carbenicillin disodium salt

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: carbenicillin disodium salt
• 英文别名: carbenicillin disodium；disodium carbenicillin；sodium;(2S,5R,6R)-6-[(2-carboxylato-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• 化学式: C₁₇H₁₆N₂O₆S*2Na
• 分子量: 422.369
• InChiKey: CNLSIVKXSBRGQP-GJUCOGTPSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -5.18
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  carbenicillin disodium salt 以 MiliQ water 为溶剂， 生成 羧苄西林
  参考文献：
  名称：

  MODIFIED TNFalpha MOLECULES, DNA ENCODING SUCH MODIFIED TNFalpha MOLECULES AND VACCINES COMPRISING SUCH MODIFIED TNFalpha MOLECULES AND DNA

  摘要：

  公开号：

  EP0975668B1

文献信息

• Recycling Antibiotics into GUMBOS: A New Combination Strategy to Combat Multi-Drug-Resistant Bacteria
  作者：Marsha Cole、Jeffery Hobden、Isiah Warner

  DOI：10.3390/molecules20046466

  日期：——

  The emergence of multi-drug-resistant bacteria, coupled with the lack of new antibiotics in development, is fast evolving into a global crisis. New strategies utilizing existing antibacterial agents are urgently needed. We propose one such strategy in which four outmoded β-lactam antibiotics (ampicillin, carbenicillin, cephalothin and oxacillin) and a well-known antiseptic (chlorhexidine di-acetate) were fashioned into a group of uniform materials based on organic salts (GUMBOS) as an alternative to conventional combination drug dosing strategies. The antibacterial activity of precursor ions (e.g., chlorhexidine diacetate and β-lactam antibiotics), GUMBOS and their unreacted mixtures were studied with 25 clinical isolates with varying antibiotic resistance using a micro-broth dilution method. Acute cytotoxicity and therapeutic indices were determined using fibroblasts, endothelial and cervical cell lines. Intestinal permeability was predicted using a parallel artificial membrane permeability assay. GUMBOS formed from ineffective β-lactam antibiotics and cytotoxic chlorhexidine diacetate exhibited unique pharmacological properties and profound antibacterial activity at lower concentrations than the unreacted mixture of precursor ions at equivalent stoichiometry. Reduced cytotoxicity to invasive cell types commonly found in superficial and chronic wounds was also observed using GUMBOS. GUMBOS show promise as an alternative combination drug strategy for treating wound infections caused by drug-resistant bacteria.

  多药耐药细菌的出现，加上新抗生素研发的缺乏，正迅速演变成一场全球危机。迫切需要利用现有抗菌剂的新策略。我们提出了一种策略，利用四种过时的β-内酰胺抗生素（阿莫西林、卡贝西林、头孢噻吩和克拉维酸）以及一种著名的防腐剂（双乙酰氯己定），将其制成基于有机盐的均匀材料组合（GUMBOS），以作为传统组合药物给药策略的替代方案。我们使用微量稀释法对25种具有不同抗生素耐药性的临床分离株，研究了前体离子（如双乙酰氯己定和β-内酰胺抗生素）、GUMBOS及其未反应混合物的抗菌活性。通过纤维芽细胞、内皮细胞和宫颈细胞系确定急性细胞毒性和治疗指数。肠道渗透性通过平行人工膜渗透性测定进行预测。由无效的β-内酰胺抗生素和具有细胞毒性的双乙酰氯己定形成的GUMBOS表现出独特的药理特性，并在比等当量前体离子未反应混合物更低的浓度下展现出显著的抗菌活性。使用GUMBOS时还观察到对常见于表浅和慢性创伤的侵袭性细胞类型的细胞毒性降低。GUMBOS在治疗由耐药细菌引起的创伤感染方面显示出作为替代组合药物策略的潜力。
• Studies at the ionizable position of cephalosporins and penicillins: hydroxamates as substitutes for the traditional carboxylate group
  作者：Mark W Majewski、Patricia A Miller、Marvin J Miller

  DOI：10.1038/ja.2016.149

  日期：2017.3

  Classically, β-lactams need an ionizable group to potentiate antibacterial activity. Sets of cephalosporins and penicillins featuring different substituted hydroxamates in place of the traditional carboxylate group have been synthesized and tested for antibiotic activity. Many of the compounds exhibited anti-bacterial activities with notable MIC values in the range of 6-0.2 μM.

