2 Chapter II Anesthetics 2016 9 813 Ge
- Slides: 71
第 2章 麻醉药 Chapter II Anesthetics 2016, 9, 8~13 Ge Meng
Introduction Past Present
Section I. Local Anesthetics 1. 1 局麻药的发展:结构改造 Structure Modification
From discovery of procaine to classification of local anesthetics Cocaine 1884 Tropacocaine Othoform etc Procaine 1904 Water soluble No side effects 对氨基苯甲酸酯 芳酸酯类 盐酸丁卡因 酰胺类 利多卡因 氨基酮类 布比卡因 达克罗宁 法立卡因 氨基醚类 氨基甲酸酯类 奎尼卡因 地哌冬
二、局麻药化学结构类型 1. 2 Structure Type of Local Anethetics 1. 2. 1芳酸酯类 Aromatic acid esters TD: 盐酸普鲁卡因、盐酸丁卡因、等。 Ester, hydrolysis, unstable, moderate active. 活性指数为 1 More penetrable, more active and toxic. 活性指数为 10 浸润麻醉和眼角膜表面麻醉
1. 2 Structure Type of LA 1. 2. 1 Aromatic acid ester
1. 2 Structure types of LA 1. 2. 2 酰胺类 Amides TD:利多卡因 More active,double active time,more pemetrable and diffusive,antiarrythmia
1. 2 Structure type of LA 1. 2. 2 Amides Other drugs:丙胺卡因, 甲哌卡因, 布比卡因, 罗哌卡因
1. 2 Structure Type of LA 1. 2. 3 氨基酮类 Amino ketones -CH 2 - ~ -OTD: 1. 达克罗宁 Dyclonine 临床常用 2. 法立卡因 Falicaine more active and penetrable, 速效持久,表面麻醉
1. 2 Structure Type of LA 1. 2. 4 氨基醚类 Amino ethers -O- ~ -COO- or –CONHTD: 奎尼卡因 Quinisocaine (二甲异喹, Dimethisoquin) About 1000 times potential as lidocaine. 普莫卡因 Promocaine Strong and long-time effect. Both are much more stable than ever, Why?
1. 2 Structure Type of LA 1. 2. 5 氨基甲酸酯类 Amino carbamates Ester - NH 2 - Benzene TD: 地哌冬Diperodon (迪奥散, Diothane) 庚卡因 Heptacaine
[Typical Drug]普鲁卡因 (Procaine) 【Name】 4 -氨基苯甲酸-2 -(二乙氨基)乙酯; 4 -amino-benzoic acid-2 -(diethylamino)ethyl ester; 【Allias】奴佛卡因 (Novocaine); 【Clinical】盐酸普鲁卡因; 【Usages】外科小手术。
Discovery Cocaine β-Eucaine Tropacocaine Benzocaine
Novocaine SPR
Property v 1)Hydrolysis of ester PABA DEAE k T, p. H: p. H 3~ 3. 5 stable. This reaction could be accelerated under the basic, neutral and acid condition. v. Metabolites: PABA and DEAE.
Property 2) Identification of aromatic primary amine 重氮化 red azo dye 偶合 3) Oxydation of amino group turning into dark p. H 、T 、UV、O 2、M+
Retro-synthesis of Procaine 硝基卡因 Retro-synthesis Tree
【Synthetic Route】
Retro-synthesis of Lidocaine
Synthetic Route
第二节 全身麻醉药 Section II General Anesthetics 全麻药 根据给药途径不同 Classification 吸入麻醉药 Inhalation Anesthetics 静脉麻醉药 Intravenous Anesthetics 挥发性麻醉药 Volatile Anesthetics 不具有挥发性 Involatile
Chemical Structures of GA 药物的中英文名称对照 氧化亚氮(Nitrous Oxide);麻醉乙醚(Anesthetic Ether), 氟烷(Halothane, Fluothane);甲氧氟烷(Methoxyflurane), 恩氟烷(Enflurane);异氟烷(Isoflurane), 七氟烷(Sevoflurane);地氟烷(Desflurane)等。
Properties Physical properties: Opaque clear liquid, not inflammable, not explosive,very soluble in water。 Chemical properties: 1 Very stable under UV, strong base and other harsh conditions. 2 After decomposed by organic methods, Fcould be detected by its speciality.
Chemical Structures of Some Drugs 药物名称的中英文对照 硫喷妥钠(Thiopental Sodium); 海索比妥钠(Hexobarbital sodium); 氯胺酮(Ketamine); 羟丁酸钠(Sodium Hydroxybutyrate),又称:γ-羟丁酸钠。
Review Anethetics-2016 -09 -12 v LA and GA v TD|:Procaine,Lidocaine, Ketamine; v SAR of LA: 3 main parts (hydrophilic ability / lipophilic ability); v Structure nonspecific drug。
Retro-synthesis of Ketamine
Synthesis Route of Ketamine Mechanism ?
Rearrangement
Rearrangement Analysis
Please find the chiral center in ketemine! v v v Analgesic activity of (S)-(+) isomer is 3 times as its (R)-(-)isomer; Hypnotic activity of (S)-(+) isomer is 1. 5 times as its (R)-(-)isomer; Anesthetic activity of (S)-(+) isomer is 3. 4 times as its (R)-(-)isomer; Ilussion side effect of (S)-(+) isomer is less than its (R)-(-)isomer; Therefore:右旋体优于左旋体。
依托咪酯 Etomidate 【理化性质】 1、 白色结晶性粉末;rigid skeleton 2 、不溶于水,溶于乙醇;hydrophobic group 3、 具旋光性,药用R(+);chiral center 4、 酯基水解性,苄基咪唑甲酸衍生物和乙醇。Ester bond 【代谢】 Etomidate could be hydrolyzed into Et. OH and benzyl imidazole acid derivatives,which could be discharged by urine。
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