4-amino-1,2-oxazolidin-3-one

• ChemBase编号: 145
• 分子式: C3H6N2O2
• 平均质量: 102.09194
• 单一同位素质量: 102.04292744
• SMILES: O1NC(=O)C(N)C1
• Canonical SMILES: NC1CONC1=O
• InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)
• InChIKey: DYDCUQKUCUHJBH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-1,2-oxazolidin-3-one
• IUPAC传统名: DL-cycloserine; (+-)-4-amino-3-isoxazolidinone
• 商标名: Closerin; Closina; Cyclomycin; Cyclorin; Cycloserin; Farmiserina; Farmiserine; Micoserina; Miroserina; Miroseryn; Novoserin; Orientomycin; Oxamicina; Oxamycin; Oxymycin; Seromycin; Tebemicina; Tisomycin; Wasserina
• 别名: 4-氨基-3-异噁唑烷酮; DL-环丝氨酸; D-环丝氨酸; 4-Amino-3-isoxazolidone; DL-Cycloserine; 4-Amino-3-isoxazolidinone; (R)-(+)-4-Amino-3-isoxazolidinone; D-Cycloserine; D-Cycloserine; (+/-)-3-Oxoisooxazolidin-4-amine; rac Cycloserine; 4-amino-1,2-oxazolidin-3-one; 4-Aminoisoxazolidin-3-one; alpha-Cycloserine; Cicloserina; D-CS; D-Cycloserine; D-Cycloserine synth. BP 88; D-Cycloserine, synthetic; D-Oxamicina; D-Oxamycin; DL-Cycloserine; L-Cycloserine; Cycloserine

登记号

• CAS号: 68-39-3; 68-41-7
• EC号: 200-688-4; 200-687-9
• MDL号: MFCD00005353; MFCD00064323
• Beilstein号: 80798
• 默克索引号: 142751
• PubChem SID: 24278332; 160963608
• PubChem CID: 401

理论计算性质

JChem

• Acid pKa: 4.210087
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -2.4357781
• LogD (pH = 7.4): -2.4206417
• Log P: -2.4213324
• 摩尔折射率: 21.8488 cm^3
• 极化性: 9.062646 Å^3
• 极化表面积: 64.35 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.31
• LOG S: 0.93
• 溶解度: 8.77e+02 g/l

分子性质

理化性质

• 溶解度: Soluble; Soluble in water. Slightly soluble in methanol, propylene glycol.; Water
• 外观: crystalline; Off-White Solid
• 熔点: >183°C (dec.); 137°C dec.
• 比旋光度: +115 (c=2 in water)
• 疏水性(logP): -0.9; -1.192

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Air Sensitive
• RTECS编号: NY2974900; NY2975000
• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... GPT(2875), GPT2(84706)

产品相关信息

• 纯度: 95%; 95+%; 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C3H6N2O2

详细说明

DrugBank - DB00260

• Drug Groups: approved
• Description: Antibiotic substance produced by Streptomyces garyphalus. [PubChem]
• Indication: Used in combination with up to 5 other drugs as a treatment for Mycobacterium avium complex (MAC) and is also used to treat tuberculosis (TB).
• Pharmacology: Cycloserine, a broad-spectrum antibiotic, may be bactericidal or bacteriostatic, depending on its concentration at the site of infection and the susceptibility of the organism. Cycloserine works by blocking the formation of these peptidoglycans. By doing this the walls of the bacteria become weak and it results in the death of the bacteria
• Toxicity: Oral LD₅₀ in mouse is 5290 mg/kg, and in rat is over 5000 mg/kg. Symptoms of a cycloserine overdose include drowsiness, confusion, headache, dizziness, irritability, numbness and tingling, difficulty speaking, paralysis, abnormal behavior, seizures, and unconsciousness.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Rapidly and almost completely absorbed (70 to 90%) from the gastrointestinal tract following oral administration.
• Half Life: Half-life in patients with normal renal function is 10 hours, and is prolonged in patients with impaired renal function.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - C7005

Biochem/physiol Actions
Inhibitor of alanine aminotransferase and other pyridoxal-phosphate-requiring transaminases1; blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase.

Sigma Aldrich - 862002

Biochem/physiol Actions
Inhibitor of alanine aminotransferase and other pyridoxal-phosphate-requiring transaminases1; blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase.

Toronto Research Chemicals - C988800

Antibacterial (tuberculostatic).

参考文献

• Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972)
• Gentry-Weeks, C., et al.: J. Biol. Chem., 268, 7298 (1972)
• Alexander, F., et al.: Eur. J. Biochem., 219, 953 (1972)
• Auger, S., et al.: Biochimie, 87, 231 (1972)