于一般有机溶剂。在碱性溶液中较为稳定,在酸性与中性溶液中则迅速分解。 环丝氨酸的抗菌谱广,除结核杆菌外,对大多数革兰阳性与阴性细菌、立克次体以及某些原虫等也都有抑制作用,对链霉素、紫霉素、对氨基水杨酸、异烟肼、吡嗪酰胺等耐药的结核杆菌也有作用。环丝氨酸与异烟肼对结核杆菌H37RV有轻度的协同作用,与链霉素既无协同亦不显示拮抗作用。本品为抑菌剂,增加剂量或延长与细菌作用时间,也不出现杀菌作用。本品抗菌作用的机理是抑制细菌细胞壁的合成。 环丝氨酸主要用于结核病,为二线药物,成人口服剂量为每日500mg,儿童为每日10mg/kg,均两次分服。重症病人可在短期内,增加剂量到每日1g。为了确保疗效又不致引起不良反应,在服药期间应定期测定血药浓度,以不超过30μg/ml为宜。同时服用巴比妥类药物,可减轻或防止惊厥发作。
  • F:10
  • L-Cycloserine is an irreversible inhibitor of 3-ketodihydrosphingosine synthetase, which is the first enzyme of the sphingolipid pathway, and causes the synthesis of sphingolipids to decrease. In vitro studies demonstrated that L-cyloserine inhibits 3-ketodihydrosphingosine synthetase 100 times more than D-Cycloserine .Research regarding L-Cycloserine and its effect on the immune response suggest that L-Cycloserine increases the level of IL-4 producing helper T cells and suppress the adhesion molecules CD29 and CD98. L-Cycloserine also inhibits SPTLC (serine palmitoyltransferase (SPT)), and HIV-1 investigations in the CD4+ lymphoid cell line (CEM) have shown that L-Cycloserine can inhibit HIV-1 replication.

系列性分类


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