AstraZeneca has also developed esomeprazole (Nexium) which is a eutomer, purely the ( S )-enantiomer, rather than a racemate like omeprazole.
Drugs that depend on an acidic stomach environment (such as ketoconazole or atazanavir ) may be poorly absorbed, whereas acid-labile antibiotics (such as erythromycin which is a very strong CYP3A4 inhibitor) may be absorbed to a greater extent than normal due to the more alkaline environment of the stomach.
Omeprazole is also available as an oral suspension of enteric-coated beads in the UK as an unlicensed product. Oral suspensions are predominantly used for children, but can also be used by those with difficulty swallowing or those using a feeding tube.
This chiral shift is accomplished by the CYP2C19 isozyme of cytochrome P450, which is not found equally in all human populations. Omeprazole undergoes a chiral shift in vivo which converts the inactive ( R )-enantiomer to the active ( S )-enantiomer, doubling the concentration of the active form. The proportion of the poor metabolizer phenotype varies widely between populations, from 2.0–2.5% in African Americans and white Americans to >20% in Asians; several pharmacogenomics studies have suggested that PPI treatment should be tailored according to CYP2C19 metabolism status. Those who do not metabolize the drug effectively are called "poor metabolizers".
The injection pack is a combination pack consisting of a vial and a separate ampule of reconstituting solution. Each 10-ml clear glass vial contains a white to off-white lyophilised powder consisting of omeprazole sodium 42.6 mg, equivalent to 40 mg of omeprazole. It is also available for use in injectable form (IV) in Europe, but not in the U.S.
Omeprazole contains a tricoordinated sulfinyl sulfur in a pyramidal structure and therefore can exist as either the ( S )- or ( R )- enantiomers. Omeprazole is a racemate, an equal mixture of the two. In the acidic conditions of the canaliculi of parietal cells, both enantiomers are converted to chiral products ( sulfenic acid and sulfenamide configurations) which react with a cysteine group in H+/K+ ATPase, thereby inhibiting the ability of the parietal cells to produce gastric acid.
Omeprazole is also a competitive inhibitor of p-glycoprotein, as are other PPIs.
When omeprazole is stopped, baseline stomach acid secretory activity returns after 3 to 5 days. The inhibitory effect of omeprazole on acid secretion will plateau after 4 days of repeated daily dosing. The maximum effect occurs within 2 hours. The inhibitory effect of omeprazole occurs within 1 hour after oral administration. The duration of inhibition is up to 72 hours.
pylori infection can be completed by taking a triple therapy combination of omeprazole, amoxicillin, and clarithromycin for 7–14 days. Treatment of H. Peptic ulcers may be treated with omeprazole. Amoxicillin may be replaced with metronidazole in patients who are allergic to penicillin.
This interaction is possible because omeprazole is an inhibitor of the enzymes CYP2C19 and CYP3A4. Inhibition of CYP2C19 may block the activation of clopidogrel, which could reduce its effects. Clopidogrel is an inactive prodrug that partially depends on CYP2C19 for conversion to its active form.
Concern has been expressed regarding vitamin B 12 and iron malabsorption, but effects seem to be clinically insignificant, especially when supplement therapy is provided.
Because this enzyme system is regarded as the acid (proton, or H+) pump within the gastric mucosa, omeprazole inhibits the final step of acid production. Omeprazole is a selective and irreversible proton pump inhibitor. It suppresses stomach acid secretion by specific inhibition of the H+/K+-ATPase system found at the secretory surface of gastric parietal cells.
Additionally, most sources recommend that after taking omeprazole, at least 30 minutes should be allowed to elapse before eating (at least 60 minutes for immediate-release omeprazole plus sodium bicarbonate products, such as Zegerid), though some sources say that with delayed-release forms of omeprazole, waiting before eating after taking the medication is not necessary. Omeprazole, as well as other PPIs, are only effective on active H+/K+-ATPase pumps. For this reason, patients should be advised to take omeprazole with a glass of water on an empty stomach. These pumps are stimulated in the presence of food to aid in digestion.
However, the most significant major drug interaction concern is the decreased activation of clopidogrel when taken together with omeprazole. Although still controversial, this may increase the risk of stroke or heart attack in people taking clopidogrel to prevent these events.
Proton-pump inhibitors like omeprazole have been found to increase the plasma concentrations of methotrexate.
The most frequent significant adverse effects occurring in at least 1% of patients include:
St. John's wort ( Hypericum perforatum ) and Gingko biloba significantly reduce plasma concentrations of omeprazole through induction of CYP3A4 and CYP2C19.
