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Omeprazole
Systematic (IUPAC) name
5-methoxy-2-[(4-methoxy-3,5-dimethyl- pyridin-2-yl)methylsulfinyl]-3H-benzimidazole
Identifiers
CAS number	73590-58-6
ATC code	A02BC01
PubChem	4594
DrugBank	APRD00446
Chemical data
Formula	C17H19N3O3S
Mol. mass	345.4 g/mol
Pharmacokinetic data
Bioavailability	35–60%
Metabolism	Hepatic (CYP2C19, CYP3A4)
Half life	1 - 1.2 hours
Excretion	80% Renal 20% Faecal
Therapeutic considerations
Pregnancy cat.	B3(AU) C(US) Image File history File links Acap. ... Image File history File links Omeprazole. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A02A Antacids A02AA Magnesium compounds A02AA01 Magnesium carbonate A02AA02 Magnesium oxide A02AA03 Magnesium peroxide A02AA04 Magnesium hydroxide A02AA05 Magnesium silicate A02AA10 Combinations A02AB Aluminium compounds A02AB01 Aluminium hydroxide A02AB02 Algeldrate A02AB03 Aluminium phosphate A02AB04 Dihydroxialumini sodium... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ present in vertebrates and some other animals. ... Cytochrome P450 2C19 (abbreviated CYP2C19), a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... Horse feces Feces, faeces, or fæces (see spelling differences) is a waste product from an animals digestive tract expelled through the anus (or cloaca) during defecation. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Legal status	Prescription Only (S4)(AU) P(UK) OTC(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... Over-the-counter (OTC) drugs are medicines that may be sold without a prescription, in contrast to prescription drugs. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Routes	Oral, IV

Omeprazole (INN) (IPA: [oʊˈmɛprəzoʊl]) is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD) and Zollinger-Ellison syndrome. It was first marketed by AstraZeneca as the magnesium salt omeprazole magnesium under the trade names Losec and Prilosec, and is now also available from generic manufacturers under various trade names. Omeprazole is one of the most widely prescribed drugs internationally and is available over the counter in some countries. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... Articles with similar titles include the NATO phonetic alphabet, which has also informally been called the “International Phonetic Alphabet”. For information on how to read IPA transcriptions of English words, see IPA chart for English. ... Proton pump inhibitors (or PPIs) are a group of drugs whose main action is pronounced and long-lasting reduction of gastric acid production. ... A benign gastric ulcer (from the antrum) of a gastrectomy specimen. ... Gastroesophageal Reflux Disease (GERD; or GORD when spelling Å“sophageal, the BrE form) is defined as chronic symptoms or mucosal damage produced by the abnormal reflux of gastric contents into the esophagus[1]. This is commonly due to transient or permanent changes in the barrier between the esophagus and the stomach. ... Zollinger-Ellison syndrome is a disorder where increased levels of the hormone gastrin are produced, causing the stomach to produce excess hydrochloric acid. ... AstraZeneca PLC (LSE: AZN, NYSE: AZN), is a large Anglo-Swedish pharmaceutical company formed on 6 April 1999 by the merger of Swedish Astra AB and British Zeneca Group. ... Over-the-counter substances, also abbreviated OTC, are drugs and other medical remedies that may be sold without a prescription and without a visit to a medical professional, in contrast to prescription only medicines (POM). ...

Facing the loss of patent protection and competition from generic manufacturers, AstraZeneca developed, launched, and heavily marketed esomeprazole (Nexium), a single enantiomer form of omeprazole. While it has been proven that only enantiomers in the "active" form are effective and others are not, due to the fact that the type of cytochrome which metabolizes the drug. Omeprazole is the racemate (S and R enantiomers) undergoing a chiral shift in vivo from the racemate to the S enantiomer (active form). This chiral shift is accomplished by the CYP 2C19 Cytochrome which is not found equally in all human populations. Those who do not metabolize the drug effectively are called "poor metabolizers" and their distribution is as follows: - Caucasians 8% - 12% - Asian 20% - South Pacific Islands 70% Esomeprazole is the S enantiomer in the pure form, and its effects on the proton pump is therefore equal in all these populations, eliminating the "poor metabolizer effect". Esomeprazole is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), GERD and Zollinger-Ellison syndrome. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ...

In 1990, at the request of the United States Food and Drug Administration (FDA), the brand name Losec was changed to Prilosec to avoid confusion with the diuretic Lasix (furosemide).^[1] Unfortunately, the new name has led to confusion between omeprazole (Prilosec) and fluoxetine (Prozac), an antidepressant.^[1] hi “FDA” redirects here. ... A diuretic (colloquially called a water pill) is any drug or herb that elevates the rate of bodily urine excretion (diuresis). ... Furosemide (INN) or frusemide (former BAN) is a loop diuretic used in the treatment of congestive heart failure and edema. ... Fluoxetine pills. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a psychiatric medication taken to alleviate clinical depression or dysthymia (milder depression). ...

