Thiamine Derivatives of Disulfide Type. VIII. The Exchange Reaction between Thiamine Propyl Disulfide and the Various Thiols

スポンサーリンク

概要

• 論文の詳細を見る

• The exchange reactions between TPD and polyfunctional thiols such as glutathione, 2-aminoethylmercaptan, 2-hydroxyethylmercaptan and 2-carboxyethylmercaptan were examined under an anaerobic condition. The following conclusions were drawn from the results presented. From an analysis of the pH-rate profile of the reactions between TPD and thiols containing the amino group in a molecule, the reaction was revealed as the combination of the following three reactions through the pH range of 3 to 12,HB_1SSPr + NH_3^+RS^-→HB_1S^- + NH_3^+RSSPr B_1SSPr + NH_3^+RS^-→B_1S^- + NH_3^+RSSPr B_1SSPr + NH_2RS^-→B_1S^- + NH_2RSSPr where HB_1SSPr is the protonated form of TPD, NH_3^+RS^- is the protonated amino-thiol anion, HB_1S^- is the protonated thiamine and NH_3^+RSSPr is the protonated amino-alkyl propyl disulfide. On the other hand, in the reaction between TPD and thiol, 2-hydroxyethylmercaptan, the following two reaction equations were presented through the experimental pH range of 3.5 to 12.0. HB_1SSPr + RS^-→HB_1S + RSSPr B_1SSPr + RS^-→B_1S + RSSPr The second order rate constants of individual reactions were determined. The activation energies of these reactions obtained were about 10 kcal mole^<-1>, and the values of activation entropies were 5 to 24 cal mole^<-1> deg^<-1>. These second order rate constants were correlated with the pK_a values of the thiol group with Bronsted equation, log k=αpK_a + C, with a resultant very large α value. From this relationship, it may be concluded that these thiols are an extremely good nucleophile to the disulfide bond and especially to protonated TPD.

• 公益社団法人日本薬学会の論文
• 1969-08-25

著者

• 長谷川 淳

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 野上 寿

  東京大学薬学部

• 竹内 嘉智子

  グレラン製薬株式会社研究部

• 五十里 紀子

  グレラン製薬株式会社研究部

• 竹内 嘉智子

  Grelan Pharmaceutical Co., Ltd.

