氨苄西林

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 氨苄西林
• 中文别名: 氨苄青霉素；氨苄西林三水酸；哌拉西林杂质A；罗硝唑；三水氨苄西林；氨苄西林三水；氨苄青霉素水合物；氨苄西林三水合物
• 英文名称: 6-[D(-)-alpha-Aminophenylacetamido]penicillanic acid trihydrate
• 英文别名: (2S,5R,6R)-6-[[(2R)-2-azaniumyl-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;trihydrate
• 化学式: C16H25N3O7S
• 分子量: 403.5
• InChiKey: RXDALBZNGVATNY-CWLIKTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.16
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  141
• 氢给体数：
  6
• 氢受体数：
  9

ADMET

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用总结：大量信息表明，氨苄青霉素在乳汁中产生的水平较低，预计不会对哺乳婴儿造成不良影响。偶尔有报道称青霉素会破坏婴儿的胃肠道菌群，导致腹泻或鹅口疮，但这些影响尚未得到充分评估。氨苄青霉素在哺乳母亲中是可以接受的。 ◉ 对哺乳婴儿的影响：在一项非控制观察中，服用氨苄青霉素的哺乳母亲的婴儿中似乎出现了腹泻和念珠菌病增加的情况，这被归因于母乳中的氨苄青霉素。[7] 在一项前瞻性随访研究中，5位哺乳母亲报告服用氨苄青霉素（剂量未指定）。一位母亲报告她的婴儿出现腹泻。暴露的婴儿中没有报告出现皮疹或念珠菌病。[8] 在一项小型、受控的前瞻性研究中，让母亲监测她们的婴儿是否有不良反应的迹象（舌头起毛、喂养困难、大便频率和质地的变化、尿布疹和皮肤疹）。还记录了体重变化和黄疸的发展。在这些参数上，对照组母亲的婴儿和服用氨苄青霉素的母亲的婴儿之间没有发现统计差异。[9] ◉ 对泌乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:Substantial information indicates that ampicillin produces low levels in milk that are not expected to cause adverse effects in breastfed infants. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with penicillins, but these effects have not been adequately evaluated. Ampicillin is acceptable in nursing mothers. ◉ Effects in Breastfed Infants:An uncontrolled observation of the breastfed infants of mothers taking ampicillin noted a seeming increase in cases of diarrhea and candidiasis that was attributed to ampicillin in breastmilk.[7] In a prospective follow-up study, 5 nursing mothers reported taking ampicillin (dosage unspecified). One mother reported diarrhea in her infant. No rashes or candidiasis were reported among the exposed infants.[8] A small, controlled, prospective study had mothers monitor their infants for signs of adverse effects (furring of the tongue, feeding difficulties, changes in stool frequency and consistency, diaper rash, and skin rash). Weight change and the development of jaundice were also recorded. No statistical differences in these parameters were found between the infants of the control mothers and those of mothers taking ampicillin.[9] ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

反应信息

• 作为反应物：
  描述：

  氨苄西林 、 sodium hydroxide 以 水 为溶剂， 以the sodium ampicillin was isolated in exactly the same manner as in Example 1的产率得到ampicillin sodium salt
  参考文献：
  名称：

  Process for preparation of alkali metal salts of ampicillin

  摘要：

  一种制备氨苄青霉素碱金属盐（尤其是钠盐）的方法，包括将等摩尔或稍少量的碱金属碱溶液加入不超过约4℃的氨苄青霉素水悬浮液中，过滤所得的溶液直至无菌，冷冻滤液，然后进行冻干。

  公开号：

  US04130558A1
• 作为产物：
  描述：

  氨苄西林 、 、 盐酸 在 ice 、 盐酸 、 水 、 氨苄西林 、 氨 作用下， 反应 0.5h， 生成 氨苄西林
  参考文献：
  名称：

  Beta lactam production

  摘要：

  本文介绍了一种新的生产6-α-氨基青霉素和7-α-氨基去乙酰头孢菌素的方法，该方法不含卤素溶剂，通过在无卤素溶剂中对6-APA、7-ADCA或其衍生物进行酰化来实现。

  公开号：

  US05719276A1
• 作为试剂：
  描述：

  、 、 氨苄西林 、 、 盐酸 在 ice 、 水 、 盐酸 、 sodium hydroxide 、 氨苄西林 、 异丙醇 作用下， 反应 18.33h， 生成 氨苄西林
  参考文献：
  名称：

  Silylation process

  摘要：

  一种将6-氨基青霉烷酸或7-氨基脱乙酰基头孢菌素酸硅化的方法，该方法是在某些羧酸酯中进行硅化，并且可用于生产6-α-氨基酰基青霉素和7-α-氨基酰基脱乙酰基头孢菌素。

  公开号：

  US05998610A1

文献信息

• Ampicillin derivatives substituted by heterocyclic acyl group
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US03953428A1

