‫ﺍﶈﺎﺿﺮﺓ ﺍﻟﺜﺎﻧﻴﺔ‬ ‫ﺍﻟﻜﻴﻤﻴﺎﺀ ﺍﻟﺼﻴﺪﻟﻴﺔ ‪٢‬‬

‫ﻣﻀﺎدات اﻟﺬھﺎن‬
‫‪Antipsychotic Drugs‬‬

‫‪ -‬ﻣﻔﻬﻮم اﻟﺬﻫﺎن‪:‬‬
‫ﺍﻟﺬﻫﺎﻥ ﺣﺎﻟﺔ ﻣﺮﺿﻴﺔ ﺗﺼﻴﺐ ﺍﻟﻜﻴﺎﻥ ﺍﻟﻨﻔﺴﻲ ﻭﺍﻟﻌﻘﻠﻲ ﻭﺗﺘﻤﻴﺰ ﻫﺬﻩ ﺍﳊﺎﻟﺔ )ﺧﺎﺻﺔﹰ ﺍﻟﻔﺼﺎﻡ ﻭﻫﻮ ﺃﺧﻄﺮﻫﺎ( ﺑﺄﻥ ﺍﳌﺮﻳﺾ ﻳﻨﻔﺼﻞ‬
‫ﻋﻦ ﺍﻟﻌﺎﱂ ﻭﻳﻌﻴﺶ ﰲ ﻋﺎﱂ ﺧﺎﺹ ﺑﻪ ﻣﻠﻲﺀ ﺑﺎﻷﻭﻫﺎﻡ ﻭﺍﻟﺘﺨﻴﻼﺕ ﻭﺍﻟﻮﺳﺎﻭﺱ ﻭﺍﳍﻠﻮﺳﺔ ﻣﺒﺘﻌﺪﺍﹰ ﻋﻦ ﺍﻟﻮﺍﻗﻊ ﻭﺗﻈﻬﺮ ﻟﺪﻳﻪ‬
‫ﺍﺿﻄﺮﺍﺑﺎﺕ ﻓﻜﺮﻳﺔ ﻭﺳﻠﻮﻛﻴﺔ ﻭﺍﻧﻔﻌﺎﻟﻴﺔ‪.‬‬

‫‪ -‬ﻣﻀﺎﺩﺍﺕ ﺍﻟﺬﻫﺎﻥ ﺗﺸﻤﻞ ﳎﻤﻮﻋﺔ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﱵ ﺗﺴﺘﺨﺪﻡ ﰲ ﻣﻌﺎﳉﺔ ﺍﻷﻣﺮﺍﺽ ﺍﶈﺪﺛﺔ ﻟﺸﺮﺥ ﻛﺒﲑ ﰲ ﺍﻟﻜﻴﺎﻥ ﺍﻟﻨﻔﺴﻲ‬
‫وﺗﺸﻤﻞ‪:‬‬
‫‪ .١‬ﺍﻟﻔﺼﺎﻡ )ﺍﻟﺸﻴﺰﻭﻓﺮﻳﻨﺎ( ﺑﺄﺷﻜﺎﻟﻪ ﺍﻟﺴﺮﻳﺮﻳﺔ ﺍﳌﺨﺘﻠﻔﺔ ﻭﺍﻟﺒﺴﻴﻄﺔ ﻭﺍﻟﺸﺪﻳﺪﺓ )ﻣﺜﻞ ﺍﳊﺎﻻﺕ ﺍﳉﻤﻮﺩﻳﺔ(‪.‬‬
‫‪ .٢‬ﺍﻟﺸﻴﺰﻭﻓﺮﻳﻨﻴﺎ ﺍﻟﺰﻭﺭﻳﺔ ‪) Paranoya‬ﺍﻟﺬﻫﺎﻥ ﺍﻟﻜﱪﻳﺎﺋﻲ ﺃﻭ ﺟﻨﻮﻥ ﺍﻟﻌﻈﻤﺔ(‪ ،‬ﻭﺍﳊﺎﻻﺕ ﻧﻈﲑﺓ ﺍﻟﺰﻭﺭﻳﺔ ‪.Paranoid Cases‬‬
‫‪ .٣‬ﺍﻹﺻﺎﺑﺔ ﺑﺎﳍﻮﺱ )ﺍﳉﻨﻮﻥ( ‪ Mania‬ﻭﻣﺎﲢﺖ ﺍﳍﻮﺱ )‪.(Hypomania‬‬
‫‪ .٤‬ﺣﺎﻻﺕ ﺍﻟﺴﻮﺩﺍﻭﻳﺔ‪.‬‬
‫ﻭﺑﻘﻴﺔ ﺍﳊﺎﻻﺕ ﺍﻟﱵ ﺗﺴﺒﺐ ﺷﺮﺧ‪‬ﺎ ﻭﺍﺳﻌ‪‬ﺎ ﰲ ﺍﻟﻜﻴﺎﻥ ﺍﻟﻨﻔﺴﻲ ﻣﺜﻞ ﺍﻻﻧﻄﻮﺍﺋﻴﺔ ﻭﺣﺎﻻﺕ ﺍﳌﺮﺍﻕ ﺍﻟﺘﺸﺎﺅﻣﻴﺔ‪.‬‬

‫‪Antipsychotic Drugs /Neuroleptics‬‬

‫‪ .١‬ﻣﺸﺘﻘﺎﺕ ﺍﻟﻔﻴﻨﻮﺛﻴﺎﺯﻳﻦ ‪Derivatives of Phenothiazine‬‬

‫‪ .٢‬ﻣﺸﺘﻘﺎﺕ ﺍﻟﺒﻴﻮﺗﲑﻭﻓﻴﻨﻮﻥ ‪Buterophenon Derivatives :‬‬
‫‪ .٣‬ﻣﺸﺘﻘﺎﺕ ﺛﻴﻮﻛﺰﺍﻧﺘﲔ ‪: Thioxanthenes‬‬
‫‪ .٤‬ﻛﻠﻮﺭﺑﺮﻭﺛﻴﻜﺴﲔ ‪Chlorprothexine .‬‬

‫‪٢٥‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 ‫‪ .٥‬ﺃﻣﻼﺡ ﺍﻟﻠﻴﺜﻴﻮﻡ ‪ :‬ﻭﳝﺜﻠﻬﺎ ‪:‬‬
‫• ﺳﻠﻔﺎﺕ ﺍﻟﻠﻴﺜﻴﻮﻡ ‪Lithium Sulfate .‬‬
‫• ﺳﺘﺮﺍﺕ ﺍﻟﻠﻴﺜﻴﻮﻡ ‪Lithium Citrate .‬‬
‫• ﻛﺮﺑﻮﻧﺎﺕ ﺍﻟﻠﻴﺜﻴﻮﻡ ‪Lithium Carbonate .‬‬

