(R)-4-Aminoisoxazolidin-3-one D-环丝氨酸

CAS 68-41-7 MFCD00005353

化学结构图

68-41-7
SMILES: N[C@@H]1CONC1=O |&1:1|

化学属性

Mol. FormulaC3H6N2O2
Mol. Weight102.09
Density1.278
Melting Point147°C
SolubilitySoluble in water. Slightly soluble in methanol, propylene glycol.
TSCANo
Appearance 无色针状或叶状结晶或无定形粉末。熔点155-156℃(分解)。溶于水,微溶于甲醇、乙醇、丁醇、丙二醇,异丙醇和丙酮,难溶或不溶于甲苯、氯仿、乙醚、吡啶、苯和二硫化碳。 powder
Boiling Point191.38 °C at 760 mmHg

别名和识别编码

Chemical Name(R)-4-Aminoisoxazolidin-3-one
CAS Number68-41-7
Alfabeta NameCYCLOSERINE D-
MDL NumberMFCD00005353
Synonym D-Cycloserine {LY} D-Cycloserine {} {LY} D-Cycloserine {} {} {LY} D-Cycloserine {} {} {} {LY} D-Cycloserine {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} D-Cycloserine {} {} {} {} {} {} {} {} {} {}
EC Number200-688-4
Beilstein Registry Number80798
PubChem Substance ID87566215
Reaxys-RN80798
Merck Number2751
Chemical Name TranslationD-环丝氨酸
Wiswesser Line NotationT5OMVTJ DZ -D
LabNetwork Molecule IDLN00173123
Canonical SMILESO=C1[C@H](N)CON1
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分类

  • {SNA} A - K, Amino Acid Derivatives, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antimycobacterial, Bioactive Small Molecules, Biochemicals and Reagents, CI-CY, Cell Signaling and Neuroscience, Chemical Structure Class, Excitatory Amino Acids, Genetic Marker Selection, Interferes with Cell Wall Synthesis, Ion Channels, Ionotropic Glutamate Receptor Modulators, Ligand-Gated Ion Channels, Mechanism of Action,
  • {SNA} A - K,
  • {SNA} A - K, Amino Acid Derivatives, Antibacterial, Antibiotics, Antibiotics A to Z,
  • {SNA} A - K,

产品应用

  • 抑制细胞壁合成(D -丙氨酸肽键形成)。也防止了D-丙氨酸转换为L -丙氨酸。抑菌。

相关文献及参考

  • Merck: 14,2751 Beilstein: 27,IV,5549
  • Wlaz, P., et al., Influence of D-cycloserine on the anticonvulsant activity of phenytoin and carbamazepine against electroconvulsions in mice. Epilepsia 37 , 610-617, (1996) 摘要
  • Mary M. Torregrossa, Hayde Sanchez, et al., D-Cycloserine Reduces the Context Specificity of Pavlovian Extinction of Cocaine Cues through Actions in the Nucleus Accumbens. J. Neurosci. 30 , 10526-10533, (2010) 摘要
  • Pussinen, R., and Sirvio, J., Effects of D-cycloserine, a positive modulator of N-methyl-D-aspartate receptors, and ST 587, a putative α-1 adrenergic agonist, individually and in combination, on the non-delayed and delayed foraging behaviour of rats assessed in the radial arm maze. Org. Process Res. Dev. 13 , 171, (1999)
  • Merck 14 ,2751
  • Schneider, J.S., et al., Effects of the partial glycine agonist D-cycloserine on cognitive functioning in chronic low dose MPTP-treated monkeys. Brain Res. 860 , 190-194, (2000) 摘要
  • Watson, et al., D-Cycloserine acts as a partial agonist at the glycine modulatory site of the NMDA receptor expressed in Xenopus oocytes. Brain Res. 510 , 158-160, (1990) 摘要
  • Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972),
  • Merck: 14,2751

安全信息

Warnings IRRITANT
Signal word Warning
GHS Symbol
WGK Germany2
Safety Statements
Risk Statements
  • R5 Heating may cause an explosion 加热会引起爆炸
  • R20 Harmful by inhalation 吸入有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
RTECSNY2975000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Storage condition 2-8°C {LY} 2-8°C Air Sensitive {} {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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard Codes Xn
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >3 gm/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
REFERENCE :
   ANTCAO Antibiotics and Chemotherapy (Washington, DC).  (Washington, DC)
   V.1-12, 1951-62.  For publisher information, see CLMEA3.
   Volume(issue)/page/year: 6,360,1956

