captopril

• 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: captopril
• 英文别名: DL-captopril；1-(2-methyl-3-sulfaniumylpropanoyl)pyrrolidine-2-carboxylate
• 化学式: C₉H₁₅NO₃S
• mdl: MFCD00168073
• 分子量: 217.289
• InChiKey: FAKRSMQSSFJEIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

毒理性

• 在妊娠和哺乳期间的影响

使用哺乳期的总结：由于母乳中卡托普利的含量较低，婴儿摄入的量很小，预计不会对哺乳婴儿造成任何不良影响。 对哺乳婴儿的影响：在一项报告中，12位母亲中有几位在每天三次服用卡托普利100毫克的同时继续哺乳。婴儿中没有看到不良影响。[1] 一名妇女在怀孕期间被诊断为库欣病。产后，她每天三次服用美替拉酮250毫克，每天两次服用比索洛尔10毫克和卡托普利12.5毫克。她用大约50%的牛奶和50%的配方奶喂养她的早产儿。在产后5周，婴儿的儿科团队发现他的生长和发育是适当的。[3] 对泌乳和母乳的影响：在一篇论文中报告的一系列对照研究中，卡托普利对泌乳素分泌肿瘤患者的泌乳素昼夜节律、对泌乳素刺激药物的响应或血清泌乳素没有影响。[4] 在一项对年轻高血压男性的研究中，口服卡托普利25毫克在剂量后90分钟显著降低了血清泌乳素，与安慰剂相比。[5] 在已经建立泌乳的母亲中，母体泌乳素水平可能不会影响她的哺乳能力。 在一项报告中，12名受试者中有1名妇女在每天三次服用卡托普利100毫克时无法产生足够的乳汁进行研究，尽管她已经成功哺乳了6个月。[1] 目前尚不清楚这种减少是否是卡托普利的效果。

◉ Summary of Use during Lactation:Because of the low levels of captopril in breastmilk, amounts ingested by the infant are small and would not be expected to cause any adverse effects in breastfed infants. ◉ Effects in Breastfed Infants:In one report of 12 mothers, several continued to breastfeed their infants while taking captopril 100 mg three times daily. No adverse effects were seen in the infants.[1] A woman was diagnosed with Cushing's disease during pregnancy. Postpartum she took metyrapone 250 mg 3 times daily, bisoprolol 10 mg twice daily, and captopril 12.5 mg twice daily. She breastfed her preterm infant about 50% milk and 50% formula. At 5 weeks postpartum, the infant's pediatric team found his growth and development to be appropriate.[3] ◉ Effects on Lactation and Breastmilk:In a series of controlled studies reported in one paper, captopril had no effect on the circadian rhythm of prolactin, the response to prolactin-stimulating drugs or serum prolactin in patients with prolactin-secreting tumors.[4] In a study of young hypertensive males, captopril 25 mg orally markedly decreased serum prolactin at 90 minutes after the dose compared to placebo.[5] The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed. In one report, 1 woman out of 12 subjects was unable to produce enough milk for the study while taking captopril 100 mg 3 times daily even though she had been successfully breastfeeding for 6 months.[1] It is not known if this decrease was an effect of captopril.

来源:Drugs and Lactation Database (LactMed)

反应信息

• 作为反应物：
  描述：

  captopril 在 碘 作用下， 以 水 为溶剂， 生成 captopril disulfide
  参考文献：
  名称：

  Mixed disulfides

  摘要：

  本发明涉及公式##STR1##中的化合物，其中A和A.sub.1是氨基酸残基，X是α-亚氨基酸残基，R.sub.1是氢，低烷基或卤代低烷基。这些化合物可用作降压剂。

  公开号：

  US04284624A1
• 作为产物：
  描述：

  N-(3-chloro-2-D-methylpropanoyl)-L-proline 生成 captopril
  参考文献：
  名称：

  Process for preparation of optically active N-mercaptoalkanoylamino acids

  摘要：

  本发明揭示了一种制备光学活性N-巯基烷酰氨基酸的方法，包括：（1）将光学活性β-羟基烷酸与卤代试剂反应，制备光学活性β-卤代烷酰卤（2）将β-卤代烷酰卤与氨基酸反应，产生光学活性N-β-卤代烷酰氨基酸，（3）将N-β-卤代烷酰氨基酸与能够将卤素转化为巯基团的试剂反应，其中在整个制备过程中，公式（II）、（III）、（IV）、（V）和（VI）的构型在所有光学活性化合物中保持不变，以制备公式（I）所代表的化合物。本发明的产品，例如N-(3-巯基-2-D-甲基丙酰基)-L-脯氨酸，抑制血管紧张素I向血管紧张素II的酶促转化，因此有助于缓解与血管紧张素相关的高血压。

  公开号：

  US04371699A1

文献信息

• Process for the preparation of a pharmacologically active chemical combination
  申请人：Laboratori Alchemica S.r.l.

  公开号：US06369260B1

  公开（公告）日：2002-04-09

  Process for the preparation of a pharmacologically active chemical combination constituted by the association, through chemical bonds, of units equal to one another, having each an own pharmacological activity, and with the general formula (I): M—A—X—B—M, where M indicates said unit having an own pharmacological activity, X indicates a “bidentate” structure suitable to interconnect the M units, A and B indicate functional groups either equal to or different from one another which allow the interconnection between M and X.