‫اﻟﻔﻴﻨﻮﺗﻴﺎزﻳﻨﺎت‬
‫‪PHENOTHIAZINES‬‬

‫اﻟﻔﻴﻨﻮﺛﻴﺎزﻳﻨﺎت‪ :‬ﻋﻼﻗﺔ اﻟﺒﻨﻴﺔ ﺑﺎﻟﺘﺄﺛﻴﺮ‬

‫‪Structure-Activity Relationships of PHENOTHIAZINES‬‬

‫‪ -‬ﻭﺟﻮﺩ ﳎﻤﻮﻋﺔ ﺳﺎﺣﺒﺔ ﻟﻼﻟﻜﺘﺮﻭﻧﺎﺕ ﰲ ﺍﳌﻮﻗﻊ ﺭﻗﻢ ‪ ٣‬ﻣﻦ ﻧﻮﺍﺓ ﺍﻟﻔﻴﻨﻮﺗﻴﺎﺯﻳﻦ ﻳﻌﻄﻲ ﻣﺮﻛﺒﺎﺕ ﺍﻛﺜﺮ ﻓﻌﺎﻟﻴﺔ ﻣﻦ ﺍﳌﺮﻛﺒﺎﺕ ﺍﻟﻐﲑ‬
‫ﻣﺴﺘﺒﺪﻟﺔ ﻭﻻ ﳛﺪﺙ ﻣﺜﻞ ﻫﺬﺍ ﰲ ﺣﺎﻟﺔ ﺍﳌﻮﻗﻊ ﺭﻗﻢ ‪) ٢‬ﺍﻟﻜﻠﻮﺭﺑﺮﻭﻣﺎﺯﻳﻦ( ‪.‬‬

‫‪ -‬ﺍﻻﺳﺘﺒﺪﺍﻝ ﰲ ﺍﳌﻮﻗﻊ ‪ ١‬ﺃﻭ ‪ ٤‬ﻳﻨﻘﺺ ﺍﻟﻔﻌﺎﻟﻴﺔ ﺍﳌﻀﺎﺩﺓ ﻟﻠﺬﻫﺎﻥ‪.‬‬

‫‪٢٦‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 ‫‪ -‬ﻭﺟﻮﺩ ‪ ٣‬ﻓﺤﻮﻡ ﺑﲔ ﺃﺯﻭﺕ ﺍﳊﻠﻘﺔ ﻭ ﺃﺯﻭﺕ ﺍﻟﺴﻠﺴﻠﺔ ﺿﺮﻭﺭﻱ ﻹﻋﻄﺎﺀ ﺍﻟﺘﺄﺛﲑ ﺍﳌﻀﺎﺩ ﻟﻠﺬﻫﺎﻥ‪.‬‬
‫‪ -‬ﳎﻤﻮﻋﺔ ﺍﻟﺪﻱ ﻣﻴﺘﻴﻞ ﺃﻣﲔ ﳑﻜﻦ ﺃﻥ ﺗﻜﻮﻥ ﰲ ﺳﻠﺴﻠﺔ ﺃﻟﻴﻔﺎﺗﻴﺔ ﺃﻭ ﻣﻮﺟﻮﺩﺓ ﰲ ﺣﻠﻘﺔ ﻏﲑ ﻣﺘﺠﺎﻧﺴﺔ ﻛﺎﻟﺒﻴﱪﺍﺯﻳﻦ ﺍﻭ‬
‫ﺍﻟﺒﻴﱪﻳﺪﻳﻦ‪.‬‬
‫‪ -‬ﻣﺸﺘﻘﺎﺕ ﺍﻟﺒﻴﱪﺍﺯﻳﻦ ﺗﻜﻮﻥ ﺃﻛﺜﺮ ﻓﻌﺎﻟﻴﺔ ﻭﺫﺍﺕ ﺍﻧﺘﻘﺎﺋﻴﺔ ﻓﺎﺭﻣﺎﻛﻮﻟﻮﺟﻴﺔ ﺃﻋﻠﻰ )ﻓﻠﻮﻓﻴﻨﺎﺯﻳﻦ( ﺣﻴﺚ ﺗﻌﻄﻲ ﺗﺄﺛﲑﺍﺕ ﻣﻀﺎﺩﺓ‬
‫ﻟﻠﺬﻫﺎﻥ ﻳﺘﻐﻠﺐ ﻓﻴﻬﺎ ﺍﻟﺘﺄﺛﲑ ﺍﳌﻀﺎﺩ ﻟﻠﺸﻌﻮﺭ ﺑﺎﻟﻘﻠﻖ ﻭﻛﺬﻟﻚ ﺗﻌﻄﻲ ﺗﺄﺛﲑ ﻗﻮﻱ ﻣﻀﺎﺩ ﻟﻠﻘﺊ ﺑﺎﻻﺿﺎﻓﺔ ﺍﱃ ﺃﻥ ﺍﻟﺘﺄﺛﲑﺍﺕ ﺍﳉﺎﻧﺒﻴﺔ‬
‫ﻛﺎﻟﻨﻌﺎﺱ ﻭﻫﺒﻮﻁ ﺍﻟﻀﻐﻂ ﺍﻟﱵ ﺗﺴﺒﺒﻬﺎ ﻣﺸﺘﻘﺎﺕ ﺍﻟﻔﻴﻨﻮﺗﻴﺎﺯﻳﻦ ﺑﺸﻜﻞ ﻋﺎﻡ ﺗﻜﻮﻥ ﰲ ﻣﺮﻛﺒﺎﺕ ﻫﺬﻩ ﺍﻟﺴﻠﺴﻠﺔ ﺧﻔﻴﻔﺔ‪.‬‬

‫‪ -‬ﻭﺟﻮﺩ ﳎﻤﻮﻋﺎﺕ ﻗﻄﺒﻴﺔ ﻣﺜﻞ ﺍﻟﻔﻴﻨﻴﻞ‪ ,‬ﺍﻟﺪﻱ ﻣﻴﺘﻴﻞ ﺃﻣﻴﻨﻮ‪ ,‬ﺍﳍﻴﺪﺭﻭﻛﺴﻴﻞ ﺗﻨﺘﺞ ﻓﻌﺎﻟﻴﺔ ﻣﻬﺪﺋﺔ ﺃﻗﻞ‪.‬‬
‫‪ -‬ﺍﻟﻔﻴﻨﻮﺗﻴﺎﺯﻳﻨﺎﺕ ﺗﺴﺒﺐ ﺍﻛﺘﺌﺎﺑﺎ ﺑﺪﺭﺟﺔ ﺃﻗﻞ ﻣﻦ ﺍﻟﺒﺎﺭﺑﻴﺘﻮﺭﺍﺕ ﻭﺍﻟﺒﱰﻭﺩﻳﺎﺯﻳﺒﻴﻨﺎﺕ‪.‬‬

