阿替卡因 | 23964-58-1

• 物质功能分类: 原料药 - 麻醉剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 阿替卡因
• 中文别名: 噻吩卡因；醋氯芬酸杂质H；卡铁卡；4-甲基-3-[[1-氧代-2-(丙氨基)丙基]氨基]-2-噻吩羧酸甲酯
• 英文名称: articaine
• 英文别名: carticaine；(RS)-methyl 4-methyl-3-(2-propylaminopropanoylamino)thiophene-2-carboxylate；3-(N-propyl-2-amino-propionylamino)-2-carbomethoxy-4-methylthiophene；methyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate
• CAS: 23964-58-1
• 化学式: C₁₃H₂₀N₂O₃S
• mdl: MFCD00864454
• 分子量: 284.379
• InChiKey: QTGIAADRBBLJGA-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  bp0.3 162-167°
• 密度：
  1.178±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  5

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：目前没有关于在母乳喂养期间使用阿替卡因的信息。基于其他局部麻醉药进入母乳的排泄量较低，在母乳喂养期间注射单剂量的阿替卡因不太可能对哺乳婴儿产生不利影响。然而，尤其是当哺育新生儿或早产儿时，可能更倾向于使用其他药物。 ◉ 对哺乳婴儿的影响：截至修订日期，没有找到相关的已发布信息。 ◉ 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:No information is available on the use of articaine during breastfeeding. Based on the low excretion of other local anesthetics into breastmilk, a single dose of articaine injected during breastfeeding is unlikely to adversely affect the breastfed infant. However, an alternate drug may be preferred, especially while nursing a newborn or preterm infant. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ 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

• WGK Germany：
  3
• 储存条件：
  2-8°C，惰性气体

制备方法与用途

阿替卡因（Hoe-045游离碱）是一种含有酯基的酰胺类麻醉剂，能与神经内腔内的电压门控钠通道α亚单位可逆结合，有效缓解疼痛。研究显示，阿替卡因还能通过抑制NF-κB激活和NLRP3炎症途径改善LPS诱导的急性肾损伤。

反应信息

• 作为反应物：
  描述：

  阿替卡因 在 氯化亚砜 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 Articaine acid propionamide
  参考文献：
  名称：

  10.14233/ajchem.2024.31509

  摘要：

  The present study reveals 4-methyl-3-(propylamino)thiophene-2-carboxylic acid (Articaine acid) as precursor derivative to synthesize novel thiophene compounds to evaluate their biological activity. The synthesized compounds were subjected to comprehensive characterization techniques including mass spectra, NMR and IR spectroscopy, confirming their structural integrity. Their antimicrobial activity was assessed via minimum inhibitory concentration (MIC) assay against selected bacterial strains. The results emphasize the potential therapeutic applications of these thiophene analogues as efficacious antimicrobial agents, thereby encouraging further investigation. Molecular docking was used to examine thiophene derivative binding affinities on the S. aureus tyrosyl-tRNA synthetase protein and it was found that phenylethylamine derivatives had the highest binding affinity, followed by cyclohexyl methyl and benzylamine derivatives.

  DOI：

  10.14233/ajchem.2024.31509
• 作为产物：
  描述：

  methyl 3-methyl-1-oxo-4-[2-(propylamino)propanoylamino]-2,3-dihydrothiophene-5-carboxylate 生成 阿替卡因
  参考文献：
  名称：

  RIPPEL, ROBERT;FLEMMING, HANS-WOLFRAM;RUKWIED, MANFRED

  摘要：

  DOI：

文献信息

• [EN] THERAPEUTIC ACRYLATES AS ENHANCED MEDICAL ADHESIVES<br/>[FR] ACRYLATES THÉRAPEUTIQUES UTILES EN TANT QU'ADHÉSIFS MÉDICAUX AMÉLIORÉS
  申请人：UNIV CARNEGIE MELLON

  公开号：WO2018052936A1

  公开（公告）日：2018-03-22

  Provided herein are therapeutic acrylate compounds useful as medical adhesives, comprising a therapeutic agent covalently linked to a methacrylate or cyanoacrylate moiety. Adhesive compositions and kits, such as liquid sutures and bone cement also are provided along with uses for the compositions.

  本文提供了作为医用粘合剂有用的治疗丙烯酸酯化合物，包括与甲基丙烯酸酯或氰丙烯酸酯基团共价连接的治疗剂。此外还提供了粘合剂组合物和套件，如液体缝合线和骨水泥，以及这些组合物的用途。
• TREPROSTINIL PRODRUGS
  申请人：United Therapeutics Corporation

  公开号：US20210054009A1

  公开（公告）日：2021-02-25

  Provided are novel prodrugs of treprostinil, as well as methods of making and methods of using these prodrugs.

  提供了特瑞普罗斯汀的新型前药，以及制备这些前药的方法和使用这些前药的方法。
• [EN] PRODRUGS OF SECONDARY AMINE COMPOUNDS<br/>[FR] PROMÉDICAMENTS DE COMPOSÉS AMINE SECONDAIRES
  申请人：ALKERMES PHARMA IRELAND LTD

  公开号：WO2013088255A1

  公开（公告）日：2013-06-20

  The present invention relates to compounds of Formula (I).

  本发明涉及式(I)的化合物。
• PHOSPHONIUM ION CHANNEL BLOCKERS AND METHODS FOR USE
  申请人：Nocion Therapeutics, Inc.

  公开号：US20210128589A1

  公开（公告）日：2021-05-06

  The invention provides compounds of Formula (I), or pharmaceutically acceptable salts thereof: The compounds, compositions, methods and kits of the invention are useful for the treatment of pain, itch, and neurogenic inflammation.

  本发明提供了式(I)的化合物，或其药用可接受的盐： 本发明的化合物、组合物、方法和试剂盒可用于治疗疼痛、瘙痒和神经性炎症。
• SUGAR CHAIN-ATTACHED LINKER, COMPOUND CONTAINING SUGAR CHAIN-ATTACHED LINKER AND PHYSIOLOGICALLY ACTIVE SUBSTANCE OR SALT THEREOF, AND METHOD FOR PRODUCING SAME
  申请人：GLYTECH INC.

  公开号：US20150306235A1

  公开（公告）日：2015-10-29

  To provide a carrier linker that is capable of improving the water solubility of a physiologically active substance and more quickly releasing the physiologically active substance under specific conditions without utilizing light or enzymatic cleavage. [Solution]A novel sugar chain-attached linker comprising a sugar chain that is attached as a carrier.

  提供一种载体连接剂，能够提高生理活性物质的水溶性，并在特定条件下更快地释放生理活性物质，而无需利用光或酶解。【解决方案】一种新型的糖链连接剂，包括作为载体附着的糖链。