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73590-58-6

73590-58-6 Structure

73590-58-6 Structure
IdentificationMore
[Name]

Omeprazole
[CAS]

73590-58-6
[Synonyms]

2-[(4-METHOXY-3,5-DIMETHYLPYRID-2-YL)-METHYLSULFO]-5-METHOXYBENZIMIDAZOLE
5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]SULFINYL]-1H-BENZIMIDAZOLE
5-METHOXY-2[(4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYLSULFINYL]-1H-BENZIMIDAZOLE
5-methoxy-2-((s)-((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl)-1h-benzimidazole
6-methoxy-2-[(r)-(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-1h-benzoimidazole
ANTRA
ESOMEPRAZOLE
GASTROGARD
GASTROLOC
H 168/68
LOSEC
MEPRAL
MOPRAL
OMEPRAL
OMEPRAZOLE
PRILOSEC
R-(+)-OMEPRAZOLE
(S)-OMEPRAZOLE
ZOLTUM
1h-benzimidazole,5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulf
[Molecular Formula]

C17H19N3O3S
[MDL Number]

MFCD00083192
[Molecular Weight]

345.42
[MOL File]

73590-58-6.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[mp ]

156°C
[storage temp. ]

2-8°C
[solubility ]

H2O: 0.5 mg/mL
[form ]

solid
[color ]

white
[Stability:]

Stable, but hygroscopic and photosensitive. Incompatible with strong oxidizing agents. Store in the dark.
[Usage]

Binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative
[Merck ]

6845
[CAS DataBase Reference]

73590-58-6(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

2
[RTECS ]

DD9087000
[HS Code ]

29333990
[Hazardous Substances Data]

73590-58-6(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Chloroform-->3-Chloroperoxybenzoic acid-->o-Phenylenediamine-->3,5-Dimethyl-4-methoxy-2-pyridinemethanol-->Potassium ethylxanthate-->Benzimidazole-->5-Methoxy-2-mercaptobenzimidazole
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

5-Methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-3H-benzoimidazole(73590-58-6).msds
Questions And AnswerBack Directory
[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.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

73590-58-6(sigmaaldrich)
[TCI AMERICA]

Omeprazole,>98.0%(LC)(T)(73590-58-6)
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