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Gastro-Intestinal Tract Drugs

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Gastro-Intestinal Tract Drugs Faculty of Pharmacy Pharmaceutical Chemistry Department Gastro-Intestinal Tract Drugs Gastro-Intestinal Tract Drugs • Laxative 1-Bulk laxative (hydrophyllic agents) 2-Stimulant laxative (stimulate peristaltic movement and defecation) 3-Fecal softener (decrease surface tension of fecal matter and increase fluid penetration) • Anti-diarrheal 1-Opiod analogues 2-Enkaphalinase inhibitors • Prokinetic drugs • Emetics and antiemetics • Drugs used in peptic ulcer 1-H2 antagosnist 2-Proton pump inhibitor 3- treatment of helicobacter pylori Laxatives [i] Bulk Laxatives (Bulk forming laxatives or bulking agents) Cause retention of fluid fecal mass stimulate peristalsis 1- Hydrophillic agents Examples: [1] Methylcellulose: Partially methylated derivative of cellulose hydrophilic & non- absorbable. [2] Wheat Bran Fibrous outer layer of cereal grains, contain cellulose, polysaccharides, fats, proteins ii- Stimulant Laxatives (contact laxatives) [1] Synthetic diphenol laxatives Bisacodyl O CO CH3 N O CO CH3 M.O.A: • Direct contact of ACTIVE SUBSTANCE [BISPHENOL DEACETYL METABOLITE] formed by hydrolysis by bacterial enzymes in gut with sensory nerve endings in lower part of alimentary tract peristalsis of colon rapid onset if taken rectally. ii- Stimulant Laxatives (contact laxatives) (cont.) 2) Naturally occurring laxatives [Castor oil] Inactive triglycerides hydrolyzed by pancreatic lipase Glycerol + Ricinoleic acid. Ricinoleic acid re-absorption of fluid & electrolytes + peristalsis defection in short time. This effect may last several days Chronic use colics, dehydration, disturbance in electrolyte balance, malabsorption of vital substances, damage of intestinal mucosa. 3) Naturally ocuring Anthraquinone laxatives [Senna, Rhubarb, Aloes, Cascara, Frangula] Stimulate propulsive peristalsis of colon by local irritation alter absorption of electrolyte & water from colon, fluid accumulation & laxation. • [iii] Fecal softeners (Emollient laxatives) Surface tension of feces penetration of intestinal fluids 1) Paraffin oil: It's mineral oil if taken with food; it's absorbed causing FOREIGN BODY GRANULOMA avoid taking with food. Its use hypovitaminosis of fat soluble vitamins so, use ONLY in organic solvent poisoning. 2) Glycerol: Act by osmotic effect, lubricant, peristalsis. 3) Dioctyl sodium sulfosuccinate: Surface tension NOT used with paraffin [it absorption of paraffin by emulsification foreign body granuloma]. [iv] Osmotic laxatives 1) Sodium sulphate (Glauber’s salt) Poorly absorbed from GIT fluid accumulation by osmotic effect. NEVER used as hypertonic solution due to danger of dehydration &thrombosis 2) Magnesium sulphate (Epsom salts) The same as Glauber salt. 3) Sugar and sugar alcohols [Mannitol, sorbitol, Lactose & Lactulose] Lactulose [Duphalac®] Synthetic sugar used in treatment of constipation and encephalopathy. Disaccharide [Fructose, Galactose] pass stomach unaltered not hydrolyzed by enzymes of small intestine. In large intestine microflora cleaves it into short chained fatty acids [especially lactic & acetic acid] acidify intestinal content retain water in lumen & peristalsis. RETAIN NH3 IN COLON IN FORM OF NH4+ AMMONIA CONCENTRATION IN BRAIN & BLOOD WHICH IS INCREASED IN HEPATIC ENCEPHALOPATHY. Anti-Diarrheals 1) Opioid analogs: Diphenoxalate HCl (Lomotil®) Loperamide HCl (Imodium®) H O 4 N 2 N 3 2 H Cl 3 NC 1 N 1 Et O O OH metabolism MOA Act on & receptors inhibit peristalsis reflex Any -agonist cause constipation as a side effect. Side abuse Does not cause abuse due to its low effects bioavailability and works only in intestine Used in combination with atropine for symptomatic Used as anti-diarrheal in case treatment of diarrhea. This combination adverse of gastroenteritis or inflammatory effect of atropine limit abuse of opioid bowel disease