Omeprazole Basic information
Uses Mechanisms of Action Drug Interactions Adverse reactions Preparation
Product Name: Omeprazole
Synonyms: 1h-benzimidazole,5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulf;2-Chloromethyl-3,5-dinmethyl-4-methoxypyridine;5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl)benzimidazol;audazol;aulcer;belmazol;ceprandal;elgam
CAS: 73590-58-6
MF: C17H19N3O3S
MW: 345.42
EINECS: 201-212-8
Product Categories: Drug bulk;Active Pharmaceutical Ingredients;Omeprazole;Intermediates & Fine Chemicals;Pharmaceuticals;API's;ATPase;Metabolite Reference Standard;Isotopically Labeled Pharmaceutical Reference Standard;OSMITROL;Other APIs;Digestive System
Mol File: 73590-58-6.mol
Omeprazole Structure
Omeprazole Chemical Properties
Melting point 156°C
Fp 9℃
storage temp. 2-8°C
solubility H2O: 0.5 mg/mL
form solid
color white
Water Solubility Soluble in water (0.5 mg/ml), DMSO (25 mg/ml), and ethanol (4.5 mg/ml).
Merck 14,6845
Stability: Stable, but hygroscopic and photosensitive. Incompatible with strong oxidizing agents. Store in the dark.
CAS DataBase Reference 73590-58-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,T,F
Risk Statements 36/37/38-39/23/24/25-23/24/25-11
Safety Statements 26-36-37/39-45-36/37-16-7
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 2
RTECS DD9087000
Hazardous Substances Data 73590-58-6(Hazardous Substances Data)
MSDS Information
Provider Language
5-Methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-3H-benzoimidazole English
SigmaAldrich English
Omeprazole Usage And Synthesis
Uses Omeprazole is a proton pump inhibitor used to treat diseases like gastroesophageal reflux disease (GERD), used for gastric and duodenal ulcers, reflux or erosive esophagitis, and Zollinger-Ellison syndrome. It is also effective for gastric and duodenal ulcers that are ineffective with H2 receptor antagonists. Injections of Omeprazole can also be used for: 1 gastrointestinal bleeding, such as peptic and anastomic ulcer bleeding, and the prevention of severe diseases (such as cerebral hemorrhage, severe trauma, etc.) and gastric surgery caused by upper intestinal bleeding; 2 acute gastric mucosal damage complicated by stress or nonsteroidal anti-inflammatory drugs; 3 general anesthesia, post-surgery, or coma patients, to prevent acid reflux and aspiration pneumonia; 4 Combined with amoxicillin and clarithromycin, or with metronidazole and clarithromycin, it can effectively kill Helicobacter pylori (Hp).
Mechanisms of Action Omeprazole is a proton pump inhibitor which can specifically act on gastric parietal cell proton pump sites and transform into the active form of sulfonamide, then irreversibly binds to the proton pumps through disulfide bonds, generating a sulfonamide and proton pump compound (H + -K + -ATP), thereby inhibiting the enzymatic activity, preventing the H+ in parietal cells from being transported to the stomach cavity. It has a strong and persistent inhibitory role on gastric acid secretion caused by basal gastric acid and pentapeptide gastric acid secretions, greatly reducing gastric acid within the gastric juice. Rapid, reversible, and no H2 antagonist-induced psychiatric side effects.
Drug Interactions
Metronidazole and Hp-sensitive drugs (such as amoxicillin) acts in synergy with Omeprazole, improving the efficiency of Hp removal.
When combined with clarithromycin, the blood concentrations of both increase, increasing the incidence of adverse effects on the central nervous system and GI tract.
Omeprazole can improve the bioavailability of pancreatin, enhancing its efficacy. The two combined effectively treat obstructive diarrhea caused by cystic fibrosis of the pancreas and surgical diarrhea after extensive resection of the small intestine.
Combination with calcium antagonists slows down the clearance of both drugs, but without clinical significance.
Through CYP2C19 metabolism, extends the clearance of other enzymes such as diazepam, warfarin (R-warfarin), phenytoin, dicoumarol, nifedipine, antipyrine, and disulfiram in the liver. Omeprazole can lower acid, inhibiting activation of digoxin, reducing its efficacy. Digoxin dosages should be adjusted for a short period after discontinuation of use.
Combined with midazolam, lorazepam, or flurazepam, it can cause gait disorders, returning to normal after discontinuation of one drug.
Can inhibit the activation of prednisone, reducing its efficacy.
The acid suppression of Omeprazole can affect the absorption of iron salts.
Can reduce the absorption of Tetracycline, Ampicillin, Ketoconazole, and Iitraconazole, reducing blood plasma concentration, an effect related to the alkaline environment it causes.
Omeprazole inhibits the increase in gastric bacteria count from gastric acid, making nitrate carcinogenic; Combined with vitamins C or E, it may limit the formation of nitrous acid compounds.
No interaction with other antacids, but should not be combined.