‫ﻛﻠﻮرﺑﺮوﻣﺎزﻳﻦ ‪Chlorpromazine‬‬

‫‪2-chloro-10-[3-(-dimethylamino) propyl] phenothiazine monohydrochloride‬‬

‫ﺧﺼﺎﺋﺼﻪ ‪Properties‬‬
‫‪Chlorpromazine hydrochloride is an odorless, white crystalline powder. It is‬‬
‫‪freely soluble in water, alcohol, chloroform and insoluble in ether and benzene.‬‬
‫)ﻛﻠﻮﺭﺑﺮﻭﻣﺎﺯﻳﻦ ﻫﻮ ﻣﺴﺤﻮﻕ ﺃﺑﻴﺾ ﻣﺘﺒﻠﻮﺭ ﻋﺪﱘ ﺍﻟﺮﺍﺋﺤﺔ‪ ،‬ﻳﻨﺤﻞ ﺑﺴﻬﻮﻟﺔ ﰲ ﺍﳌﺎﺀ ﻭﺍﻟﻜﺤﻮﻝ ﻭﺍﻟﻜﻠﻮﺭﻭﻓﻮﺭﻡ ﻭﻋﺪﱘ ﺍﻻﳓﻼﻝ‬
‫ﰲ ﺍﻹﻳﺘﺮ ﻭﺍﻟﺒﱰﻥ(‪.‬‬

‫‪٢٧‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 :‫ ﺍﺻﻄﻨﺎﻋﻪ‬-
Chlorpromazine is synthesized by cyclization of 3-chlorodiphenylamine with
sulphur in presence of small amount of iodine as catalyst.
‫ﻛﻠﻮﺭﻭ ﺩﻱ ﻓﻴﻨﻴﻞ ﺃﻣﲔ ﻣﻊ ﺍﻟﻜﱪﻳﺖ ﺑﻮﺟﻮﺩ ﻛﻤﻴﺔ ﺻﻐﲑﺓ ﻣﻦ ﺍﻟﻴﻮﻡ‬-٣ ‫)ﻳﺘﻢ ﺍﺻﻨﻄﺎﻉ ﺍﻟﻜﻠﻮﺭﺑﺮﻭﻣﺎﺯﻳﻦ ﺑﻌﻤﻠﻴﺔ ﺣﻠﻘﻨﺔ ﺍﳌﺮﻛﺐ‬
.(‫ﻛﻤﺤﻔﺰ‬

Uses ‫ ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ‬-
1. Chlorpromazine is used in the management of psychotic conditions. It also
controls excitement, aggression and agitation.

.(‫ ﻛﻤﺎ ﺃﻧﻪ ﻳﺘﺤﻜﻢ ﺑﺎﻹﺛﺎﺭﺓ ﻭﺍﻟﻌﺪﻭﺍﻧﻴﺔ ﻭﺍﳍﻴﺠﺎﻥ‬،‫)ﻳﺴﺘﺨﺪﻡ ﺍﻟﻜﻠﻮﺭﺑﺮﻭﻣﺎﺯﻳﻦ ﰲ ﺍﻟﺘﻌﺎﻣﻞ ﻣﻊ )ﺇﺩﺍﺭﺓ( ﺍﳊﺎﻻﺕ ﺍﻟﻨﻔﺴﻴﺔ‬

2. It has antiemetic, antipruritic, anti-histaminic and sedative properties.

.(‫)ﻟﻪ ﺧﻮﺍﺹ ﻣﻀﺎﺩﺓ ﻟﻺﻗﻴﺎﺀ ﻭﻣﻀﺎﺩ ﻟﻠﺤﻜﺔ ﻭﻛﻤﻀﺎﺩ ﻫﻴﺴﺘﺎﻣﲔ ﻭﻟﻪ ﺗﺄﺛﲑ ﻣﻬﺪﺉ‬

٢٨ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
 Prochlorperazine ‫ﺑﺮوﻛﻠﻮرﺑﻴﺮازﻳﻦ‬

3-chloro-10-[3-(4-methyl-1-piperazinyl) phenothiazine
Properties ‫ ﺧﻮﺍﺻﻪ‬-
Prochlorperazine is a pale yellow colored, viscous liquid and is very slightly
soluble in water but freely soluble in alcohol.
.(‫ﺍ ﰲ ﺍﳌﺎﺀ ﻭﻟﻜﻦ ﻳﻨﺤﻞ ﺑﺴﻬﻮﻟﺔ ﰲ ﺍﻟﻜﺤﻮﻝ‬‫)ﺑﺮﻭﻛﻠﻮﺭﺑﲑﺍﺯﻳﻦ ﻫﻮ ﺳﺎﺋﻞ ﻟﺰﺝ ﺃﺻﻔﺮ ﺷﺎﺣﺐ ﺿﻌﻴﻒ ﺍﻻﳓﻼﻝ ﺟﺪ‬
‫ ﺍﺻﻄﻨﺎﻋﻪ‬-
Prochlorperazine is prepared by refluxing 1-(3-chloro propyl)-4 methylpiperazine
with 2-chlorophenothiazine in presence of sodamide in toluene.
‫ﻛﻠﻮﺭﻭﻓﻴﻨﻮﺛﻴﺎﺯﻳﻦ ﺑﻮﺟﻮﺩ‬-٢ ‫ ﻣﻴﺘﻞ ﺑﻴﺒﲑﺍﺯﻳﻦ ﻣﻊ‬٤-(‫ﻛﻠﻮﺭﻭ ﺑﺮﻭﺑﻴﻞ‬-٣)-١ ‫)ﻳﺘﻢ ﲢﻀﲑ ﺍﻟﱪﻭﻛﻠﻮﺭﺑﲑﺍﺯﻳﻦ ﺑﺈﺫﺍﺑﺔ‬
.(‫ ﰲ ﺍﻟﺘﻮﻟﻮﻳﻦ‬NaNH2 ‫ﺍﻟﺼﻮﺩﺍﻣﻴﺪ‬

Uses ‫ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ‬
1. Prochlorperazine is an antipsychotic and tranquilizing agent. It is used to
treat various psychiatric disorders such as schizophrenia, mania, involution
psychoses, senile and tonic psychoses.
،"‫ ﻳﺴﺘﺨﺪﻡ ﻟﻌﻼﺝ ﺍﻟﻌﺪﻳﺪ ﻣﻦ ﺍﻷﻣﺮﺍﺽ ﺍﻟﻨﻔﺴﻴﺔ ﻛﺎﻟﻔﺼﺎﻡ "ﺍﻟﺸﻴﺰﻭﻓﺮﻳﻨﻴﺎ‬.‫)ﺍﻟﱪﻭﻛﻠﻮﺭﺑﲑﺍﺯﻳﻦ ﻫﻮ ﻋﺎﻣﻞ ﻫﺪﺉ ﻭﻣﻀﺎﺩ ﻟﻠﺬﻫﺎﻥ‬
.(‫ ﺍﻟﺬﻫﺎﻥ ﺍﻟﺸﻴﺨﻮﺧﻲ ﻭﺍﻟﺬﻫﺎﻥ ﺍﻟﺘﻮﺗﺮﻱ‬،‫ ﺍﻟﺬﻫﺎﻥ ﺍﻻﻧﻄﻮﺍﺋﻲ‬،‫ﺍﳍﻮﺱ‬

2.It also has antiemetic properties.