関連論文

• 粉体の物性に関する製剤学的研究(第2報) : 変速回転円筒内の粉体と液体の挙動比較
• インドメサシンの生物薬剤学的研究(第1報) : 家兎における, 静脈内投与時の血漿中濃度の解析, および十二指腸内投与時の剤形と吸収の関連性について
• Studies on the Syntheses of Heterocyclic Compounds. CXCV. The Structure of a Yellow Substance formed by Mild Oxidation of Aminopyrine.
• Pharmacokinetic Studies of Biliary Excretion. IV. The Relationship between the Biliary Excretion Behavior and the Elimination from Plasma of Azo Dyes and Triphenylmethane Dyes in Rat
• インドメサシンの生物薬剤学的研究(第2報) : ラット小腸管吸収機構およびヒト経口投与時における微粉化製剤の利用率
• Pharmacokinetic Studies of Biliary Excretion. I. Comparison of the Excretion Behavior in Azo Dyes and Indigo Carmine
• 医薬品の分解とその安定化(第8報)ノルフェニレフリンと糖類分解物との反応成績体
• 医薬品の分解と安定化(第7報)Norphenylephrineの水溶液中の安定性
• Studies on Absorption and Excretion of Drugs. V. On the Mechanism of Penetration of Sulfisomezole through the Intestinal Barrier in vitro
• Studies on Absorption and Excretion of Drugs. III. Kinetics of Penetration of Sulfonamides through the Intestinal Barrier in Vitro.
• 薬学を支えた薬科機器
• Studies on Absorption and Excretion of Drugs. VI. Effects of Cations and 2,4-Dinitrophenol on the Transport of Sulfonamides through the Small Intestine of Rat
• 非水溶液における呈色反応(第4報) : Bromophenol Blue とジメチルアミン誘導体の反応における置換基効果
• Thiamine Derivatives of Disulfide Type. IX. Exchange Reactions between Symmetrical Disulfide and L-Cysteine
• Disulfide形Thiamine誘導体(第10報) : Disulfide形ThiazoliumとL-Cysteineの交換反応
• 薬物相互作用に関するPharmacokinetics : 血漿中のChlorzoxazoneの濃度変化におよぼすZoxazolamineの影響
• 医薬品の分解とその安定化(第9報)アミノアルキルエステルの安定性におよぼす添加物の影響
• ラットにおけるスルピリンの吸収, 代謝, 排泄におよぼす投与経路の影響について
• ラットにおけるスルピリンの投与量の代謝, 排泄速度におよぼす影響について
• ラットにおけるスルピリンの代謝および排泄の速度論
• Pharmacokinetic Aspects of Elimination from Plasma and Distribution to Brain and Liver of Barbiturates in Rat
• Thiamine Derivatives of Disulfide Type. XIV. Kinetic Studies on the Reaction between Thiamine and Propyl Propane-Thiolsulfinate or -Thiolsulfonate
• スルピリンの吸収, 代謝, 排泄に関する速度論的研究 : 静注後のラット尿中代謝物の動態
• スルピリンの吸収, 代謝, 排泄に関する速度論的研究 (II) : 筋肉および経口投与後のラット尿中代謝物の動態
• スルピリンの吸収, 代謝, 排泄に関する速度論的研究 (I) : 静注後のラット尿中代謝物の動態
• Pharmacokinetics of Thiamine Derivatives. II. Elimination of Thiamine Derivatives from the Blood of Rat
• 医薬品の分解とその安定化(第4報) : アミノアルキルエステルの構造と安定性について その2
• 医薬品の分解とその安定化(第3報) : アミノアルキルエステルの構造と安定性について その1
• 医薬品の分解とその安定化(第2報) : 2-Diethylaminoethyl 3-Methyl-2-phenylvalerate HydrochlorideおよびMethobromideの水溶液中の安定性
• Pharmacokinetics of Thiamine Derivatives. I. Formation of Thiamine from Thiamine Propyl Disulfide by Erythrocytes of Rat
• Thiamine Derivatives of Disulfide Type. VIII. The Exchange Reaction between Thiamine Propyl Disulfide and the Various Thiols
• Thiamine Derivatives of Disulfide Type. V. Kinetic Studies of the Reaction between Thiamine Propyl Disulfide or Homologes and L-Cysteine
• Thiamine Derivatives of Disulfide Type. IV. The Exchange Reaction between Thiamine Propyl Disulfide and L-Cysteine
• Thiamine Derivatives of Disulfide Type. III. Enzyme Systems in Rat Intestine contributed for Thiamine Formation from the Disulfide Type Derivatives
• Thiamine Derivatives of Disulfide Type. II. The Formation of Thiamine from the Disulfide Derivatives in Rat Intestine in Vitro
• Thiamine Derivatives of Disulfide Type. I. Formation of Thiamine from Thiamine Propyl Disulfide in Rat Intestine in Vitro
• Studies on Decomposition and Stabilization of Drugs in Solution. XVIII. The Hydrolysis of Phthalylsulfathiazole
• Thiamine Derivatives of Disulfide Type. XV. The Ring Opening-closing Reactions of 4-Methylthiazolium Salts
• Thiamine Derivatives of Disulfide Type. XI. Oxidation of Dipropyl Disulfide with Hydrogen Peroxide and Properties of the Products
• Thiamine Derivatives of Disulfide Type. XIII. Kinetic Studies on the Degradation of Propyl Propanethiolsulfonate by Hydroxyl Ion
• Thiamine Derivatives of Disulfide Type. XII. Kinetic Studies on the Reaction between Propyl Propane-Thiolsulfinate or -Thiolsulfonate and Cysteine
• The Stabilization Mechanism of Acylcholinesters in Aqueous Solution by Sodium Lauryl Sulfate
• Studies on Absorption and Excretion of Drug. XIII. The Sorption of Surface Active Agents into the Intestinal Tissue of Rat and Their Effect on the Drug Absorption in Vitro
• Studies on Powdered Preparations. IX. Thermal Analysis of the Velocity of Reaction between Dried Aluminum Hydroxide Gel and Acid.
• Thiamine Derivatives of Disulfide Type. VII. Kinetics between Thiamine Tetrahydrofurfuryl Disulfide and L-Cysteine or Its Derivatives
• 薬物の吸収ならびに排泄に関する研究(第12報) : サルファ剤の尿排泄に関する速度論的研究
• Thiamine Derivatives of Disulfide Type. VI. Kinetic Studies of the Thiol-Exchange Reaction between Thiamine Disulfide and L-Cysteine
• Studies on Powdered Preparations. XX. Disintegration of the Aspirin Tablets containing Starches as Disintegrating Agent
• Studies on Powdered Preparations. III. Studies on Disintegration of Basic Magnesium Carbonate Tablet.
• Studies on Powdered Preparations. II. Studies on Tablet Disintegration of Calcium Carbonate by Thermal Analysis.
• Studies on Decomposition and Stabilization of Drugs in Solution. I. Chemical Kinetic Studies on Aqueous Solution of Phenobarbital.
• Pharmacokinetic Analysis on the Disappearance of Ethoxybenzamide from Plasma. Statistical Treatment of Data of Two Compartmental Model by a Digital Computer
• 薬物の吸収ならびに排泄に関する研究(第16報) : ラット尿中のスルピリンならびにその代謝物の定量法
• Studies on Absorption and Excretion of Drugs. XI. Relation between Chemical Structure and Absorption Rate. (3). Intramolecular Interaction Constant, Additivity Rule and Prediction for Intestinal Absorption Rate Coefficient
• Studies on Absorption and Excretion of Drugs. X. Relation between Chemical Structure and Absorption Rate. (2). Substituent Constant for Absorption Rate Coefficient of Foreign Organic Compounds
• Studies on Absorption and Excretion of Drugs. IX. Relation between Chemical Structure and Absorption Rate. (1). Effects of the Number and the Position of OH-Groups on the Intestinal Absorption Rate of Benzoyl Derivatives
• Studies on Absorption and Excretion of Drug. VIII. The Release Rate in vivo of Antipyretic and Analgesic Drugs from Commercial Sugar Coated Tablets.
• Studies on Absorption and Excretion of Drugs. IV. Absorption of Various Sulfonamides from the Rat Small Intestine by the Perfusion Method in vivo.
• Studies on Percutaneous Absorption. II. Effect of the Incorporated Substance.
• 軟膏の研究(第1報)軟膏の経皮吸収の新測定法について
• Studies on Tablets. V. Static Electrification in Tablet Compression.
• Studies on Tablets. IV. Frictional Electrification of Crystalline Medicines.
• The Change of Particle Size in an Aqueous Suspension.

もっと見る 閉じる

スポンサーリンク