(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate

• ChemBase编号: 105414
• 分子式: C16H25N3O7S
• 平均质量: 403.4506
• 单一同位素质量: 403.14132116
• SMILES: O=C(O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]2SC1(C)C.O.O.O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C.O.O.O
• InChI: InChI=1S/C16H19N3O4S.3H2O/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;;;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);3*1H2/t9-,10-,11+,14-;;;/m1.../s1
• InChIKey: RXDALBZNGVATNY-CWLIKTDRSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
• IUPAC传统名: ampicillin trihydrate
• 别名: 氨苄青霉素; 氨苄西林 三水合物; 氨苄西林; 氨苄西林 三水合物; D-(-)-α-Aminobenzylpenicillin; Aminobenzylpenicillin trihydrate; alpha-Aminobenzylpenicillin trihydrate; AMPICILLIN TRIHYDRATE; Ampicillin; Ampicillin trihydrate; (2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate

登记号

• CAS号: 7177-48-2
• EC号: 200-709-7
• MDL号: MFCD00072036
• Beilstein号: 5399534
• PubChem SID: 162092119; 24891059; 24890564; 24869717
• PubChem CID: 23565

理论计算性质

• Acid pKa: 3.2380536
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.0056438
• LogD (pH = 7.4): -2.2605202
• Log P: -2.0066502
• 摩尔折射率: 87.5235 cm^3
• 极化性: 34.874416 Å^3
• 极化表面积: 112.73 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 198-200 °C (dec.)(lit.); 198-200°C; 200-202 °C (dec.)
• 比旋光度: [α]20/D +250±10°, c = 0.5% in H2O

安全信息

• 保存条件: 2-8°C
• RTECS编号: XH8425000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 36/37/38-42/43; R:22
• 安全公开号: 22-26-36/37; S:36/37/39
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H317-H319-H334-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥96.0% (NT); 96.0-100.5% anhydrous basis (HPLC)
• 级别: VETRANAL™, analytical standard
• 成盐信息: 3 H2O
• 适用性: meets USP testing specifications
• 燃烧残渣: ≤0.05%
• Empirical Formula (Hill Notation): C16H19N3O4S · 3H2O

详细说明

MP Biomedicals - 02190147

Trihydrate Crystalline

Sigma Aldrich - A6140

Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Ampicillin Trihydrate is commonly used to select for ampicillin resistance in mutated and transformed cells.

Sigma Aldrich - 31591

Application
欧洲委员会 (EU) 2009 年 12 月 22 日第 37/2010 号关于动物源食品中药理学活性物质最大残留限量及其分类的条例。
Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 10045

Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Ampicillin Trihydrate is commonly used to select for ampicillin resistance in mutated and transformed cells. It is used in intracellular targeting of antibiotics on biodegradable polymeric carriers 1. Nanoparticle-bound ampicillin has been shown to be more effective than free ampicillin against Listeria monocytogenes in mouse peritoneal macrophages2. Ampicillin has been shown to cause Clostridium difficile-Associated ileocecitis in the hamster model3.

Sigma Aldrich - A1593

Application
Used to select for ampicillin resistance in mutated and transformed cells.
Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.