penicillin-V | 87-08-1

• 物质功能分类: 原料药 - 抗生素类药物 - 青霉素类药
• 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: penicillin-V
• 英文别名: penicillin V.；6β-(2-phenoxy-acetylamino)-penicillanic acid；6-(Phenoxyacetyl-amino)-penicillansaeure；Phenoxymethyl-penicillin K；Phenoxymethyl-penicillin；Phenoxlmethylpenicillin；3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid；3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 87-08-1；6153-24-8；6153-25-9；39539-54-3；41400-52-6；145920-47-4
• 化学式: C₁₆H₁₈N₂O₅S
• mdl: MFCD00807886
• 分子量: 350.395
• InChiKey: BPLBGHOLXOTWMN-UHFFFAOYSA-N

物化性质

• 熔点：
  120-1280C (dec)
• 沸点：
  681.4±55.0 °C(Predicted)
• 密度：
  1.3121 (rough estimate)
• 溶解度：
  极微溶于水，溶于乙醇（96%）。
• 稳定性/保质期：
  稳定，易燃，与强氧化剂不相容。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

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：有限的信息表明，青霉素V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。青霉素V对哺乳母亲是可接受的。 ◉ 对哺乳婴儿的影响：在一项研究中，12名婴儿在母亲接受青霉素V治疗期间进行了母乳喂养。其中7名婴儿看起来正常，3名婴儿大便比正常松散，1名婴儿在治疗的最后一天臀部出现了皮疹。这些影响可能与乳汁中的青霉素V有关，但没有设置对照组。一名婴儿大便中有血迹，但这发生在母亲接受青霉素V治疗之前。 ◉ 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:Limited information indicates that penicillin V 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. Penicillin V is acceptable in nursing mothers. ◉ Effects in Breastfed Infants:In one study, 12 infants were breastfed during maternal penicillin V therapy. Seven appeared normal, 3 had looser stools than normal, and 1 had a rash on the buttocks on the last day of therapy. These effects were possibly related to penicillin V in milk, but no control group was present. One infant had stains of blood in the stool, but it had happened once prior to maternal penicillin V treatment. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36
• 危险类别码：
  R42/43
• 海关编码：
  3003101300
• 危险品运输编号：
  25kgs
• 储存条件：
  -20°C

制备方法与用途

青霉素V（苯氧甲基青霉素）是一种有效的口服抗生素，对链球菌、艰难梭菌和金黄色葡萄球菌具有抗菌活性。研究表明，青霉素V在治疗中耳炎、鼻窦炎、咽炎和扁桃体炎方面有潜在效果。

反应信息

• 作为反应物：
  描述：

  penicillin-V 在 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 生成 tetrabutylammonium S-((2S,3S)-2-acetoxy-4-oxo-3-(2-phenoxyacetamido)azetidin-1-yl) sulfurothioate
  参考文献：
  名称：

  Reactions of (2-oxo-1-azetidinyl)-thiophthalimides with nucleophiles

  摘要：

  DOI：

  10.1016/s0040-4039(00)84724-3

文献信息

• CEPHALOSPORIN DERIVATIVES AND METHODS OF USE
  申请人：UNIVERSITY OF KANSAS

  公开号：US20150322087A1

  公开（公告）日：2015-11-12

  This invention provides cephalosporin derivatives for killing or inhibiting the spread of microorganisms such as non-replicating Mycobacterium tuberculosis and in the treatment of infectious disease.

  本发明提供头孢菌素衍生物，用于杀灭或抑制微生物的扩散，例如非复制的结核分枝杆菌，并用于治疗传染病。
• Process for preparing penicillin sulfoxides
  申请人：ELI LILLY AND COMPANY

  公开号：EP0017419A1

  公开（公告）日：1980-10-15

  A 4-thia-1-azobicyclo (3.2.0) heptane nucleus bearing compound, e.g. a penicillin, is treated with a peroxymonosulfate at from about 0°C to about 50°C in an aqueous medium to form the compound having the corresponding 4-sulfoxide nucleus.

  在水性介质中，用过氧化单硫酸盐在约 0°C 至约 50°C 的温度下处理含 4-硫杂-1-氮杂双环(3.2.0)庚烷核的化合物，如青霉素，以形成具有相应 4-亚砜核的化合物。
• Cephalosporin derivatives and methods of use
  申请人：University of Kansas

  公开号：US10059722B2

  公开（公告）日：2018-08-28

  This invention provides cephalosporin derivatives for killing or inhibiting the spread of microorganisms such as non-replicating Mycobacterium tuberculosis and in the treatment of infectious disease.

  本发明提供的头孢菌素衍生物可用于杀灭或抑制微生物（如不复制的结核分枝杆菌）的传播，并可用于治疗传染病。
• Methods and compositions for polypeptide engineering
  申请人：Patten A. Phillip

  公开号：US20070031878A1

  公开（公告）日：2007-02-08

  Methods are provided for the evolution of proteins of industrial and pharmaceutical interest, including methods for effecting recombination and selection. Compositions produced by these methods are also disclosed.
• METHODS AND COMPOSITIONS FOR POLYPEPTIDE ENGINEERING
  申请人：Patten Phillip A.

  公开号：US20120015820A1

  公开（公告）日：2012-01-19

  Methods are provided for the evolution of proteins of industrial and pharmaceutical interest, including methods for effecting recombination and selection. Compositions produced by these methods are also disclosed.