.(‫)ﻛﻤﺎ ﺃﻥ ﺍﻟﻜﻠﻮﺭﺑﲑﺍﺯﻳﻦ ﻳﺘﻤﺘﻊ ﲞﻮﺍﺹ ﻣﻀﺎﺩﺓ ﻟﻺﻗﻴﺎﺀ‬

٢٩ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
 Trifluoperazine ‫ﺗﺮي ﻓﻠﻮ ﺑﻴﺮازﻳﻦ‬
10-[3-(4-methylpiperazin-1-yl)propyl]-2-trifluoromethyl methylphenothiazine

Properties ‫ﺧﺼﺎﺋﺼﻪ‬
Trifluoperazine occurs as hydrochloride salt. Trifluoperazine HCl is white to pale
yellow, crystalline powder. It is freely soluble in water.
‫ ﺳﻬﻞ ﺍﻻﳓﻼﻝ‬.‫ ﻭﺗﺘﻮﺍﺟﺪ ﻛﻤﺴﺤﻮﻕ ﺑﻠﻮﺭﻱ ﺃﺑﻴﺾ ﺇﱃ ﺃﺻﻔﺮ ﺷﺎﺣﺐ‬،‫)ﺗﺮﻱ ﻓﻠﻮ ﺑﲑﺍﺯﻳﻦ ﻳﺘﻮﺍﺟﺪ ﻛﺄﻣﻼﺡ ﲪﺾ ﻛﻠﻮﺭ ﺍﳌﺎﺀ‬
.(‫ﰲ ﺍﳌﺎﺀ‬

‫ ﺍﺻﻄﻨﺎﻋﻪ‬-
It is prepared by refluxing 2-trifluoromethyl phenothiazine and 3-(4-
methylpiperazinyl) propyl chloride in presence of sodamide as a base.
‫ﻣﻴﺘﻴﻞ ﺑﻴﺒﲑﺍﺯﻳﻨﻴﻞ( ﺍﻟﱪﻭﺑﻴﻞ ﺑﻮﺟﻮﺩ ﺍﻷﻣﻴﺪ‬-٤) -٣- ‫ ﻛﻠﻮﺭﻳﺪ‬‫ﺗﺮﻱ ﻓﻠﻮﺭﻭ ﻣﻴﺘﻴﻞ ﻓﻴﻨﻮ ﺛﻴﺎﺯﻳﻦ ﻭ‬-٢ ‫)ﻳﺘﻢ ﲢﻀﲑﻩ ﻋﱪ ﺇﺫﺍﺑﺔ‬
.(‫ ﻳﻠﻌﺐ ﺩﻭﺭ ﺃﺳﺎﺱ ﻗﻮﻱ‬:NaNH2 ‫ﺍﻟﺼﻮﺩﻱ )ﺍﻟﺼﻮﺩﺍﻣﻴﺪ‬

Uses ‫ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ‬
1. Triflupromazine is used to treat psychotic disorders.
.(‫)ﺗﺮﻱ ﻓﻠﻮ ﺑﺮﻭﻣﺎﺯﻳﻦ ﻳﺴﺘﺨﺪﻡ ﻟﻌﻼﺝ ﺍﻷﻣﺮﺍﺽ ﺍﻟﻨﻔﺴﻴﺔ‬
2. It also has antiemetic properties.
.(‫)ﻛﻤﺎ ﺃﻧﻪ ﻳﺘﻤﺘﻊ ﲞﻮﺍﺹ ﻣﻀﺎﺩﺓ ﻟﻺﻗﻴﺎﺀ‬

٣٠ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
 Promazine ‫ﺑﺮوﻣﺎزﻳﻦ‬
10-[3-(dimethylamino)-propyl] phenothiazine

Properties ‫ﺧﺼﺎﺋﺼﻪ‬
Promazine is available as hydrochloride salt. Promazine HCl is white or slightly
yellow crystalline powder, and is freely soluble in water and chloroform.
‫ ﻭﻫﻮ ﻣﺴﺤﻮﻕ ﺑﻠﻮﺭﻱ ﺃﺑﻴﺾ ﺃﻭ ﺃﺻﻔﺮ ﺧﻔﻴﻒ‬،(HCl ‫ ﳊﻤﺾ ﻛﻠﻮﺭ ﺍﳌﺎﺀ‬:‫)ﺍﻟﱪﻭﻣﺎﺯﻳﻦ ﻳﺘﻮﻓﺮ ﻛﺄﻣﻼﺡ ﻫﻴﺪﺭﻭﻛﻠﻮﺭﻳﺔ )ﻳﻌﲏ‬
.(‫ﻭﻳﻨﺤﻞ ﺑﺴﻬﻮﻟﺔ ﰲ ﺍﳌﺎﺀ ﻭﺍﻟﻜﻠﻮﺭﻭﻓﻮﺭﻡ‬

‫ ﺍﺻﻄﻨﺎﻋﻪ‬-
Promazine is prepared by condensing 3-chloro-N, N-di methyl propyl amine
with phenothiazine in presence of sodium hydride.
.(‫ ﺛﻨﺎﺋﻲ ﻣﻴﺘﻴﻞ ﺑﺮﻭﺑﻴﻞ ﺃﻣﲔ ﻣﻊ ﺍﻟﻔﻴﻨﻮﺛﻴﺎﺯﻳﻦ ﺑﻮﺟﻮﺩ ﻫﻴﺪﺭﻳﺪ ﺍﻟﺼﻮﺩﻳﻮﻡ‬-N,N-‫ﻛﻠﻮﺭﻭ‬-٣ ‫)ﺍﻟﱪﻭﻣﺎﺯﻳﻦ ﻳﺘﻢ ﲢﻀﲑﻩ ﺑﺘﻜﺜﻴﻒ‬

Uses ‫ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ‬
1. Promazine has antipsychotic properties.
.(‫)ﺍﻟﱪﻭﻣﺎﺯﻳﻦ ﻟﻪ ﺧﻮﺍﺹ ﻣﻀﺎﺩﺓ ﻟﻠﺬﻫﺎﻥ ﻭﺍﻷﻣﺮﺍﺽ ﺍﻟﻨﻔﺴﻴﺔ‬
2. It is also used to control nausea and vomiting.
.(‫)ﻛﻤﺎ ﺃﻧﻪ ﻳﺴﺘﺨﺪﻡ ﻟﻀﺒﻂ "ﻋﻼﺝ" ﺍﻟﻐﺜﻴﺎﻥ ﻭﺍﻹﻗﻴﺎﺀ‬

٣١ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
 ‫اﻟﺒﻮﺗﻴﺮوﻓﻴﻨﻮﻧﺎت‬
‫‪BUTYROPHENONES‬‬

