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

• ChemBase ID: 105415
• Molecular Formular: C16H18N3NaO4S
• Molecular Mass: 371.38659
• Monoisotopic Mass: 371.09157135
• SMILES: [Na+].CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=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.[Na+]
• InChI: InChI=1S/C16H19N3O4S.Na/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);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1
• InChIKey: KLOHDWPABZXLGI-YWUHCJSESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium ampicillin(1-)
• Synonyms: D-(-)-α-Aminobenzylpenicillin sodium salt; Ampicillin sodium salt; AMINOBENZYLPENICILLIN SODIUM SALT; AMPICILLIN SODIUM SALT; AMPICILLIN SODIUM SALT γ-IRRADIATED; 氨苄青霉素 钠盐; 氨苄西林 钠盐

Database IDs

• CAS Number: 69-52-3
• EC Number: 200-708-1
• MDL Number: MFCD00064313
• Beilstein Number: 4119211
• PubChem SID: 24891335; 24890405; 162093651; 24890695; 24891463
• PubChem CID: 23663979

CALCULATED PROPERTIES

• Acid pKa: 3.2380536
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.0056438
• LogD (pH = 7.4): -2.2605202
• Log P: -2.0066502
• Molar Refractivity: 98.3606 cm^3
• Polarizability: 34.76069 Å^3
• Polar Surface Area: 115.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL; H2O: soluble50 mg/mL (Stock solutions should be stored at -20 °C.); sterile water: soluble5-20 mg/mL (as a stock solution)
• Apperance: white with slight yellow cast; white with slight yellow cast powder
• Melting Point: 215 °C decomposes; 215 °C (dec.)(lit.)

Safety Information

• Storage Condition: 2-8°C
• RTECS: XH8400000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43; R:22
• Safety Statements: 22-36/37-45; S:36/37/39
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Potency: ≥845 μg per mg
• Suitability: suitable for cell culture
• Impurities: endotoxin, tested
• Sterility: γ-irradiated
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C16H18N3NaO4S

DETAILS

MP Biomedicals - 02194199

Sodium Salt
γ-Irradiated
Molecular Biology Reagent
Inhibits cell wall biosynthesis.

MP Biomedicals - 02190148

Sodium Salt Crystalline

MP Biomedicals - 02194526

Cell Culture Reagent
Sodium Salt
Crystalline

Sigma Aldrich - A2804

Analysis Note
USP potency testing is carried out on control vials after γ-irradiation to assure full biological activity (except where noted).
Application
Recommended for use in molecular biology applications at 20-50 μg/ml.
Biochem/physiol Actions
β-内酰胺类抗生素，具有连接到青霉素结构上的氨基侧链。青霉素衍生物，通过灭活细菌细胞膜内表面上的转肽酶，抑制细菌细胞壁的合成（肽聚糖交联）。仅对生长的 Escherichia coli 具有杀菌作用。抗性方式：通过 β-内酰胺酶使氨苄西林的 β-内酰胺环分裂。抗菌谱：革兰氏阴性和革兰氏阳性细菌。
Reconstitution
Prepare stock solutions directly in the vial at any concentration in the recommended range. Stock solutions should be stored at -20 °C. Stable at 37 °C for 3 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - A8351

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.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - A0166

Application
建议以 100mg/L 的抗菌用量用于细胞培养基中。 建议以 20-125μg/ml 的量用于氨苄西林抗性研究。 在 37°C 下可稳定 3 天。
Biochem/physiol Actions
β-内酰胺类抗生素，具有连接到青霉素结构上的氨基侧链。青霉素衍生物，通过灭活细菌细胞膜内表面上的转肽酶，抑制细菌细胞壁的合成（肽聚糖交联）。仅对生长的 Escherichia coli 具有杀菌作用。抗性方式：通过 β-内酰胺酶使氨苄西林的 β-内酰胺环分裂。抗菌谱：革兰氏阴性和革兰氏阳性细菌。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - A9518

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Used to select for ampicillin resistance in mutated and transformed cells.
Biochem/physiol Actions
β-内酰胺类抗生素，具有连接到青霉素结构上的氨基侧链。青霉素衍生物，通过灭活细菌细胞膜内表面上的转肽酶，抑制细菌细胞壁的合成（肽聚糖交联）。仅对生长的 Escherichia coli 具有杀菌作用。抗性方式：通过 β-内酰胺酶使氨苄西林的 β-内酰胺环分裂。抗菌谱：革兰氏阴性和革兰氏阳性细菌。
包装
5, 25, 100 g in poly bottle