56796-20-4

• 常用中文名：头孢美唑
• 常用英文名：Cefmetazole
• CAS号：56796-20-4
• 分子式：C₁₅H₁₇N₇O₅S₃
• 分子量：471.534
• 相关类别： 原料药 抗生素类药物 头孢菌素类药
• 发布时间：2018-07-20 19:19:54
• 更新时间：2024-01-02 12:07:49
• 头孢美唑(CS 1170)是一种半合成的头孢霉素抗生素,具有广谱抗菌活性,包括革兰氏阳性菌、革兰氏阴性菌和厌氧菌。头孢美唑与青霉素结合蛋白(PBPs)结合,干扰细菌细胞壁生物合成。头孢美唑用于研究妇科、腹腔内、泌尿道、呼吸道以及皮肤和软组织感染[1][2][3]。

名称

• 中文名: 头孢甲氧氰唑
• 英文名: cefmetazole
• 中文别名: (6R-cis)-7-[[[(氰甲基)硫]乙酰]氨基]-7-甲氧基-3-[[(1-甲基-1H-四唑-5-基)硫]甲基]-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸; 头孢美唑酸; 头孢美唑
• 英文别名: (6R,7S)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; cefmetazolum [INN_la]; (6R,7S)-7-({[(Cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cefmetazole; 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-; EINECS 260-384-2; 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-; MFCD00214260

物化性质

• 密度: 1.8±0.1 g/cm3
• 熔点: 163-165ºC
• 分子式: C₁₅H₁₇N₇O₅S₃
• 分子量: 471.534
• 精确质量: 471.045319
• PSA: 239.23000
• LogP: 0.97
• 外观性状: 白色固体
• 折射率: 1.798
• 储存条件: 库房低温通风干燥

生物活性

• 描述: 头孢美唑(CS 1170)是一种半合成的头孢霉素抗生素,具有广谱抗菌活性,包括革兰氏阳性菌、革兰氏阴性菌和厌氧菌。头孢美唑与青霉素结合蛋白(PBPs)结合,干扰细菌细胞壁生物合成。头孢美唑用于研究妇科、腹腔内、泌尿道、呼吸道以及皮肤和软组织感染[1][2][3]。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 体外研究: 头孢美唑(CS 1170)对金黄色葡萄球菌具有抗生素亲和力,MIC值为1.0mg/L。头孢美唑对PBP1、PBP2和PBP3具有亲和力,IC50值为≤0.3、0.109和0.494毫克/升[1]。
• 体内研究: 头孢美唑(CS 1170)(100mg/kg；i.h.；每天两次,共7天；雄性ICR小鼠)改变肠道菌群[3]。动物模型：雄性ICR小鼠[3]剂量：100mg/kg给药：皮下注射；一天两次,持续7天。结果：减少派尔斑(PP)淋巴细胞数量,同时减少小肠细菌数量。
• 参考文献:

  [1]. Truesdell SE, et, al. Interaction of cephalosporins with penicillin-binding proteins of methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother. 1989 Apr;23 Suppl D:13-9.

  [2]. Schentag JJ. Cefmetazole sodium: pharmacology, pharmacokinetics, and clinical trials. Pharmacotherapy. 1991;11(1):2-19.

  [3]. Yaguchi Y, et, al. Influences of long-term antibiotic administration on Peyer's patch lymphocytes and mucosal immunoglobulin A levels in a mouse model. JPEN J Parenter Enteral Nutr. 2006 Sep-Oct;30(5):395-8; discussion 399.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : XI0372000 CHEMICAL NAME : 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((((cyanomethyl)thio)acetyl)amino)- 7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl) -8-oxo-, (6R-cis)- CAS REGISTRY NUMBER : 56796-20-4 LAST UPDATED : 199612 DATA ITEMS CITED : 4 MOLECULAR FORMULA : C15-H17-N7-O5-S3 MOLECULAR WEIGHT : 471.57 WISWESSER LINE NOTATION : T46 ANV ES GUTJ CO1 CMV1S1CN HVQ G1S- ET5NNNNJ A1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 10233 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair REFERENCE : SKKNAJ Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories. (Sankyo K.K. Sogo Kenkyusho, 1-2-58 Hiro-machi, Shinagawa-ku, Tokyo 140, Japan) No.15- 1963- Volume(issue)/page/year: 31,49,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 12190 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair REFERENCE : SKKNAJ Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories. (Sankyo K.K. Sogo Kenkyusho, 1-2-58 Hiro-machi, Shinagawa-ku, Tokyo 140, Japan) No.15- 1963- Volume(issue)/page/year: 31,49,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 8690 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair REFERENCE : SKKNAJ Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories. (Sankyo K.K. Sogo Kenkyusho, 1-2-58 Hiro-machi, Shinagawa-ku, Tokyo 140, Japan) No.15- 1963- Volume(issue)/page/year: 31,49,1979 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 9 gm/kg SEX/DURATION : female 18-35 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death REFERENCE : JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 6,289,1980

安全

• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): 26-36
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: XI0372200

合成路线

56023-19-9 ~% 56796-20-4

文献：Journal of Antibiotics, , vol. 29, # 5 p. 554 - 558

60445-97-8 ~% 56796-20-4

文献：Journal of Antibiotics, , vol. 29, # 9 p. 969 - 972

24209-38-9 ~% 56796-20-4

文献：Journal of Antibiotics, , vol. 29, # 9 p. 969 - 972

53090-86-1 ~% 56796-20-4

文献：Journal of Antibiotics, , vol. 29, # 5 p. 554 - 558

52069-55-3 60638-56-4 ~% 56796-20-4

文献：Journal of Antibiotics, , vol. 29, # 9 p. 969 - 972

52069-55-3 56610-72-1 ~% 56796-20-4

文献：Journal of Antibiotics, , vol. 29, # 5 p. 554 - 558