‫اﻟﺒﻮﺗﻴﺮوﻓﻴﻨﻮﻧﺎت‪ :‬ﻋﻼﻗﺔ اﻟﺒﻨﻴﺔ ﺑﺎﻟﺘﺄﺛﻴﺮ‬

‫‪Structure-Activity Relationships of BUTYROPHENONES‬‬

‫‪ -‬ﻭﺟﻮﺩ ﳎﻤﻮﻋﺔ ﺍﻟﻜﺮﺑﻮﻧﻴﻞ ﺿﺮﻭﺭﻱ ﻟﻠﻔﻌﺎﻟﻴﺔ ﺍﳌﻀﺎﺩﺓ ﻟﻠﺬﻫﺎﻥ‪ ،‬ﻭﺇﻥ ﺍﺳﺘﺒﺪﺍﻝ ﻫﺬﻩ ﺍ‪‬ﻤﻮﻋﺔ ﲟﺠﻤﻮﻋﺎﺕ ﺍﺧﺮﻯ ﻳﻨﻘﺺ ﻣﻦ‬
‫ﺍﻟﻔﻌﺎﻟﻴﺔ ﻣﺜﻞ ‪ .... CH(OH), -CH(X), -O-, -S, -SO2‬ﺇﱁ‪.‬‬

‫‪ -‬ﻛﻞ ﺍﳌﺸﺘﻘﺎﺕ ﳚﺐ ﺍﻥ ﲢﺘﻮﻱ ﰲ ﺍﳌﻮﻗﻊ ﺑﺎﺭﺍ ﻣﻦ ﺣﻠﻘﺔ ﺍﻟﺒﱰﻥ ﻋﻠﻰ ﳎﻤﻮﻋﺔ ﻓﻠﻮﺭ‪ ،‬ﻭﺇﻥ ﺍﻟﻔﻌﺎﻟﻴﺔ ﺗﻨﻘﺺ ﻋﻨﺪ ﺍﺳﺘﺒﺪﺍﻝ ﺍﻟﻔﻠﻮﺭ‬
‫ﲟﺠﻤﻮﻋﺔ ﺃﺧﺮﻯ ﻣﺜﻞ ‪.H, Cl, CH3, OCH3 or Ar‬‬

‫‪ -‬ﺟﺴﺮ ﺍﻟﱪﻭﺑﻴﻠﲔ ﺿﺮﻭﺭﻱ ﻻﻋﻄﺎﺀ ﺍﳌﻮﺍﺻﻔﺎﺕ ﺍﳌﻀﺎﺩﺓ ﻟﻠﺬﻫﺎﻥ‪ ,‬ﻭﺇﻥ ﺗﻘﺼﲑ ﺃﻭ ﺗﻄﻮﻳﻞ ﻫﺬﺍ ﺍﳉﺴﺮ ﻳﻨﻘﺺ ﻣﻦ ﺍﻟﻔﻌﺎﻟﻴﺔ‪.‬‬
‫‪ -‬ﺇﻥ ﺩﻣﺞ ﺫﺭﺓ ﺍﻻﺯﻭﺕ ﰲ ﺣﻠﻘﺔ ﺳﺪﺍﺳﻴﺔ ﺿﺮﻭﺭﻱ ﻻﻋﻄﺎﺀ ﺍﻟﻔﻌﺎﻟﻴﺔ ﺍﳌﺜﺒﻄﺔ ﻟﻠـ ‪.CNS‬‬

‫‪ -‬أﻣﺜﻠﺔ‪:‬‬
‫‪Haloperidol‬‬

‫‪٣٢‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 ‫‪Pethidine‬‬ ‫‪Droperidol‬‬

‫ﻫﺎﻟﻮﺑﻴﺮﻳﺪول ‪Haloperidol‬‬
‫‪4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4′-fluorobutyrophenone.‬‬
‫ﺧﺼﺎﺋﺼﻪ ‪Properties‬‬
‫ﻣﺴﺤﻮﻕ ﺃﺑﻴﺾ ﻣﺼﻔﺮ ﻻ ﻳﻨﺤﻞ ﰲ ﺍﳌﺎﺀ ﻭﻗﻠﻴﻞ ﺍﻻﳓﻼﻝ ﰲ ﺍﻟﻐﻮﻝ ﻭﻳﻨﺤﻞ ﰲ ﺍﶈﻼﺕ ﺍﻟﻌﻀﻮﻳﺔ‪.‬‬
‫‪ -‬ﺍﺻﻄﻨﺎﻋﻪ‬
‫‪Haloperidol is synthesized by condensing 4-(4-chlorophenyl-4-piperidinol with‬‬
‫‪4- chloro-4′-fluorobutyrophenone:‬‬
‫)ﻳﺘﻢ ﺍﺻﻄﻨﺎﻉ ﺍﳍﺎﻟﻮﺑﲑﻳﺪﻭﻝ ﺑﺘﻜﺜﻴﻒ ‪-٤)-٤‬ﻛﻠﻮﺭﻭﻓﻴﻨﻴﻞ‪-٤-‬ﺑﻴﺒﲑﻳﺪﻳﻨﻮﻝ ﻣﻊ ‪-٤‬ﻛﻠﻮﺭﻭ‪-'٤-‬ﻓﻠﻮﺭﻭ ﺑﻮﺗﲑﻭ ﻓﻴﻨﻮﻥ(‪.‬‬

‫ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ ‪Uses‬‬
‫‪ .١‬ﻣﻀﺎﺩ ﻟﻠﺬﻫﺎﻥ ﻗﻮﻱ ﺟﺪ‪‬ﺍ )ﺃﻗﻮﻯ ﻣﻦ ﺍﻟﻜﻠﻮﺭﺑﺮﻭﻣﺎﺯﻳﻦ(‪.‬‬
‫‪ .٢‬ﻳﺴﺘﻌﻤﻞ ﰲ ﺍﻻﺿﻄﺮﺍﺑﺎﺕ ﺍﻟﻨﻔﺴﻴﺔ ﺍﳊﺎﺩﺓ ﻭﺍﻟﺬﻫﺎﻥ ﺍﻟﻌﺼﱯ ﺍﻟﻌﺎﻃﻔﻲ ﻭﺍﻧﻔﺼﺎﻡ ﺍﻟﺸﺨﺼﻴﺔ‪.‬‬

‫‪٣٣‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 ‫ﻣﺸﺘﻘﺎت ﺛﻴﻮﻛﺰاﻧﺘﻴﻦ‬
‫‪Thioxanthenes‬‬

