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

• ChemBase编号: 153576
• 分子式: C16H17KN2O5S
• 平均质量: 388.47988
• 单一同位素质量: 388.04952433
• SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COc1ccccc1)C(=O)[O-])C.[K+]
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)COc1ccccc1.[K+]
• InChI: InChI=1S/C16H18N2O5S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
• InChIKey: HCTVWSOKIJULET-LQDWTQKMSA-M

名称和登记号

名称

• IUPAC标准名: potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC传统名: potassium phenoxymethylpenicillin(1-)
• 别名: 苯氧甲基青霉素 钾盐; 青霉素 V 钾盐; 青霉素 V 钾盐; Phenoxymethylpenicillinic acid potassium salt; Phenoxymethylpenicillin potassium salt; Phenoxymethylpenicillinic acid potassium salt; Penicillin V potassium salt; Penicillin V potassium salt; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Potassium; 6-(Phenoxyacetamido)penicillanic Acid Potassium; Antibiocin; Calciopen K; Cilacil; Fenoxypen; Vepicombin; Penicillin V Potassium Salt

登记号

• CAS号: 132-98-9
• EC号: 205-086-5
• MDL号: MFCD00051771
• Beilstein号: 3899451
• PubChem SID: 24870330; 24898194; 162247715; 24898501
• PubChem CID: 23676814

理论计算性质

• Acid pKa: 3.390268
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): -1.3336357
• LogD (pH = 7.4): -2.6421306
• Log P: 0.7632417
• 摩尔折射率: 96.6051 cm^3
• 极化性: 33.95466 Å^3
• 极化表面积: 98.77 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol; Water
• 外观: powder; White Solid
• 熔点: 234-238°C (dec)

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: XH9275000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-42/43
• 安全公开号: 22-26-36/37-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H317-H334
• GHS警示性声明: P261-P280-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

• 级别: VETRANAL™, analytical standard
• 药效: ≥1460 units per mg
• 活性: ~1,500 U/mg
• 适用性: suitable for 1694 per US EPA; suitable for cell culture
• 产品线: BioReagent
• 线性分子式: C16H17N2O5SK
• Empirical Formula (Hill Notation): C16H17N2O5SK

详细说明

Sigma Aldrich - P1382

Application
Phenoxymethylpenicillinic acid, also known as Penicillin V, is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V is a penicillin β-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. It is commonly used in cell culture in combination with streptomcyin and other antibiotics. It is used to study penicillin-binding protein 21, molecular cloning of the Bacillus sphaericus penicillin V amidase gene2, and gastrointestinal persistence and bile tolerance of Listeria monocytogenes3.
Biochem/physiol Actions
Phenoxymethylpenicillinic acid binds to specific penicillin-binding proteins (PBPs) and inhibits the synthesis of bacterial cell walls by preventing cell wall peptidoglycan chain cross-linking. This causes cell lysis, which is mediated by autolytic enzymes such as autolysins. Phenoxymethylpenicillnic acid may interfere with autolysin inhibitors.
Phenoxymethylpenicillinic acid inhibits the synthesis of bacterial cell walls by preventing cell wall peptidoglycan chain cross-linking. It is commonly used in cell culture in combination with streptomcyin and other antibiotics.

Sigma Aldrich - P4807

Biochem/physiol Actions
Penicillin V inhibits the synthesis of bacterial cell walls by blocking cell wall peptidoglycan chain cross-linking. Used in cell culture in combination with streptomcyin and other antibiotics.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 46616

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P223500

Antibacterial.

参考文献

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Dunham, J.M., et al.: Anal. Profiles Drug Subs., 1, 249 (1971)