sodium;(2R,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• 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: sodium;(2R,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• 化学式: C23H26N5NaO7S
• 分子量: 539.5
• InChiKey: WCMIIGXFCMNQDS-UVINOEOUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.57
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  8

ADMET

毒理性

• 肝毒性

静脉注射哌拉西林的患者中，多达12%的患者可能会出现短暂且轻至中度的血清转氨酶升高，但这些升高的临床意义不大，并不比其他类似的静脉注射抗生素更常见。与哌拉西林相关的广谱脲酶青霉素类药物美洛西林更常报告有肝损伤，该药物已经从市场上撤回。在接受哌拉西林治疗的人中，罕见有个体对肝损伤的特异反应的报道。肝损伤通常是胆汁淤积性的，在开始治疗后的1到6周内发生。这种损伤可能很严重，但一旦停止使用哌拉西林，通常是自限性的。肝毒性的特征与其他青霉素类药物相似。哌拉西林和其他青霉素类药物引起的胆汁淤积性肝炎可能持续时间较长，导致持续性胆汁淤积（消失胆管综合征）或血清碱性磷酸酶持续升高，提示部分胆管丢失。与哌拉西林相关的肝损伤大多数与哌拉西林与β-内酰胺酶抑制剂他唑巴坦（Zosyn及其仿制药）的联合使用有关，这种联合用药比单独使用哌拉西林更为常见。

Patients on intravenous piperacillin may have transient and mild-to-moderate serum aminotransferase elevations in up to 12% of patients, but these are of little clinical significance and not more common than with comparative parenteral antibiotics. Hepatic injury was more commonly reported with mezlocillin, a related extended spectrum ureidopenicillin which has been withdrawn from use. Rare instances of idiosyncratic liver injury have been reported in persons receiving piperacillin. The liver injury is typically cholestatic arising within 1 to 6 weeks of starting therapy. The injury can be severe, but is generally self-limited once piperacillin is stopped. The features of the hepatotoxicity resemble those of other penicillins. The cholestatic hepatitis caused by piperacillin and other penicillins can be prolonged and lead to persistent cholestasis (vanishing bile duct syndrome) or persistent elevations in serum alkaline phosphatase suggestive of partial bile duct loss. Most cases of liver injury related to piperacillin are linked to the combination of piperacillin with the beta-lactamase inhibitor tazobactam (Zosyn and generics), which is more commonly used than piperacillin alone.

来源:LiverTox