‫‪Chlorprothixene‬‬ ‫‪Flupenthixol‬‬ ‫‪Zuclopenthixol‬‬

‫ﻣﻀﺎدات اﻟﺼﺮع‬
‫‪Anti-Epileptic Drugs‬‬

‫‪ -‬اﻟﺼﺮع أو داء اﻟﺴﻘﻮط ‪ Falling Disease‬ﺃﻭ ﻣﺎ ﻳﺪﻋﻰ ﻋﻨﺪ ﺍﻟﻌﺎﻣﺔ ﺑﺎﻟﺴﺎﻋﺔ‪:‬‬

‫ﻣﺮﺽ ﻳﺘﺼﻒ ﺑﺎﻧﻔﺮﺍﻍ ﺷﺤﻨﺎﺕ ﻛﻬﺮﺑﺎﺋﻴﺔ ﺩﻣﺎﻏﻴﺔ ﻏﲑ ﻃﺒﻴﻌﻴﺔ‪ ،‬ﻭﻳﺄﰐ ﺑﺸﻜﻞ ﻧﻮﺏ ﻣﻔﺎﺟﺌﺔ ﻭﻣﻌﺎﻭﺩﺓ )ﻣﺘﻜﺮﺭﺓ( ﻣﻦ ﺇﺣﺪﻯ ﺍﻟﺒﺆﺭ‬
‫ﺍﻟﺪﻣﺎﻏﻴﺔ‪.‬‬

‫‪ -‬ﺍﻟﺼﻔﺔ ﺍﻷﺳﺎﺳﻴﺔ ﻟﻠﺼﺮﻉ ﻫﻲ ﻓﻘﺪﺍﻥ ﺍﻟﻮﻋﻲ ﺍﻟﺬﻱ ﺗﻠﻴﻪ ﻣﺮﺣﻠﺔ ﺍﻟﺘﺸﻨﺠﺎﺕ ﺍﻟﺘﻮﺗﺮﻳﺔ ﻭﺍﻻﺧﺘﻼﺟﺎﺕ ﺍﻟﻌﻀﻠﻴﺔ ﻭﻳﺘﺮﺍﻓﻖ‬
‫ﺑﺎﺿﻄﺮﺍﺏ ﺍﳊﺲ ﻭﺍﻟﺸﻌﻮﺭ ﻭﺍﺿﻄﺮﺍﺏ ﰲ ﺍﳉﻬﺎﺯ ﺍﻟﻌﺼﱯ ﺍﻟﺬﺍﰐ‪ ،‬ﻳﺼﻴﺐ ﺍﻟﻜﺒﺎﺭ ﻭﺍﻟﺼﻐﺎﺭ ﰲ ﲨﻴﻊ ﺍﻷﻋﻤﺎﺭ ﻭﻻ ﻳﻔﺮﻕ ﺑﲔ‬
‫ﺍﳉﻨﺲ )ﻳﺼﻴﺐ ﺍﻟﺬﻛﻮﺭ ﻭﺍﻹﻧﺎﺙ(‪.‬‬

‫‪٣٤‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 :‫ أﻣﻜﻦ ﺗﻤﻴﻴﺰ أﺷﻜﺎل ﻋﺪﻳﺪة ﻟﻠﺼﺮع ﻫﻲ‬:‫ اﻷﺷﻜﺎل اﻟﺴﺮﻳﺮﻳﺔ ﻟﻠﺼﺮع‬-
Minor Epilepsy . ‫ ﺍﻟﺼﺮﻉ ﺍﻟﺼﻐﲑ‬.٢ Major Epilepsy . ‫ ﺍﻟﺼﺮﻉ ﺍﻟﻜﺒﲑ‬.١
Myoclonic Epilepsy . ‫ ﺍﻟﺼﺮﻉ ﺍﻟﺮﻣﻌﻲ ﺍﳊﺮﻛﻲ‬.٣
Infanitile Epilepsy. ‫ ﻭﻳﺴﻤﻰ ﺑﺼﺮﻉ ﺍﻟﺴﻼﻡ‬،‫ ﺍﻟﺼﺮﻉ ﺍﻟﻄﻔﻠﻲ ﺍﻟﺘﺸﻨﺠﻲ‬.٤
Psychomotor Epilepsy . ‫ ﺍﻟﺼﺮﻉ ﺍﻟﻨﻔﺴﻲ ﺍﳊﺮﻛﻲ‬.٥
.‫ ﺍﻟﺼﺮﻉ ﺍﳉﺎﻛﺴﻮﱐ )ﺍﻟﺼﺮﻉ ﺍﳊﺮﻛﻲ( ﻷﻥ ﺃﻭﻝ ﻣﻦ ﺍﻛﺘﺸﻔﻪ ﺍﻟﻄﺒﻴﺐ ﺍﻹﻧﻜﻠﻴﺰﻱ ﺟﺎﻛﺴﻮﻥ‬.٦
Status Epilepticus ‫ ﺍﳊﺎﻟﺔ ﺍﻟﺼﺮﻋﻴﺔ ﺍﳌﺘﺪﺍﺧﻠﺔ‬.٨ Sensory Epilepsy . ‫ ﺍﻟﺼﺮﻉ ﺍﳊﺴﻲ‬.٧

‫ﻣﻀﺎدات اﻟﺼﺮع‬
Anti Epileptic Drugs

1. Aldehydes 2. Aromatic allylic alcohols 3. Barbiturates

4. Benzodiazepines 5. Bromides 6. Carbamates
7. Carboxamides 8. Fatty acids 9. Fructose derivatives
10. Gaba analogs 11. Hydantoins 12. Oxazolidinediones
13. Propionates 14. Pyrimidinediones 15. Pyrrolidines
16. Succinimides 17. Sulfonamides 18. Triazines
19. Ureas 20. Valproylamides (amide derivatives of valproate)

‫ﻣﺸﺘﻘﺎت اﻟﺒﻮﻟﺔ‬
UREAS
:‫ﻫﻲ ﻋﺒﺎﺭﺓ ﻋﻦ ﻣﺮﻛﺒﺎﺕ ﺃﻣﻴﺪﻳﺔ ﻣﺸﺘﻘﺔ ﻣﻦ ﺍﻟﺒﻮﻟﺔ ﻭﺗﻘﺴﻢ ﺍﱃ ﻗﺴﻤﲔ‬
.(‫ ﺫﺍﺕ ﺳﻠﺴﻠﺔ ﻣﻔﺘﻮﺣﺔ ﻣﺜﻞ ﺍﻟﻔﻴﻨﺎﺳﻴﻤﻴﺪ ﻭﺍﻻﻳﺘﻴﻞ ﻓﻴﻨﺎﺳﻴﻤﻴﺪ )ﻓﻴﻨﺎﺗﻮﺭﻳﺪ‬-
‫ ﺫﺍﺕ ﺳﻠﺴﺔ ﻣﻐﻠﻘﺔ‬-

Pheneturide Phenacemide
‫ﻓﻴﻨﻴﻞ ﺑﻮﺗﲑﻳﻞ ﺍﻟﺒﻮﻟﺔ‬ ‫ﻓﻴﻨﻴﻞ ﺍﺳﻴﺘﻴﻞ ﺍﻟﺒﻮﻟﺔ‬

٣٥ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
 ‫ﻣﺸﺘﻘﺎت اﻟﻬﻴﺪاﻧﺘﻮﺋﻴﻦ‬
‫‪Hydantoins‬‬