  制备一种药物活性化学组合物的过程，该组合物通过化学键连接相等单元构成，每个单元均具有自身的药理活性，并具有通用公式(I)：M—A—X—B—M，其中M表示具有自身药理活性的单元，X表示适合于相互连接M单元的“双齿”结构，A和B表示相等或不同的功能团，它们允许M和X之间的相互连接。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UNIV OSLO

  公开号：WO2018033719A1

  公开（公告）日：2018-02-22

  The invention provides compounds for use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal, said method comprising administration of said compound in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic, wherein said compound has the general formula I: (I) (wherein: Q is a lipophilic, zinc chelating moiety which is selective for Zn2+ ions and which comprises at least one, preferably two or more (e.g 2, 3 or 4), optionally substituted, unsaturated heterocyclic rings, e.g. 5 or 6-membered heterocyclic rings (such rings preferably include at least one heteroatom selected from N, S and O, preferably N); wherein any optional substituents may be selected from C1-6 alkyl, C1-6 alkoxy, halogen, nitro, cyano, amine, and substituted amine; each L, which may be the same or different, is a covalent bond or a linker; each W, which may be the same or different, is a non-peptidic hydrophilic group which comprises one or more hydroxy groups; and x is an integer from 1 to 3) or a stereoisomer, pharmaceutically acceptable salt or prodrug thereof.

  该发明提供了一种化合物，用于治疗和/或预防人类或非人哺乳动物体内的细菌感染，所述方法包括将该化合物与β-内酰胺类抗生素（可以同时、分开或顺序地）结合给药，其中所述化合物具有一般式I：（I）（其中：Q是一个亲脂性、选择性结合Zn2+离子的基团，包括至少一个，最好是两个或更多（例如2、3或4个），可选择地取代的不饱和杂环环，例如5或6元杂环环（这些环最好包括至少一个从N、S和O中选择的杂原子，最好是N）；其中任何可选择的取代基可以选择自C1-6烷基、C1-6烷氧基、卤素、硝基、氰基、胺和取代胺；每个L，可以相同也可以不同，是一个共价键或一个连接基；每个W，可以相同也可以不同，是一个非肽性亲水基团，包括一个或多个羟基；x是1到3之间的整数）或其立体异构体、药学上可接受的盐或前药。
• 1H, 13C NMR and UV spectroscopy studies of gold(III)-tetracyanide complex with l-cysteine, glutathione, captopril, l-methionine and dl-seleno-methionine in aqueous solution
  作者：Bassem A. Al-Maythalony、Mohamed I.M. Wazeer、Anvarhusein A. Isab

  DOI：10.1016/j.ica.2010.06.001

  日期：2010.10

  with biologically important thiols, thioether and selenoether were carried out and monitored using 1H, 13C NMR and UV spectroscopy. These ligands include l-cysteine, glutathione, captopril, l-methionine and dl-seleno-methionine. Thiols show very strong affinity to be oxidized into the disulfide by auricyanide, which gets reduced to aurocyanide [Au(CN)2]−. l-cysteine reaction mechanism with [Au(CN)4]−

  使用1 H，13 C NMR和UV光谱法进行并监测了Auricyanide [Au（CN）4 ] -与生物学上重要的硫醇，硫醚和硒醚的相互作用。这些配体包括l-半胱氨酸，谷胱甘肽，卡托普利，l-蛋氨酸和dl-硒代蛋氨酸。硫醇显示出很强的亲和力，可被金硫氰酸盐氧化为二硫键，而被还原为金硫氰酸盐[Au（CN）2 ] -。发现具有[Au（CN）4 ] -的l-半胱氨酸反应机理取决于反应物的摩尔比。虽然L-蛋氨酸对金刚烷胺完全呈惰性，但dl-Se-蛋氨酸与[Au（CN）4 ]具有一定的反应性。−将溶液的pH升高至12以利于氰化物交换之后。
• COMPOSITIONS AND METHODS FOR CYTOPROTECTION
  申请人：Basnakian Alexei G.

  公开号：US20090042850A1

  公开（公告）日：2009-02-12

  The present invention provides compositions and methods for cytoprotection. In particular, it provides zinc chelate compositions comprising at least one zinc ion and at least one aminothiol ligand.

  本发明提供了细胞保护的组合物和方法。特别是，它提供了包含至少一个锌离子和至少一个氨硫醇配体的锌螯合物组合物。
• D-proline derivatives
  申请人：——

  公开号：US20030100770A1

  公开（公告）日：2003-05-29

  New compounds have the formula: 1 wherein R, R 1 , X and Y have the meanings described herein. Methods are set forth for synthesizing these compounds and using these compounds to treat diseases associated with amyloidosis, such as Alzheimer's disease, maturity onset diabetes mellitus, familial amyloid polyneuropathy, scrapie, and Kreuzfeld-Jacob disease.

  新化合物的化学式为：1，其中R、R1、X和Y的含义如下所述。本发明还公开了合成这些化合物的方法以及使用这些化合物治疗与淀粉样变性相关的疾病，例如阿尔茨海默病、成年发病型糖尿病、家族性淀粉样多神经病、病毒性脑炎和克雅氏病的方法。