CAS 339-72-0 MFCD00064324-L-Cycloserine 环丝氨酸 TAO{mole}

L-Cycloserine 环丝氨酸

CAS 339-72-0 MFCD00064324

化学结构图

SMILES: N[C@H]1CONC1=O

化学属性

Mol. Formula	C3H6N2O2
Mol. Weight	102.09
Melting Point	147°C
Density	1.28
Refractive index	1.48
Solubility	Soluble in water (25 mg/ml).
Boiling Point	191.38 °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 Number	MFCD00064324
PubChem Substance ID	449215
Beilstein Registry Number	0080799
CAS Number	339-72-0
EC Number	206-427-0
Chemical Name Translation	环丝氨酸
Wiswesser Line Notation	T5OMVTJ DZ -L
LabNetwork Molecule ID	LN01377957
InChI	InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m0/s1
Canonical SMILES	O=C1NOC[C@@H]1N

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产品应用

An irreversible inhibitor of 3-ketodihydrosphingosine synthetase

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.