‫ﻭﻫﻮ ﻳﻌﺘﱪ ﻣﻦ ﻣﺸﺘﻘﺎﺕ ﺍﻟﺒﻮﻟﺔ ﺫﺍﺕ ﺍﻟﺴﻠﺴﻠﺔ ﺍﳌﻐﻠﻘﺔ‪.‬‬

‫‪ -‬ﺗﺘﻤﻴﺰ ﺍﳍﻴﺪﺍﻧﺘﻮﺋﻴﻨﺎﺕ ﺑﺄ‪‬ﺎ ﲤﻠﻚ ﻣﻮﺍﺻﻔﺎﺕ ﲪﻀﻴﺔ ﺃﺿﻌﻒ ﻣﻦ ﺍﻟﺒﺎﺭﺑﻴﺘﻮﺭﺍﺕ ﻭﺑﺎﻟﺘﺎﱄ ﻓﺈﻥ ﳏﺎﻟﻴﻞ ﺃﻣﻼﺣﻬﺎ ﺍﻟﺼﻮﺩﻳﺔ ﺗﻜﻮﻥ‬
‫ﺃﻛﺜﺮ ﻗﻠﻮﻳﺔ ﻣﻦ ﺍﶈﺎﻟﻴﻞ ﺍﻟﺼﻮﺩﻳﺔ ﻟﻠﺒﺎﺭﺑﻴﺘﻮﺭﺍﺕ‪.‬‬
‫‪ -‬ﺇﻥ ﺍﻟﻔﻌﺎﻟﻴﺔ ﺍﻟﺴﺮﻳﺮﻳﺔ ﻟﻠﻬﻴﺪﺍﻧﺘﻮﺋﻴﻨﺎﺕ ﺗﺮﺗﺒﻂ ﺑﺸﻜﻞ ﺭﺋﻴﺴﻲ ﺑﻮﺟﻮﺩ ﳎﻤﻮﻋﺔ ﺃﺭﻳﻠﻴﺔ ﰲ ﺍﳌﻮﻗﻊ ﺭﻗﻢ ‪.٥‬‬
‫‪ -‬ﲤﻠﻚ ﺗﺄﺛﲑ ﻣﺰﺩﻭﺝ ﻓﻬﻲ ﻣﻬﺪﺋﺔ ﻭﻣﻨﻮﻣﺔ ﻣﻦ ﺟﻬﺔ ﻭﻣﻀﺎﺩﺓ ﻟﻠﺼﺮﻉ ﻣﻦ ﺟﻬﺔ ﺍﺧﺮﻯ‪.‬‬

‫ﻓﻴﻨﻴﺘﻮﻳﻦ ‪Phenytoin‬‬
‫‪5, 5′-diphenylhydantoin‬‬

‫ﺧﺼﺎﺋﺼﻪ ‪Properties‬‬
‫‪Phenytoin occurs as white, crystalline powder, slightly hygroscopic, soluble in‬‬
‫‪water and in alcohol, practically insoluble in ether and in methylene chloride.‬‬
‫)ﺍﻟﻔﻴﻨﻴﺘﻮﻳﻦ ﻳﺘﻮﺍﺟﺪ ﻛﻤﺴﺤﻮﻕ ﺃﺑﻴﺾ ﺑﻠﻮﺭﻱ ﻣﺴﺘﺮﻃﺐ ﺑﺸﻜﻞ ﺿﻌﻴﻒ‪ ،‬ﻭﻫﻮ ﻳﻨﺤﻞ ﰲ ﺍﳌﺎﺀ ﻭﺍﻟﻜﺤﻮﻝ‪ ،‬ﻭﻋﻤﻠﻴ‪‬ﺎ ﻻ ﻳﻨﺤﻞ ﰲ‬
‫ﺍﻹﻳﺘﺮ ﻭﻛﻠﻮﺭﻳﺪ ﺍﳌﻴﺘﻠﲔ(‪.‬‬
‫‪ -‬ﺍﺻﻄﻨﺎﻋﻪ‬
‫‪Phenytoin may be synthesized by heating α-bromodiphenylacetylurea with‬‬
‫‪alcoholic ammonia.‬‬
‫)ﻳﺘﻢ ﺍﺻﻄﻨﺎﻉ ﺍﻟﻔﻴﻨﻴﺘﻮﻳﻦ ﺑﺘﺴﺨﲔ ‪-α‬ﺑﺮﻭﻣﻮ ﺛﻨﺎﺋﻲ ﻓﻴﻨﻴﻞ ﺃﺳﺘﻴﻞ ﻳﻮﺭﻳﺎ ﻣﻊ ﺍﻷﻣﻮﻧﻴﺎ ﺍﻟﻜﺤﻮﻟﻴﺔ(‪.‬‬

‫‪٣٦‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬

 Uses ‫ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ‬
1. Phenytoin is used alone or in combination with phenobarbital in the
treatment of grand mal and psychomotor epilepsy.
.(‫)ﻳﺴﺘﺨﺪﻡ ﺍﻟﻔﻴﻨﻴﺘﻮﻳﻦ ﻟﻮﺣﺪﻩ ﺃﻭ ﺑﺎﳌﺸﺎﺭﻛﺔ ﻣﻊ ﺍﻟﻔﻴﻨﻮﺑﺎﺭﺑﻴﺘﺎﻝ ﳌﻌﺎﳉﺔ ﺍﻟﺼﺮﻉ ﺍﻟﺘﺸﻨﺠﻲ ﺍﻟﻼﻭﺍﻋﻲ ﻭﺍﻟﺼﺮﻉ ﺍﳊﺮﻛﻲ ﺍﻟﻨﻔﺴﻲ‬
2. It is also used in the treatment of other types of convulsions.
.(‫)ﻛﻤﺎ ﺃﻧﻪ ﻳﺴﺘﺨﺪﻡ ﳌﻌﺎﳉﺔ ﺃﻧﻮﺍﻉ ﺃﺧﺮﻯ ﻣﻦ ﺍﻻﺧﺘﻼﺟﺎﺕ‬

MEPHENYTOIN ‫ﻣﻴﻔﻴﻨﺘﻮﻳﻦ‬
5-ethyl-3-methyl-5-phenylhdantoin.