Can influence blood plasma concentration of cyclosporine (positively or negatively), mechanism unknown.
No metabolic interaction with the following enzymes: caffeine, phenacetin, theophylline (CYP 1A2), S-warfarin, piroxicam, diclofenac and naproxen (CYP 2C9), lidocaine, quinidine, estradiol, erythromycin, budesonide (CYP 2D6), ethanol (CYP 2E1), lidocaine, quinidine, estradiol, erythromycin, and budesonide (CYP 3A).
Adverse reactions Omeprazole is well tolerated, and most adverse reactions are mild and reversible.
Cardiovascular: chest pain, palpitations, tachycardia or bradycardia, elevated blood pressure, and peripheral edema.
Nervous: headaches, dizziness, weakness, paresthesia, depression, anxiety, apathy, confusion, drowsiness, hallucinations, agitation, insomnia, nervousness, aggressive behavior, tremors, and peripheral neuritis, etc.
Metabolism and secretion: rare excess sweating, hyponatremia, and gynecomastia. Long-term use can lead to vitamin B12 deficiency and gastrinemia.
Muscular: rare joint pain, muscle pain, and muscle weakness.
Genitourinary: microscopic pyuria, protonuria, hematuria, frequent urination, urinary tract infection, interstitial nephritis, glucose in urine, and testicular pain.
Gastrointestinal: dry mouth, sitiophobia, nausea, vomiting, acid reflux, abdominal distension, abdominal pain, diarrhea, constipation, etc. Rare stomatitis, taste disorders, and gastrointestinal candidiasis. Some patients reported significantly increased concentration of live gastric bacteria after taking Omeprazole for 14 days (returning to normal 3 days after discontinuation). There are reports of atrophic gastritis after long-term use.
Liver: rare hepatitis or icteric hepatitis, liver necrosis, liver failure, and hepatic encephalopathy. Occasional mild elevation of alanine aminotransferase, aspartate aminotransferase, gamma-glutamyltransferase, alkaline phosphatase, and blood bilirubin was also observed.
Blood: hemolytic anemia was observed. Rare leukopenia, thrombocytopenia, agranulocytosis and various types of blood cell loss.
Skin: flush and dry skin. Rare dermatitis, pleomorphic erythema, Stevens-Johnson syndrome, toxic epithelial necrosis, and hair loss.
Allergic reactions: fever, rash, urticaria, itching, purpura, ecchymosis, angioneurotic edema, bronchospasm, and anaphylactic shock.
Eyes: rare blurred vision. One critically ill patient suffered from irreversible visual impairment after intravenous injection of Omeprazole at a high dosage.
12 Other: Animal experiments show that Omeprazole can cause the proliferation of the main endocrine cells in the fundus and body of stomach (intestinal chromaffin cells). Long-term use can also cause gastric cancers.
Preparation
When used for intravenous drip, solvents or diluents except for 0.9% sodium chloride or 5% glucose are prohibited. Combination with other drugs is also prohibited.
Gastric ulcer patients should exclude the possibility of gastric cancer during usage, because it may alleviate symptoms, thereby delaying diagnosis.
Note post-treatment; do not discontinue usage because of symptom alleviation.
Large doses of Omeprazole should not be used in the long term (except for gastrinoma) to prevent excessive inhibition of acid.
Use 100 ml of a dedicated solvent after injection of 40 mg, with injection time of 2.5-4 min - solvent should be used within 2 hours after preparation. Alternatively, use a 100 ml diluted intravenous drip lasting 20-30 minutes or longer after 0.9% sodium chloride or 5% glucose injection.
Omeprazole does not affect driving or machine operation.
Use with caution in the case of liver or renal dysfunction.
FDA pregnancy safety category C.
Chemical Properties White Crystalline Solid
Uses Binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative
Uses diuretic, sweetener, diagnostic aid
Uses A selective proton pump and CYP inhibitor
Uses Omeprazole Pellets are used in the treatment of Gastroesophageal reflux disease (GERD): A condition in which backward flow of acid from the stomach causes heartburn and injury of the food pipe (esophagus)
Definition ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.
Biological Activity H + ,K + -ATPase inhibitor (IC 50 = 5.8 μ M) that displays antisecretory and antiulcer activity. Inhibits gastric acid secretion (IC 50 = 0.16 μ M for histamine-induced acid formation) and reduces gastric lesion formation induced by a variety of ulcerative stimuli. Antibacteral against Helicobacter pylori in vitro . Also inhibits CYP2C19, CYP2C9 and CYP3A (K i values are 3.1, 40.1 and 84.4 μ M respectively) and blocks swelling-dependent chloride channels (ICIswell).
Omeprazole Preparation Products And Raw materials
Raw materials Chloroform-->3-Chloroperoxybenzoic acid-->o-Phenylenediamine-->3,5-Dimethyl-4-methoxy-2-pyridinemethanol-->Potassium ethylxanthate-->Benzimidazole-->5-Methoxy-2-mercaptobenzimidazole