cefamandole sodium | 30034-03-8

• 物质功能分类: 原料药 - 抗生素类药物 - 头孢菌素类药
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: cefamandole sodium
• 英文别名: cefamandole sodium salt；sodium;(2R)-N-[(6R,7R)-2-carboxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]-2-hydroxy-2-phenylethanimidate
• CAS: 30034-03-8
• 化学式: C₁₈H₁₇N₆O₅S₂*Na
• 分子量: 484.492
• InChiKey: OJMNTWPPFNMOCJ-CFOLLTDRSA-M

物化性质

• 熔点：
  >175°C (dec.)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）
• 碰撞截面：
  195.5 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 稳定性/保质期：
  Moisture Sensitive

计算性质

• 辛醇/水分配系数(LogP)：
  -4.56
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  204
• 氢给体数：
  2
• 氢受体数：
  10

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38,R42/43
• WGK Germany：
  2
• RTECS号：
  XI0389000
• 储存条件：
  库房应保持低温、通风和干燥。

制备方法与用途

用途

头孢孟多钠作为一种第二代头孢菌素类抗生素，在市场中具有巨大的潜力。它常用于治疗由厌氧菌、革兰阳性菌和革兰阴性菌引起的感染。

生物活性

Cefamandole Sodium Salts是一种头孢菌素类抗生素。

用途与类别

头孢孟多钠属于抗生素类药物，归类为低毒物质。其急性毒性较低：静脉注射大鼠的半数致死量（LD50）为4410毫克/公斤；静脉注射小鼠的半数致死量（LD50）为4460毫克/公斤。

特性

• 可燃性危险特性：热分解时会排出有毒的氮氧化物、硫氧化物及氧化钠烟雾。
• 储运特性：应存放在低温通风干燥处。
• 灭火剂：推荐使用水、二氧化碳、泡沫或干粉进行灭火。

反应信息

• 作为反应物：
  描述：

  甘氨酸甲酯盐酸盐 、 cefamandole sodium 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-glycine methyl ester
  参考文献：
  名称：

  Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of aminoacyloxymethyl esters of 7-[D-(-)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid

  摘要：

  The synthesis of six amino acid acyloxymethyl esters of cefamandole (1), a semisynthetic broad-spectrum cephalosporin antibiotic, is described. These esters were examined as potentially useful orally active antibiotic prodrugs. When tested for oral efficacy against Streptococcus pyogenes C203 in mouse protection tests, the esters were not notably more active than lithium cefamandole. Further studies demonstrated that significant blood and urine levels of 1 were not obtained after dosing 2a, 2b, and 2f orally at 17 mg/kg in mice. A study of the stability to chemical hydrolysis and the possible relationship of hydrolysis to the lack of oral absorption of these esters is also presented.

  DOI：

  10.1021/jm00192a010
• 作为产物：
  描述：

  头孢孟多 生成 cefamandole sodium
  参考文献：
  名称：

  SHIBUYA, CHISEI;MURAKAMI, MASAHIRO;KOBAYASHI, MASATERU;SONE, TAKANORI

  摘要：

  DOI：

文献信息

• 1/5水头孢孟多酯钠化合物
  申请人：海南美大制药有限公司

  公开号：CN106699775B

  公开（公告）日：2019-05-10

  本发明公开了1/5水头孢孟多酯钠化合物及其制法，每摩尔头孢孟多酯钠含1/5摩尔水。本发明方法所制备的头孢孟多酯钠化合物，杂质含量低，稳定性好，具有更广泛的应用前景。
• Novel 3-acyloxymethyl-cephem compounds useful as intermediates for
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04245088A1

  公开（公告）日：1981-01-13

  Novel 3-acyloxymethyl-cephem compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen or an acyl group; W is acetonyl, or a group represented by --X--COOH or --X--OH (X is an organic residue) or salts thereof were found to be useful as starting materials for preparing cephalosporins of the formula: ##STR2## wherein R.sup.3 stands for a residue of a nucleophilic compound and R.sup.1 has the same meaning as above.

  该文提出了一种公式为：##STR1##的小分子化合物，其中R1代表氢或酰基；W代表丙酮基，或由—X—COOH或—X—OH（X为有机残基）表示的基团或其盐。这些化合物可以作为制备公式为：##STR2##的头孢菌素的起始材料，其中R3代表亲核化合物的残基，R1具有与上述相同的含义。
• Cephem compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04308381A1

  公开（公告）日：1981-12-29

  Novel 3-acyloxymethyl-cephem compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen or an acyl group; W is acetonyl, or a group represented by --X--COOH or --X--OH (X is an organic residue) or salts thereof were found to be useful as starting materials for preparing cephalosporins of the formula: ##STR2## wherein R.sup.3 stands for a residue of a nucleophilic compound and R.sup.1 has the same meaning as above.

  该文提到了一种公式为：##STR1## 其中R1为氢或酰基；W为乙酰基，或由--X--COOH或--X--OH（X为有机残基）代表的基团或其盐。这些化合物被发现可用作制备公式为：##STR2## 其中R3代表亲核化合物的残基，R1的含义与上述相同的头孢菌素的起始材料。
• Process for preparing cephalosporins
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04323676A1

  公开（公告）日：1982-04-06

  Novel 3-acyloxymethyl-cephem compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen or an acyl group; W is acetonyl, or a group represented by --X--COOH or --X--OH (X is an organic residue) or salts thereof were found to be useful as starting materials for preparing cephalosporins of the formula: ##STR2## wherein R.sup.3 stands for a residue nucleophilic compound and R.sup.1 has the same meaning as above.

  公式为 ##STR1## 的新型3-酰氧甲基头孢菌素化合物，其中R1为氢或酰基；W为乙酰基，或由—X—COOH或—X—OH（X为有机残基）表示的基团或其盐，被发现可作为制备公式为 ##STR2## 的头孢菌素的起始材料，其中R3代表一个亲核化合物残基，R1的含义如上。
• Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of aminoacyloxymethyl esters of 7-[D-(-)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid
  作者：W. J. Wheeler、D. A. Preston、W. E. Wright、G. W. Huffman、H. E. Osborne、D. P. Howard

  DOI：10.1021/jm00192a010

  日期：1979.6

  The synthesis of six amino acid acyloxymethyl esters of cefamandole (1), a semisynthetic broad-spectrum cephalosporin antibiotic, is described. These esters were examined as potentially useful orally active antibiotic prodrugs. When tested for oral efficacy against Streptococcus pyogenes C203 in mouse protection tests, the esters were not notably more active than lithium cefamandole. Further studies demonstrated that significant blood and urine levels of 1 were not obtained after dosing 2a, 2b, and 2f orally at 17 mg/kg in mice. A study of the stability to chemical hydrolysis and the possible relationship of hydrolysis to the lack of oral absorption of these esters is also presented.

表征谱图