Properties ‫ﺧﺼﺎﺋﺼﻪ‬
Mephenytoin is water insoluble, colorless crystalline solid. It forms a water
soluble sodium salt which has an alkaline reaction.
‫ ﻛﻤﺎ ﺃﻥ ﻣﻠﺤﻪ ﺍﻟﺼﻮﺩﻱ ﻣﻨﺤﻞ ﰲ ﺍﳌﺎﺀ‬.‫ ﻭﻫﻮ ﻋﺒﺎﺭﺓ ﻋﻦ ﺑﻠﻮﺭﺍﺕ ﺻﻠﺒﺔ ﻋﺪﳝﺔ ﺍﻟﻠﻮﻥ‬،‫)ﺍﳌﻴﻔﻴﻨﺘﻮﻳﻦ ﻋﺪﱘ ﺍﻻﳓﻼﻝ ﰲ ﺍﳌﺎﺀ‬
(‫ﻭﻳﻌﻄﻲ ﺗﻔﺎﻋﻞ ﻗﻠﻮﻱ‬
‫ ﺍﺻﻄﻨﺎﻋﻪ‬-
Mephenytoin is prepared by the following steps:
:(‫)ﻳﺘﻢ ﲢﻀﲑ ﺍﳌﻴﻔﻴﻨﺘﻮﻳﻦ ﻋﱪ ﺍﳋﻄﻮﺍﺕ ﺍﻟﺘﺎﻟﻴﺔ‬
1. In the first step cyano ethyl phenyl acet amide is prepared from cyano phenyl
acet amide by treatment with sodium ethoxide and ethyl iodide.
‫ ﺇﻳﺘﻮﻛﺴﻴﺪ ﺍﻟﺼﻮﺩﻳﻮﻡ‬:‫ ﻳﺘﻢ ﲢﻀﲑ ﺳﻴﺎﻧﻮ ﺇﻳﺘﻴﻞ ﻓﻴﻨﻴﻞ ﺃﺳﻴﺖ ﺃﻣﻴﺪ ﻣﻦ ﺳﻴﺎﻧﻮ ﻓﻴﻨﻴﻞ ﺃﺳﻴﺖ ﺃﻣﻴﺪ ﲟﻌﺎﳉﺘﻪ ﺑـ‬:‫)ﺍﳋﻄﻮﺓ ﺍﻷﻭﱃ‬
.(‫ﻭﻳﻮﺩﻳﺪ ﺍﻹﻳﺘﻴﻞ‬

٣٧ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
2. The product obtained by oxidation with alkaline hypobromite solution
converts cyano group of cyano ethyl phenyl acet amide to amide group, which
isomerizes and cyclized Spontaneously.
‫)ﻋﻨﺪ ﺗﻌﺮﻳﺾ ﻧﺎﺗﺞ ﺍﻟﺘﻔﺎﻋﻞ ﺍﻟﺴﺎﺑﻖ ﺇﱃ ﺍﻷﻛﺴﺪﺓ ﺑﻮﺍﺳﻄﺔ ﳏﻠﻮﻝ ﺍﳍﻴﺒﻮﺑﺮﻭﻣﻴﺖ ﺗﺘﺄﺛﺮ ﳎﻤﻮﻋﺔ ﺍﻟﺴﻴﺎﻧﻮ ﰲ ﺍﻟﺴﻴﺎﻧﻮ ﺇﻳﺘﻴﻞ ﻓﻴﻨﻴﻞ‬
.(‫ﺎ‬‫ ﺗﻠﻘﺎﺋﻴ‬-‫ﺗﺸﻜﻞ ﺣﻠﻘﺔ‬- ‫ ﻭﺍﻟﱵ ﺗﺘﺤﻮﻝ ﺇﱃ ﺍﻹﻳﺰﻭﻣﲑ ﺍﻵﺧﺮ ﻭﺗﺘﺤﻠﻖ‬،‫ﺃﺳﻴﺖ ﺃﻣﻴﺪ ﻓﺘﺘﺤﻮﻝ ﺇﱃ ﳎﻤﻮﻋﺔ ﺃﻣﻴﺪ‬

3. The above cyclized product (5-ethyl 5-phenyl hydantoin) yield mephenytoin

by methylation of the nitrogen atom (which is present between two carbonyl
group) with methyl sulfate or methyliodide.
،"‫ﻓﻴﻨﻴﻞ ﻫﻴﺪﺍﻧﺘﻮﻳﻦ" ﺗﻨﺘﺞ ﺍﳌﻴﻔﻴﻨﻴﺘﻮﻳﻦ ﻋﱪ ﻣﺘﻴﻠﺔ ﺫﺭﺓ ﺍﻷﺯﻭﺕ "ﺍﳌﻮﺟﻮﺩﺓ ﺑﲔ ﳎﻤﻮﻋﱵ ﻛﺮﺑﻮﻧﻴﻞ‬-٥ ‫ﺇﻳﺘﻴﻞ‬-٥" ‫)ﺍﳊﻠﻘﺔ ﺍﻟﻨﺎﲡﺔ‬
.(‫ﻭﺗﺘﻢ ﻋﻤﻠﻴﺔ ﺍﳌﺘﻴﻠﺔ ﺑﻮﺍﺳﻄﺔ ﻛﱪﻳﺘﺎﺕ ﺍﳌﻴﺘﻴﻞ ﺃﻭ ﻳﻮﺩﻳﺪ ﺍﳌﻴﺘﻴﻞ‬

Clinical uses ‫ﺍﻻﺳﺘﺨﺪﺍﻣﺎﺕ ﺍﻟﺴﺮﻳﺮﻳﺔ‬

1. Mephenytoin is used to control seizures in combination with phenytoin
.(‫)ﺍﳌﻴﻔﻴﻨﻴﺘﻮﻳﻦ ﻳﺴﺘﺨﺪﻡ ﻟﻠﻀﺒﻂ ﺍﻟﻨﻮﺑﺎﺕ ﺑﺎﳌﺸﺎﺭﻛﺔ ﻣﻊ ﺍﻟﻔﻴﻨﻴﺘﻮﻳﻦ‬
2. It is used as a reserve drug (only when phenytoin has failed), because the
metabolic product (5-ethyl-5-phenylhydantoin) of mephenytoin is highly toxic.
-٥-‫ﺇﻳﺘﻴﻞ‬-٥" ‫ ﻷﻥ ﺃﺣﺪ ﻣﺴﺘﻘﻠﺒﺎﺕ ﺍﳌﻴﻔﻴﻨﻴﺘﻮﻳﻦ‬،‫)ﻳﺴﺘﺨﺪﻡ ﻛﺪﻭﺍﺀ ﺍﺣﺘﻴﺎﻃﻲ ﺭﺩﻳﻒ ﻻﻳﺴﺘﻌﻤﻞ ﺇﻻ ﻋﻨﺪﻣﺎ ﻳﻔﺸﻞ ﺍﻟﻔﻴﻨﻴﺘﻮﻳﻦ‬
.(‫ﻓﻴﻨﻴﻞ ﻫﻴﺪﺍﻧﺘﻮﻳﻦ" ﻟﻪ ﲰﻴﺔ ﻋﺎﻟﻴﺔ‬

٣٨ ‫ ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬.‫ﺩ‬
 ‫‪Urech Hydantoin Synthesis‬‬

‫_____________‬

‫ﯾﻤﻜﻨﻜﻢ اﻟﺤﺼﻮل ﻋﻠﻰ اﻟﻨﺴﺨﺔ اﻻﻟﻜﺘﺮوﻧﯿﺔ ﻋﻠﻰ اﻟﻤﻮﻗﻊ‪:‬‬

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‫‪٣٩‬‬ ‫ﺩ‪ .‬ﻧﺒﻴﻪ ﻟﻮﻟﻚ‬