sub-therapeutic dose of atropine causes tachycardia, if patient abuse drug will suffer from severe tachycardia Metabolism Into Difenoxin (free carboxylic acid derivative; 5 times more active and highly polar which reduce risk of CNS penetration and reduce abuse potential 2) Enkephalinase Inhibitors Enkephalinase inactivation of endogenous opiods by inhibition of this enzyme, endogenous opioids which inhibit peristalisis Racecadotril Prokinetic Drugs They stimulate motility of GIT causing stronger contraction without affecting their rhythm. Used in bloating and irritable bowel syndrome Prokinetic Drugs They stimulate motility of GIT causing stronger contraction without affecting their rhythm. Used in bloating and irritable bowel syndrome Domperidone (Motilium ®) Metocloperamide (Primperan®) Bulky gp antagonism M.O.A: Domperidone & Metoclopramide Peripheral dopamine (D2)-Antagonist Metoclopramide Peripheral 5-HT4 stimulant Ach release stimulate motor neurons [peristalisis] S.E: EPS [from dopamine blockage], Cramps & diarrhea [from Ach release] Domperidone with advantage over metoclopramide NO CNS side effects [NOT cross BBB]. Emetics and Anti-emetics 1- Emetics • Apomorphine HCl • Used for intoxication. • By Injection action within few minutes. N CH3 HO HO 2-Anti-emetics • General M.O.A: 1- Suppression of CTZ "Chemoreceptor Trigger Zone" 2- Action on vestibular apparatus [cause of motion sickness] 1- Tropane alkaloids Scopolamine, hyocyamine I.M. [in motion sickness]. 2- Phenothiazine derivatives Dopamine (D2) antagonist used as antiemetic S N X (CH ) 2 3 N N CH3 x=cl Prochlorperazine x=CF3 Trifluoperazine 3- Benzhydryl Derivatives [H1-antagonist Motion Sickness and antiemetic] Cyclizine (Emetrex) Meclizine(Ezadoxin) H H H2 N N CH3 Cl N N C CH3 Motion sickness Anti-emetic 4 - Metoclopramide • N.B Metoclopramide [central D2-antagonist & 5-HT3- antagonist] Anti-emetic. Metoclopramide [peripheral D2-antagonist & 5-HT4- agonist] Prokinetic. Drugs used in peptic ulcer 1- H2 antagonist 2- Proton pump inhibitors 3- Treatment of helicobacter pylorri H2 -Antagonists 1st generation H 2 antagonist Cimetidine [Tagamet®] N CN H3C CH2 S CH2 C H2 NH C NH CH3 Cynao guanidine HN N Effective gastric anti-secretory for duodenal ulcer but with high limitations So it was withdrawn from market. Side effects: Competetive inhibitor of dihydrotestesterone - gynecomastia in male -Sexual dysfunction in male -Galactorrhea in female - affect metabolism of other drugs by interfering with CYP450 nd 2 Generation H2-antagonists without imidazole [Other heterocylces may potency & selectivity for H2-receptors] Famotidine Nizatidine Guanidine CH2 S CH2 CH2 C NH2 NH2 N N SO NH C 2 2 H N 2 N S Thiazole ring Amino sulfonyl imidamine • Interference with CYP450 • No inhibitory action on Cytochrome enzymes. Ranitidine [Zantac®] CH3 N CH NO2 H3C O CH2 S CH2 CH 2 NH NH CH3 dimethyl amino methyl Furan ring N-methyl-2-n itro-1,1-ethene diamine [instead of cyanoguanidine] o Weak inhibitor of hepatic cytochrome enzymes. o Some antacids may its absorption. PROTON PUMP INHIBITORS [PPI] • They act on final step in acid secretion in parietal cell [Pumping of protons] • Membrane pump [H+/K+-ATPase] catalyze exchange of H+ for K+. • Benzimidazoles are NOT the active inhibitor of H+/K+-ATPase BUT transformed within acid compartment of parietal cells to an inhibitor molecule that react covalently with essential thiol [SH] function of the enzyme. OR OR OR X X O H + N N X H3O ATPase SH S N S S S ATPase N N NH Y N N N Y Y [Active form] Omeprazole Lansoprazole Benzoimidazole irreversible inhibitor Combination therapy in H.pylori infections: Majority of peptic ulcers related to H. pylori infections and NSAIDs therapy Several regimens of antibiotics, widely used with PPIs or less commonly with H2 receptor antagonists are effective. Double or triple drug combinations are used such as PPI + amoxicillin and clarithromycin or metronidazole. .
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