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H
N
N
NH
Burimamide
CH 3
CH 3
HN
H
N
H
N
S
N
CH 3
S
Metiamide
cimetidine
* Administered
mg per day.
* disadvantages: ) not completely absorbed if administered with antacids
or sucralfate. ) inhibit the liver microsomal enzyme system CYP
,
what leads to decrease metabolism of phenytoin, theophylline, diazepins.
) affect potency in male.
ranitidine
N- -[ -(dimethylaminomethyl)furfurylthio]ethyl-N
- -nitro- , -ethendiamine.
- -methyl
* administered
mg per day
* weak inhibitor of liver microsomal enzyme system so it can be
administered with drugs comntraindicated in case of cimetidine.
famotidine
-[ -(diaminomethyleneamino)thiazol- -yl]methylthio
-N-sulfamoylproionamidine
* administered mg once or mg twice daily.
SAR of H2-antagonists.
1-immidazole ring is not required for competitive antagonism at the
H2-receptor, other heterocyclic rings can be used like furan and
thiazole.
2-Separation between the nitrogen atom and heterocyclic ring by 4
carbon atoms gives optimum activity
.
3-The terminal nitrogen atom should be polar and non basic for
maximal 4-antagonistic activity, while groups that are positively
charged at physiologic ph have agonistic activity.
4-Antagonistic activity is inversely proportional to hydrophilicity of
the nitrogen atom, but the hydrophilic nitrogen group in
ranitidine is an exception.
N
S CH2
N
Omeprazole
5-OCH3
Lansoprazole
Pantoprazole
b-OCHF2
3- OCH3 , 4-OCH3
Rabeprazole
omeprazole