32887-01-7

• 常用中文名：美西林
• 常用英文名：Mecillinam
• CAS号：32887-01-7
• 分子式：C₁₅H₂₃N₃O₃S
• 分子量：439.569
• 相关类别： 原料药 抗生素类药物 青霉素类药
• 发布时间：2018-03-11 08:00:00
• 更新时间：2026-06-30 10:48:31
• Mecillinam (Amdinocillin) 是一种β 内酰胺类抗生素,具有广谱的抗革兰氏阴性菌的活性。

名称

• 中文名: 美西林
• 英文名: mecillinam
• 中文别名: 脒青霉素; (2S,5R,6R)-6-(氮杂卓烷-1-基亚甲基氨基)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸; 化合物：Mecillinam; 氮脒青霉素; 氮卓脒青霉素(美西林); 学名:[2S-(2Α,5Α,6Β)]-6-[[(六氢-1H-氮杂革-1-基)甲烯基]氨基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸; 氮革脒青霉素; 美西林-[13C6]/精确称量; 化合物:Mecillinam; 氮卓脒青霉素; (2S,5R,6R)-6-(((E)-氮杂-1-基亚甲基)氨基)-3,3-二甲基-7-氧代-4-噻-1-氮杂双环[3.2.0]庚烷-2-羧酸; Mecillinam 美西林; 美西林/ Mecillinam; 美西林 盐酸; 美西林/氮脒青霉素; 13C6]-美西林
• 英文别名: Amdinocillin (Mecillinam; 13C6]-Mecillinam; Mecillinam (t; Mecillinam ( product); [(2,2-Dimethylpropanoyl)oxy]methyl (5R,6R)-6-[(E)-(1-azepanylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; fl1060; MecillinamQ: What is Mecillinam Q: What is the CAS Number of Mecillinam Q: What is the storage condition of Mecillinam; MECILLINAM HYDROCHLORIDE; penicillinhx; [6R]-6-[Perhydroazin-1-yl-methyleneamino] penicillanic acid; (2S,5R,6R)-6-(Azan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid; Mecillinam D12; Mecillinam, FL-1060, Ro-9070; Mecillinam //BP; Mecillinam D3; Coactin; FL10606; 6-((hexahydro-1h-azin-1-yl)methyleneamino)penicillanicacid; (2S,5R,6R)-6-[[(Hexahydro-1H-azin-1-yl)Methylene]amino]-3,3-diMethyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]htane-2-cboxylic Acid; (2S,5R,6R)-6-[(Azan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid; mecilinamo; Mecillinam, Antibiotic for Culture Media Use Only; (+)-yl)methylene)amino); 4-thia-1-azabicyclo(3.2.0)htane-2-cboxylicacid,6-(((hexahydro-1h-azin-1; Selexidin; FL-1060, Ro-9070, MecillinaM, 6-[[(Hexahydro-1H-azin-1-yl)Methylene]amino]penicillanic Acid; Amdinocillin (~); Amdinocillin; EINECS 251-277-1; Mecill·Nam; MFCD00056869; ro10-9070; Mecillinamum; MECILLINAM; (2S,5R,6R)-6-(((E)-Azan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid; Hexapen; AMDINOCILLIN; [2S-(2α，5α，6β)]-6-[[(Hexahydro-1h-azin-1-y1)methylene]amino]-3，3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid; Mecillinam VETRANAL; hexacillin; 4-Thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid, 6-[[(hexahydro-1H-azin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R); 6-(1-azanylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 581.0±60.0 °C at 760 mmHg
• 熔点: 156°C
• 分子式: C₁₅H₂₃N₃O₃S
• 分子量: 439.569
• 闪点: 305.2±32.9 °C
• 精确质量: 439.214081
• PSA: 98.51000
• LogP: 2.97
• 外观性状: 白色固体
• 蒸汽压: 0.0±1.6 mmHg at 25°C
• 折射率: 1.604
• 储存条件: Store at?0-5°C
• 分子结构:

  1、 摩尔折射率：85.52

  2、 摩尔体积（cm³/mol）：224.8

  3、 等张比容（90.2K）：623.4

  4、 表面张力（dyne/cm）：59.1

  5、 极化率（10-24cm3）：33.90

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:5

  4.可旋转化学键数量:3

  5.互变异构体数量:2

  6.拓扑分子极性表面积98.5

  7.重原子数量:22

  8.表面电荷:0

  9.复杂度:500

  10.同位素原子数量:0

  11.确定原子立构中心数量:3

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：无色结晶，无臭无味。

  2.熔点：156℃(分解)。

  3.折射率：[a]_D²⁰+285°(C=1，0.1mol/L盐酸)。

  4.溶解度：易溶于水，略溶于乙醇，微溶于丙酮，难溶于乙醚或异丙醇。

生物活性

• 描述: Mecillinam (Amdinocillin) 是一种β 内酰胺类抗生素,具有广谱的抗革兰氏阴性菌的活性。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 体内研究: 美西林(Amdinocillin,400 mg/kg)对高剂量(400 mg/kg体重/d)的导管相关感染有效[1]。动物模型：美西林(Amdinocillin,400mg/kg)对高剂量(400mg/kg体重/d)的导管相关性感染有效[1]。剂量：每公斤50、100、200和400毫克。给药：每天静脉注射,分四次,持续72小时。结果：大剂量400mg/kg具有显著的活性。
• 参考文献:

  [1]. M E Olson, et al. Amdinocillin Treatment of Catheter-Associated Bacteriuria in Rabbits. J Infect Dis. 1989 Jun;159(6):1065-72.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : XI0185000 CHEMICAL NAME : 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1H-azepin-1-yl)methylene) amino)-3,3-dimethyl-7-oxo-, (+)- CAS REGISTRY NUMBER : 32887-01-7 LAST UPDATED : 199512 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C15-H23-N3-O3-S MOLECULAR WEIGHT : 325.47 WISWESSER LINE NOTATION : T45 ANV ESTJ F1 F1 GVQ CNU1- AT7NTJ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - ataxia REFERENCE : EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >4 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - ataxia REFERENCE : EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1500 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 16,191,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >20 gm/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea REFERENCE : EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3500 mg/kg TOXIC EFFECTS : Blood - other changes REFERENCE : EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1200 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 16,191,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 130 gm/kg/26W-I TOXIC EFFECTS : Blood - normocytic anemia Liver - changes in liver weight Related to Chronic Data - changes in testicular weight REFERENCE : EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980

安全

• 个人防护装备: Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危害码 (欧洲): Xi
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): S26
• 危险品运输编码: NONH for all modes of transport
• RTECS号: XI0185000

合成路线

551-16-6 65009-95-2 ~% 32887-01-7

文献：Chemical and Pharmaceutical Bulletin, , vol. 35, # 2 p. 642 - 646

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制备

方法1：氮杂革和三氯乙醛作用，在氮上引入甲酰基，在硫酸二甲酯作用下形成缩醛，和6-APA反应使6-APA上6位上的氨基形成Schiff’S碱，即为美西林。
方法2：6-APA和六甲基硅烷反应，在6-APA6位的氨基上形成三甲硅基，然后和N-甲酰基氮杂革在三乙胺存在下反应，得到美西林。