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Chapter 2 Sedative-hypnotics, antiepileptics and antipsychotics

Chapter 2 Sedative-hypnotics, antiepileptics and antipsychotics. Sedative-hypnotics: barbiturates, benzodiazepines Antiepileptics :glycolylureas, benzodiazepines, tricycles Antipsychotics and antidepressant: tricycles. 2.1 Acylureas

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Chapter 2 Sedative-hypnotics, antiepileptics and antipsychotics

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  1. Chapter 2 Sedative-hypnotics, antiepileptics and antipsychotics

  2. Sedative-hypnotics: barbiturates, benzodiazepines Antiepileptics :glycolylureas, benzodiazepines, tricycles Antipsychotics and antidepressant: tricycles

  3. 2.1 Acylureas Malonylureas and glycolylureas 2.1.1 Barbiturates---malonylureas （1）Structures

  4. （2）Structure-activity relationship non-srtucture specific drugs ---Pka ---P ---Metablism （3）Chemical and physical properties 1．Weak acid 2．Hydrosis 3．Reaction with AgNO3 4．Reaction with Pyridine and CuSO4

  5. (4) General synthesis of barbiturates

  6. (5) phenobarbital Name: Luminal Systematic name: 5-ethyl-5-phenyl-2,4,6-(1H,3H,5H)- pyrimidinetrione

  7. 2.1.2 glycolylureas

  8. Phenyltoin sodium Synonyme: dilantin sodium Systematic name: sodium 5,5-diphenyl-2,4- imidazolidinedione

  9. Synthesis of dilantin sodium:

  10. Physicochemical properties: • Hydrolysis • Weak acid • Reaction with AgNO3 • Reaction with pyridine and CuSO4 (blue) • Usage: antiepileptics

  11. 2.2 Benzodiazepine: the second generation sedative-hypnotics, almost replaced barbiturates. R1 R2 R3 R4 a CH3 H H Cl b CH3 H F Cl c H H H NO2 d H H Cl NO2 • diazepam, valium b.flutoprazepam c. nitrazepam • d. clonazepam

  12. Modicication:estazolam, alprazolam, trizolam and midazolam R1 R2 estazolam H H alprazolam CH3 H trizoalm CH3 Cl

  13. Structure- activity relationship: • Basic structure: 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one • The electron attractive substituents on ring A enforce the activity • NO2>Br>CF3>Cl • (3) Ring B is necessary for activity • (4) The electron attractive substituents with small volum on benzene • ring of C-5 will enforce the activity • (5) The hydrolysis of amide and imine

  14. diazepam （1）molecular structure 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (2）phycochemical properties （3）usage （4）storage

  15. 2.3 Tricycles 2.3.1 tricycles for antipsychotics Phenothiazines Thioxanthene Dibenzodiazepines

  16. 2.3.1 phenothiazines Structure-activity relationship: Phycochemical properties: oxidation

  17. Chlorpromazine hydrochloride 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine hydrochloride

  18. （1）properties and identification oxidation identicication a. reaction with HNO3 (red)，then light yellow b. reaction with FeCl3 (red) (2) storage：with antioxidant such as 连二亚硫酸钠、亚硫酸氢钠 or 维生素Ｃ。 （2）usage: antipsychotics

  19. 2.3.2 Thioxanthene

  20. 2.3.3 Dibenzodiazepines clozapine clothiapine

  21. 2.3.2 Tricycles for antidepressant R1 R2 H (CH2)3N(CH3)2 imipramine H (CH2)3NHCH3 desipramine Cl (CH2)3N(CH3)2 clomipramine

  22. Amitriptyline Nortriptyline

  23. 2.3.3 Tricycles for antiepileptics Carbamazepine Oxcarbazepine

  24. 2.4 butyrophenones haloperidol

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