Clinical use

Main article: Proton pump inhibitor

Proton pump inhibitors (or PPIs) are a group of drugs whose main action is pronounced and long-lasting reduction of gastric acid production. ...

Use in Helicobacter pylori eradication

Omeprazole is combined with the antibiotics clarithromycin and amoxicillin (or metronidazole in penicillin-hypersensitive patients) in the one week eradication triple therapy for Helicobacter pylori. Infection by H. pylori is the causative factor in the majority of peptic and duodenal ulcers. ^{[citation needed]} Clarithromycin is a macrolide antibiotic used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydia pneumoniae or TWAR), skin and skin structure infections, and, in HIV and AIDS patients to prevent, and to treat, disseminated Mycobacterium avium complex (MAC). ... Amoxicillin (INN) or amoxycillin (former BAN) is a moderate-spectrum β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. ... Metronidazole (INN) (IPA: ) is a nitroimidazole anti-infective drug used mainly in the treatment of infections caused by susceptible organisms, particularly anaerobic bacteria and protozoa. ... Binomial name Helicobacter pylori ((Marshall 1985) Goodwin 1989) Helicobacter pylori is a helical shaped Gram-negative bacterium that colonises the mucus layer of gastric epithelium in the stomach, and also the duodenum when it has undergone gastric metaplasia. ... A benign gastric ulcer (from the antrum) of a gastrectomy specimen. ...

Dosage forms

Package of Losec (Omeprazole) 20mg, purchased in Hong Kong

Omeprazole 20mg, From U.K.

Omeprazole 10mg, From U.K.

Omeprazole is available as tablets and capsules (containing omeprazole or omeprazole magnesium) in strengths of 10 mg, 20 mg, and in some markets 40 mg; and as a powder (omeprazole sodium) for intravenous injection. Most oral omeprazole preparations are enteric-coated, due to the rapid degradation of the drug in the acidic conditions of the stomach. This is most commonly achieved by formulating enteric-coated granules within capsules, enteric-coated tablets, and the multiple-unit pellet system. Image File history File linksMetadata Download high-resolution version (1944x2592, 1714 KB) Package of Losec (Omeprazole) 20mg, purchased in Hong Kong I, the creator of this work, hereby release it into the public domain. ... Image File history File linksMetadata Download high-resolution version (1944x2592, 1714 KB) Package of Losec (Omeprazole) 20mg, purchased in Hong Kong I, the creator of this work, hereby release it into the public domain. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2048 × 1536 pixel, file size: 848 KB, MIME type: image/jpeg) Omeprazole 20mg (UK) I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2048 × 1536 pixel, file size: 848 KB, MIME type: image/jpeg) Omeprazole 20mg (UK) I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2048 × 1536 pixel, file size: 799 KB, MIME type: image/jpeg) Omeprazole 10mg from UK I, the copyright holder of this work, hereby release it into the public domain. ... Image File history File links Metadata Size of this preview: 800 × 600 pixelsFull resolution (2048 × 1536 pixel, file size: 799 KB, MIME type: image/jpeg) Omeprazole 10mg from UK I, the copyright holder of this work, hereby release it into the public domain. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... An enteric coating is a barrier applied to oral medication that controls the location in the digestive system where it is absorbed. ... For other uses, see Acid (disambiguation). ... In anatomy, the stomach is a bean-shaped hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication. ...

It is also available for use in injectable form (I.V.) in Europe, but not in the U.S. 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.

Losec is manufactured by AstraZeneca, Södertälje, Sweden. AstraZeneca PLC (LSE: AZN, NYSE: AZN), is a large Anglo-Swedish pharmaceutical company formed on 6 April 1999 by the merger of Swedish Astra AB and British Zeneca Group. ...

Multiple unit pellet system

Omeprazole tablets manufactured by AstraZeneca (notably Losec/Prilosec) are formulated as a "multiple unit pellet system" (MUPS). Essentially, the tablet consists of extremely small enteric-coated granules (pellets) of the omeprazole formulation inside an outer shell. When the tablet is immersed in an aqueous solution, as happens when the tablet reaches the stomach, water enters the tablet by osmosis. The contents swell from water absorption causing the shell to burst, releasing the enteric-coated granules. For most patients, the multiple-unit pellet system is of no advantage over conventional enteric-coated preparations. Patients for which the formulation is of benefit include those requiring nasogastric tube feeding and those with difficulty swallowing (dysphagia). This article does not cite any references or sources. ... Osmosis is the net movement of water across a partially permeable membrane from a region of high solvent potential to an area of low solvent potential, up a solute concentration gradient. ... A nasogastric tube (NG tube) is a plastic tube, inserted into a nostril through the nose, into the throat, down the oesophagus and into the stomach. ... Dysphagia () is a medical term defined as difficulty swallowing. ...