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 5290 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - ataxia
REFERENCE :
   ANTCAO Antibiotics and Chemotherapy (Washington, DC).  (Washington, DC)
   V.1-12, 1951-62.  For publisher information, see CLMEA3.
   Volume(issue)/page/year: 6,360,1956

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 64 mg/kg/4D-I
TOXIC EFFECTS :
   Behavioral - sleep
   Behavioral - altered sleep time (including change in righting reflex)

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1400 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YKYUA6 Yakkyoku.  Pharmacy.  (Nan

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ANTCAO Antibiotics and Chemotherapy (Washington, DC).  (Washington, DC)
   V.1-12, 1951-62.  For publisher information, see CLMEA3

其他信息

  • 二线抗结核药:D-环丝氨酸是一种由淡紫灰链霉菌(Streptomyces lavendulae)和兰花链霉菌(S.orchidaceus)产生或由化学合成的多肽类广谱抗生素。为白色结晶,吸湿性强,易溶于水,可溶于低级醇、丙酮与二氧六环,难溶于氯仿与石油醚; 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。 D-环丝氨酸的抗菌作用的机理是抑制细胞壁肽聚糖的生物合成,因它是D-丙氨酸的结构类似物,可与D-丙氨酸竞争性地抑制肽聚糖合成过程中的两个重要酶——丙氨酸消旋酶和D-丙氨酰-D-丙氨酸合成酶。其抗结核分枝杆菌 (Mycobacterium tuberculosis)的能力弱,仅为链霉素的1/10~1/20。优点为对该菌的耐药株有效,且不易对它产生耐药性。本品可与其他抗结核药合用以治疗由耐药性结核分枝杆菌所引起的结核病。 环丝氨酸是二线抗结核药物,能抑制结核杆菌生长,但作用相对一线药较弱,对结核病的疗效也较低,单用可产生耐药性,但耐药性比其他抗结核药发生缓慢,与其它抗结核药之间无交叉耐药性。其抗菌作用机制是抑制细菌细胞壁粘肽的合成,从而使细胞壁缺损。细菌细胞壁主要结构成分是胞壁粘肽,由N-乙酰葡萄糖胺(GNAc)和与五肽相连的N-乙酰胞壁酸(MNAc)重复交替联结而成。胞浆内粘肽前体的形成可被环丝氨酸所阻碍,环丝氨酸通过抑制D-丙氨酸的消旋酶和合成酶可阻碍N-乙酰胞壁酸五肽的形成。 以上信息由Chemicalbook的Andy编辑整理。
  • 比旋光度:111 ° (C=5, 2N NaOH)
  • Sigma Aldrich:68-41-7(sigmaaldrich)
  • 用途一:抗菌素类药。用于耐药性结核杆菌的感染。
  • 溶于水,微溶于甲醇,乙醇,丁醇,丙二醇,异丙醇和丙酮,难溶或不溶于甲苯,氯仿,乙醚,吡啶,苯和二硫化碳。
  • 敏感性:Air Sensitive
  • Acros Organics:D-环丝氨酸 D-Cycloserine, 98+%(68-41-7)
  • D-环丝氨酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 C1189 D-(+)-环丝氨酸 D-(+)-Cycloserine 5G 1450元 2011/04/16 C1189 D-(+)-环丝氨酸 D-(+)-Cycloserine 1G 432元 2010/05/25 A18000 D-环丝氨酸, 98+% D-Cycloserine, 98+% 5g 2772元
  • F:10-23
  • MSDS 信息:D-Cycloserine(68-41-7).msds
  • MOL 文件:68-41-7.mol
  • 上游原料:碳酸钙 --> 硝酸铵 --> 大豆油 --> 糊精 --> 放线菌 --> D-丙氨酸
  • Alfa Aesar
  • D-环丝氨酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C1189 D-(+)-环丝氨酸 D-(+)-Cycloserine 5G 1760元 2014/06/02 C1189 D-(+)-环丝氨酸 D-(+)-Cycloserine 1G 524元 2010/05/25 A18000 D-环丝氨酸, 98+% D-Cycloserine, 98+% 5g 2772元
  • TCI Shanghai:D-(+)-环丝氨酸 D-(+)-Cycloserine,>;98.0%(LC)(T)(68-41-7)
  • 方法一:环丝氨酸可用发酵法或直接合成法制备。发酵法产生菌是赖氏放线菌(Actinomyces laven-dulae),发酵培养基为糊精、葡萄糖、淀粉、黄豆饼粉、酵母粉、硫酸铵、硝酸铵、碳酸钙、氯化钠、硫酸镁和豆油等。合成法是将β-氨基氧丙氨酸乙酯二盐酸盐和氢氧化钾反应,即环合得到环丝氨酸。

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