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

• ChemBase编号: 460
• 分子式: C17H18N2O6S
• 平均质量: 378.39962
• 单一同位素质量: 378.08855731
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)C(c1ccccc1)C(=O)O
• Canonical SMILES: O=C(C(c1ccccc1)C(=O)O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1
• InChIKey: FPPNZSSZRUTDAP-UWFZAAFLSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC传统名: carbenicillin
• 商标名: Geopen; Pyopen
• 别名: α-Carboxybenzylpenicillin 溶液; 羧苄青霉素; 羧苄青霉素; 克雷伯氏菌选择性添加剂; Carboxybenzylpenicillin acid; Carboxybenzylpenicillin; Carbenicillinum [INN-Latin]; Carbenicilline [INN-French]; Carbenicillina [DCIT]; Carbenicilina [INN-Spanish]; alpha-Carboxybenzylpencillin; Carbenicillin; α-Carboxybenzylpenicillin solution; Carbenicillin; Carbenicillin; Klebsiella Selective Supplement

登记号

• CAS号: 4697-36-3
• EC号: 225-171-0
• MDL号: MFCD00242604
• PubChem SID: 24892425; 160963923; 46505653
• PubChem CID: 20824

理论计算性质

JChem

• Acid pKa: 3.1068087
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -3.1951313
• LogD (pH = 7.4): -5.9115877
• Log P: 0.81535685
• 摩尔折射率: 90.8195 cm^3
• 极化性: 35.8031 Å^3
• 极化表面积: 124.01 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.13
• LOG S: -2.99
• 溶解度: 3.90e-01 g/l

分子性质

理化性质

• 溶解度: 451 mg/L
• 闪点: 104 °F; 40 °C
• 疏水性(logP): 1.8

安全信息

• RTECS编号: ON9104700
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1170
• 德国WGK号: 2; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 10-42/43; 42/43
• 安全公开号: 22-36/37-45; 23-36/37-45
• GHS危险品标识: GHS02; GHS08
• GHS警示词: Danger
• GHS危险声明: H226-H317-H334; 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; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 3
• 保存温度: -20°C; 2-8°C

产品相关信息

• 浓度: 100 mg/mL in ethanol/water
• 级别: for microbiology
• 无菌消毒: 0.2 μm filtered
• 有效期: (limited shelf life, expiry date on the label)
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C17H18N2O6S

详细说明

DrugBank - DB00578

• Drug Groups: approved
• Description: Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]
• Indication: For the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria.
• Pharmacology: Carbenicillin is a semisynthetic penicillin. Though carbenicillin provides substantial in vitro activity against a variety of both gram-positive and gram-negative microorganisms, the most important aspect of its profile is in its antipseudomonal and antiproteal activity. Because of the high urine levels obtained following administration, carbenicillin has demonstrated clinical efficacy in urinary infections due to susceptible strains of: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Pseudomonas species, Providencia rettgeri, Enterobacter species, and Enterococci (S. faecalis).
• Toxicity: Carbenicillin blood levels achievable are very low, and toxic reactions as a function of overdosage should not occur systematically. The oral LD₅₀ in mice is 3,600 mg/kg, in rats 2,000 mg/kg, and in dogs is in excess of 500 mg/kg. The lethal human dose is not known. Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Minimal.
• Absorption: Rapidly absorbed from the small intestine following oral administration. Oral bioavailability is 30 to 40%.
• Half Life: 1 hour
• Protein Binding: 30 to 60%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - C1613

Application
Used for selection of ampr transformed cells. Use to study the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
Biochem/physiol Actions
羧苄青霉素是氨苄青霉素的类似物，是一种常用的选择剂，它可以结合并抑制细菌细胞壁合成中涉及到的酶。它对耐氨苄青霉素的大多数铜绿假单胞菌分离株以及某些吲哚阳性变形杆菌?均有效。氨苄青霉素及其类似物抗性基因 ampr 编码 β-内酰胺酶。羧苄青霉素比氨苄青霉素对 β-内酰胺酶的敏感性更弱。此外它在低 pH 下具有优异的稳定性。实验表明，用羧苄青霉素替代氨苄青霉素有助于防止卫星菌落的过度生长。有效浓度：50 至 100μg/mL。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 15821

Components
（每瓶，足够用于 500mL 培养基） 羧苄青霉素 25mg
Application
用于选择性分离和检测克雷伯氏菌。
Biochem/physiol Actions
羧苄青霉素是氨苄青霉素的类似物，是一种常用的选择剂，它可以结合并抑制细菌细胞壁合成中涉及到的酶。它对耐氨苄青霉素的大多数铜绿假单胞菌分离株以及某些吲哚阳性变形杆菌?均有效。氨苄青霉素及其类似物抗性基因 ampr 编码 β-内酰胺酶。羧苄青霉素比氨苄青霉素对 β-内酰胺酶的敏感性更弱。此外它在低 pH 下具有优异的稳定性。实验表明，用羧苄青霉素替代氨苄青霉素有助于防止卫星菌落的过度生长。有效浓度：50 至 100μg/mL。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 15821.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.