  公开（公告）日：1976-04-27

  The ampicillin derivatives represented by the general formula ##SPC1## Wherein R represents ##SPC2## Wherein R' represents a hydrogen atom, a methyl group, or an ethyl group and A and B each represents a hydrogen atom, a hydroxyl group, a methyl group, a methoxy group, a nitro group, or a halogen atom and further said B may combine with A on the carbon atom at the position to form ##SPC3## Group (where in Z represents --CH=N-- or --CH=CH-- and an R.sup.2 represents a hydrogen atom, a hydroxyl group, a phenyl group, a methyl group, an ethyl group, a methoxy group, an ethoxyl group, a methylthio group, a trifluoromethyl group, a halogen atom, a nitro group, an acetyl group, an acetamido group, a ethoxycarbonyloxy group, or a methylsulfonyl group and further R.sub.2 and ##SPC4## May form a thiazole, isothiazolo, pyrrolo, furo, or benzo fused ring which may be substituted by an oxo group, a methyl group, or an acetyl group) and the dotted line means an arbitrary double bond, ##SPC5## Wherein R.sup.3 and R.sup.4 each represents a hydrogen atom or a methyl group, ##SPC6## Wherein R.sup.5 represents a halogen atom, a methoxy group, a nitro group, or a hydroxyl group and R.sup.6 represents a hydrogen atom, a methoxy group, a halogen atom, a nitro group, or a hydroxyl group, or ##SPC7## Wherein R.sup.7 represents a hydrogen atom or a hydroxyl group, Y represents O or S, and the dotted line means an arbitrary double bond, said substituent group, being bonded to the ampicillin molecule through --CO-- at the 2-position, 3-position, 5-position or 6-position when the oxo group (+0) is at the 4-portion and being bonded to the ampicillin molecule through the --CO-- group at the 2-position, 4-position, or 5-position when the oxy group is at the 6-position, and salts of the ampicillin derivatives. Those compounds are valuable as antibacterial agents.

  该专利描述了氨苄青霉素衍生物的一般公式，其中R代表一种化合物，R'代表氢原子，甲基基团或乙基基团，A和B分别代表氢原子，羟基，甲基，甲氧基，硝基或卤素原子，进一步地，B可以与A在碳原子上结合形成一个羰基，其中Z代表--CH=N--或--CH=CH--，R2代表氢原子，羟基，苯基，甲基，乙基，甲氧基，乙氧基，甲硫基，三氟甲基，卤素原子，硝基，乙酰基，乙酰胺基，乙氧羰氧基，或甲基磺酰基，进一步地R2和R3可以形成噻唑，异噻唑，吡咯，呋喃或苯并融合环，该环可以被氧基，甲基或乙酰基取代。虚线表示任意双键。该专利还描述了这些化合物的盐。这些化合物作为抗菌剂具有重要价值。
• Penicillins
  申请人：Beecham Group Limited

  公开号：US04081545A1

  公开（公告）日：1978-03-28

  A class of .alpha.-(heterocyclic carbonylamino) penicillins in which the heterocyclic group of the acyl moiety is a fused bicyclic ring having a nitrogen atom at the bridge position, shows good antibacterial activity.

  一类α-(杂环羰基氨基)青霉素类化合物，其中酰基部分的杂环基团是一个带有桥位氮原子的融合双环环，表现出良好的抗菌活性。
• Antibodies for penicilloic acid their preparation and use
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04596768A1

  公开（公告）日：1986-06-24

  Conjugates of penicilloic acid derivatives and certain poly(amino acids), which are either antigenic or enzymatic, are provided. Antibodies raised against the antigenic poly(amino acids) and the enzyme conjugates are used as reagents in immunoassays. In particular, the compounds of the present invention can be used for measuring the presence of a .beta.-lactamase in a patient serum sample by adding a known amount of penicillin to the sample and observing the production of penicilloic acid over a fixed period of time.

  提供了青霉素酸衍生物和某些聚（氨基酸）的共轭体，它们或者是抗原性的或者是酶性的。对抗原性聚（氨基酸）和酶共轭体所产生的抗体可用作免疫测定中的试剂。特别地，本发明的化合物可用于通过向样品中加入已知量的青霉素并在固定时间内观察青霉素酸的产生来测量患者血清样品中β-内酰胺酶的存在。
• Process for preparing sultamicillin and analogs
  申请人：Pfizer Inc.

  公开号：US04868297A1

  公开（公告）日：1989-09-19

  6-Halo- and 6,6-dihalo-1,1-dioxopenicillanoyloxymethyl 6-[D-2-(2-alkoxycarbonyl-1-methylvinylamino- and 1-methyl-3-oxo-1-butenylamino)-2-phenylacetamido]penicillanates and analogs; process for their conversion to sultamicillin and analogs; and process for their preparation.

  6-卤代和6,6-二卤代-1,1-二氧代青霉烷酰氧甲基6-[D-2-(2-烷氧羰基-1-甲基乙烯基氨基和1-甲基-3-酮基-1-丁烯基氨基)-2-苯乙酰氨基]青霉素酸酯及其类似物；将其转化为舒巴坦和类似物的过程；以及其制备过程。
• Beta lactam production
  申请人：Biochemie Gesellschaft m.b.H.

  公开号：US05719276A1

  公开（公告）日：1998-02-17

  A new process is described for the production of 6-alpha-amino-penicillins and 7-alpha-amino-desacetoxy-cephalosporins free from halogen-containing solvents by acylating 6-APA, 7-ADCA or a derivative thereof in a halogen-free solvent.

  本文介绍了一种新的生产6-α-氨基青霉素和7-α-氨基去乙酰头孢菌素的方法，该方法不含卤素溶剂，通过在无卤素溶剂中对6-APA、7-ADCA或其衍生物进行酰化来实现。