Important drug interactions are rare.
When Prilosec's U.S. patent expired in April 2001, AstraZeneca introduced esomeprazole (Nexium) as a patented replacement drug. Many companies introduced generics as AstraZeneca's patents expired worldwide, which are available under many brand names.
Since their introduction, proton-pump inhibitors (PPIs, especially omeprazole) have also been associated with several cases of acute interstitial nephritis, an inflammation of the kidneys that often occurs as an adverse drug reaction.
This is most commonly achieved by formulating enteric-coated granules within capsules, enteric-coated tablets, and the multiple-unit pellet system (MUPS). Most oral omeprazole preparations are enteric-coated, due to the rapid degradation of the drug in the acidic conditions of the stomach. An immediate release formulation was approved by the FDA in the United States, which does not require enteric coating. Omeprazole is available as tablets and capsules (containing omeprazole or omeprazole magnesium) in strengths of 10, 20, 40, and in some markets 80 mg; and as a powder (omeprazole sodium) for intravenous injection.
Other significant concerns related to adverse effects are:
Omeprazole at normal doses is likely safe during breastfeeding.
Omeprazole is a proton-pump inhibitor and as such blocks the release of stomach acid. Common side effects include nausea, vomiting, headaches, and increased intestinal gas. It is unclear if it is safe for use in pregnancy. Serious side effects may include Clostridium difficile colitis, an increased risk of pneumonia, an increased risk of bone fractures, and the potential of masking stomach cancer.
Omeprazole can be used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcers, erosive esophagitis, and Zollinger-Ellison syndrome.
Epidemiological data do not show an increased risk of major birth defects after maternal use of omeprazole during pregnancy.
No association is seen between PPI use and cancer, but use of PPIs may mask gastric cancers or other serious gastric problems and physicians should be aware of this effect. Long-term use of PPIs is strongly associated with the development of benign polyps from fundic glands (which is distinct from fundic gland polyposis ); these polyps do not cause cancer and resolve when PPIs are discontinued.
The wholesale cost in the developing world as of 2014 is US$ 0.01 to US$0.07 per dose. In the United States it costs on average US$0.50 per pill. It is available as a generic medication. Omeprazole was discovered in 1979. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.
However, the pharmacokinetics of omeprazole molecule strongly suggest the safety of omeprazole use during breastfeeding:. No clinical trials have deeply evaluated the potential consequences of the use of omeprazole in breastfeeding.
the total effect over time of a given dose). Almost all benzodiazepines are metabolised by the CYP3A4 and CYP2D6 pathway, and inhibition of these enzymes results in a higher AUC (i.e. The concentrations of these drugs may increase if they are used concomitantly with omeprazole. Other examples of drugs dependent on CYP3A4 for their metabolism are escitalopram, warfarin, oxycodone, tramadol, and oxymorphone.
The new name led to confusion between omeprazole (Prilosec) and fluoxetine (Prozac), an antidepressant. Food and Drug Administration, the brand name Losec was changed to Prilosec to avoid confusion with the diuretic Lasix ( furosemide ). In 1990, at the request of the U.S. Omeprazole was first marketed in the United States in 1989 by Astra AB, now AstraZeneca, under the brand name Losec.
The absorption of omeprazole takes place in the small intestine and is usually completed within 3 to 6 hours. The systemic bioavailability of omeprazole after repeated dose is about 60%.
Omeprazole also inhibits both basal and stimulated acid secretion irrespective of the stimulus.
Omeprazole is compley metabolized by the cytochrome P450 system, mainly in the liver. Identified metabolites are the sulfone, the sulfide, and hydroxy-omeprazole, which exert no significant effect on acid secretion. About 80% of an orally given dose is excreted as metabolites in the urine, and the remainder is found in the feces, primarily originating from bile secretion.
It can be taken by mouth or injected into a vein. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. Omeprazole, sold under the brand names Prilosec and Losec among others, is a medication used in the treatment of gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome.
Plasma omeprazole concentrations are usually in a range of 0.2–1.2 mg/l in persons receiving the drug therapeutically by the oral route and 1–6 mg/l in victims of acute overdose. Omeprazole may be quantified in plasma or serum to monitor therapy or to confirm a diagnosis of poisoning in hospitalized patients. Enantiomeric chromatographic methods are available to distinguish esomeprazole from racemic omeprazole.Prilosec