  典型地，β-内酰胺需要一个可电离的基团来增强抗菌活性。合成了以不同取代的羟肟酸盐代替传统羧酸盐基团的头孢菌素和青霉素组，并测试了其抗生素活性。许多化合物显示出抗菌活性，其MIC值在6-0.2μM范围内。
• Aminoglycoside antibiotics. 6. Chemical reactions of aminoglycosides with disodium carbenicillin
  作者：Bhashyam S. Iyengar、Virendra Kumar、Timothy P. Wunz、William A. Remers

  DOI：10.1021/jm00155a004

  日期：1986.5

  Aminoglycoside antibiotics including kanamycin A, tobramycin, and the gentamicin C complex reacted with 1 mol of disodium carbenicillin to give products derived from acylation of their amino groups by the beta-lactam function of the carbenicillin. Amikacin was acylated by two carbenicillin units. Chromatographic analysis of fragments from the acid hydrolysis of these derivatives showed that the preferred

  氨基糖苷类抗生素（包括卡那霉素A，妥布霉素和庆大霉素C配合物）与1摩尔羧苄青霉素二钠反应，生成通过羧苄青霉素的β-内酰胺功能对其氨基进行酰化得到的产物。阿米卡星被两个羧苄青霉素单元酰化。对这些衍生物进行酸水解后得到的片段进行色谱分析表明，酰化的优选位点位于氨基糖苷的2-脱氧链胺胺单元中。阿米卡星中的两个酰化位点是6'-氨基和氨基羟基丁酰基取代基中的氨基。衍生物几乎没有抗菌活性，并且无毒。
• Process for the preparatin of .beta.-lactam compounds
  申请人：Beecham Group plc.

  公开号：US05750684A1

  公开（公告）日：1998-05-12

  The present invention provides a process for the substitution of an acylamino .beta.-lactam compound at the carbon atom carrying the acylamino group, which process comprises reacting the .beta.-lactam compound with an halogenating agent and a nucleophilic reagent; characterized in that the acylamino group has an acidic group on the carbon atom adjacent the carbonyl group. In particular the process of this invention comprises reacting a .beta.-lactam of partial structure (I): ##STR1## where X represents an acidic group; with an halogenating agent and a nucleophilic reagent.

  本发明提供一种用于在携带酰胺基团的碳原子上替代酰胺基团的β-内酰胺化合物的过程，该过程包括将β-内酰胺化合物与卤化剂和亲核试剂反应；其特征在于酰胺基团在相邻羰基的碳原子上具有酸性基团。具体而言，本发明的过程包括将部分结构（I）的β-内酰胺（I）与卤化剂和亲核试剂反应，其中X代表酸性基团。
• [EN] ANTISEPTIC-ANTIBIOTIC GUMBOS EFFECTIVE AGAINST GRAM-NEGATIVE PATHOGENS<br/>[FR] GUMBOS ANTISEPTIQUE-ANTIBIOTIQUE EFFICACES CONTRE DES PATHOGÈNES GRAM-NÉGATIFS
  申请人：UNIV LOUISIANA STATE

  公开号：WO2021183590A1

  公开（公告）日：2021-09-16

  Ion-pairs known as GUMBOS (group of uniform materials based on organic salts) from antiseptics (chlorhexidine and octenidine) and the beta-lactam antibiotic, ceftriaxone. The antimicrobial efficacy of these GUMBOS and unreacted stoichiometric equivalent mixtures were compared to ceftriaxone and azithromycin alone. On a molar basis, GUMBOS were equivalent to ceftriaxone and 10X more effective in killing N. gonorrhoeae than azithromycin. They were more than 100X more effective than either antibiotic in killing CRE. A strategy involving the electrostatic interaction between a common antiseptic and a discontinued antibiotic (octenidine and carbenicillin) was also evaluated as a treatment for gonorrhoea. Octenidine/ carbenicillin is a novel group of uniform materials based on organic salts (GUMBOS) with inherent in vitro antibacterial activity that comes from its parent antiseptic and antibacterial ions, octenidine and carbenicillin, respectively.

  离子对被称为GUMBOS（基于有机盐的一致性材料组）来自于消毒剂（氯己定和辛甘露醇）和β-内酰胺类抗生素头孢曲松。将这些GUMBOS和未反应的化学计量等量混合物与头孢曲松和阿奇霉素单独进行抗菌效果比较。按摩尔计算，GUMBOS相当于头孢曲松，并且比阿奇霉素更有效地杀死N. gonorrhoeae，效果提高了10倍。它们杀死CRE的效果比任何抗生素都高100倍以上。还评估了一种涉及常用消毒剂和停用抗生素（辛甘露醇和氨苄青霉素）之间静电相互作用的策略作为淋病的治疗方法。Octenidine/carbenicillin是一种新型的基于有机盐的一致性材料组（GUMBOS），它具有内在的体外抗菌活性，来自于其母体消毒剂和抗菌离子，分别是辛甘露醇和氨苄青霉素。