The granules are manufactured in a fluid air bed system. Sugar spheres in suspension are sequentially sprayed with aqueous suspensions of omeprazole, a protective layer, an enteric coating and an outer layer to reduce granule aggregation. The granules are mixed with other excipients and compressed into tablets. Finally, the tablets are film-coated to improve the stability and appearance of the preparation. It has been suggested that this article or section be merged into Mixture. ... An excipient is an inactive substance used as a vehicle for medication, or an active ingredient. ...

Immediate release formulation

In June 2004 the FDA approved an immediate release preparation of omeprazole/sodium bicarbonate that does not require an enteric coating. This preparation employs sodium bicarbonate as a buffer to protect omeprazole from gastric acid degradation. This allows for the production of chewable tablets. This combination preparation is marketed in the United States by Santarus under the trade name Zegerid. Zegerid is marketed as capsules, chewable tablets, and powder for oral suspension. Zegerid is most useful for those patients who suffer from nocturnal acid breakthrough (NAB) or those patients who desire immediate relief. Sodium bicarbonate is the chemical compound with the formula NaHCO3. ...

Side effects

As with all proton pump inhibitors, omeprazole is generally well tolerated, however it must be avoided by anyone with a suspicion of lesions or bleeding ulcers. Some of the most frequent side effects of omeprazole (experienced by over 1% of those taking the drug) are headache, diarrhea, abdominal pain, nausea and dizziness, although in clinical trials the incidence of these effects with omeprazole was mostly comparable to that found with placebo.^[2] An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... A headache (cephalalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... For other uses, see Nausea (disambiguation). ... // Pre-syncope is a sensation of feeling faint. ... In health care, including medicine, a clinical trial (synonyms: clinical studies, research protocols, medical research) is a process in which a medicine or other medical treatment is tested for its safety and effectiveness, often in comparison to existing treatments. ... For other uses, see Placebo (disambiguation). ...

Proton pump inhibitors may be associated with a greater risk of hip fractures ^[3] and clostridium difficile diarrhoea.^[4] Binomial name Hall & OToole, 1935 Clostridium difficile or CDF/cdf (commonly mistaken  , alternatively and correctly pronounced ) (also referred to as C. diff or C-diff) is a species of bacteria of the genus Clostridium which are gram-positive, anaerobic, spore-forming rods (bacillus). ...

Absorption and distribution

The absorption of omeprazole takes place in the small intestine and is usually completed within 3-6 hours. The systemic bioavailability of omeprazole after repeated dose is about 60%. Concomitant intake of food has no influence on the bioavailability. Plasma protein binding is about 95%. In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ...

Metabolism and excretion

Omeprazole is completely metabolised by the cytochrome P450 system, mainly in the liver. Identified metabolites are the sulphone, the sulphide and hydroxy-omeprazole, which exert no significant effect on the 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. Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... In chemistry, a sulfide (sulphide in British and Canadian English) is a combination of sulfur with an oxidation number of -2, with another chemical element or a radical thereof. ...

Brand names

Zegerid
Prilosec, Losec, Prilosec OTC, Omez
Antra® in Italy
Nexium (esomeprazole, a S-enantiomer of omeprazole)
Ozid® in Indonesia )
OMEZ (India) Esomeprazole is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), GERD and Zollinger-Ellison syndrome. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ...

OCID QRS Zydus cadila. India.

References

1. ^ ^{a b} Farley D. Making It Easier to Read Prescriptions. FDA Consumer magazine. July-August 1995. URL: http://www.fda.gov/fdac/features/695_prescrip.html. Accessed on: June 11, 2006.
2. ^ Prilosec Side Effects & Drug Interactions. RxList.com (2007). Retrieved on 2007-06-16.
3. ^ Yang YX, Lewis JD, Epstein S, Metz DC (2006). "Long-term Proton Pump Inhibitor Therapy and Risk of Hip Fracture". JAMA 296 (24): 2947-53. DOI:10.1001/jama.296.24.2947. PMID 17190895. 
4. ^ Proton pump inhibitors and Clostridium difficile. Bandolier (2003). Retrieved on 2007-07-13.

Ocid.Zydus Cadila. Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... is the 167th day of the year (168th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... is the 194th day of the year (195th in leap years) in the Gregorian calendar. ...

External links

• Detailed Prilosec Consumer Information: Uses, Precautions, Side Effects