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O104 Sigma

Omeprazole

solid

Synonym: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, Antra, Losec

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Description

Biochem/physiol Actions

Binds covalently to proton pump; inhibits gastric secretion.

Caution

Hygroscopic, photosensitive

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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DISCOVER Bioactive Small Molecules

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
2
RTECS 
DD9087000

Protocols & Articles

Articles

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Peer-Reviewed Papers

References

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Effect of inhibitors of Na+/H+-exchange and gastric H+/K+ ATPase on cell volume intracellular pH and migration of human polymorphonuclear leucocytes. Ritter, M. et al. Br. J. Pharmacol. 124, 627-638, (1998)

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Different biochemical modes of action of two irreversible H+K (+)-ATPase inhibitors omeprazole and E3810. Morii, M., et al. J. Biol. Chem. 268, 21553, (1993)

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Identification of amino acid residues in the ligand-binding domain of the aryl hydrocarbon receptor causing the species-specific response to omeprazole: possible determinants for binding putative endogenous ligands. Shiizaki K, Ohsako S, Kawanishi M, et al. Mol. Pharmacol. 85(2), 279-89, (2014)

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Electrochemical incineration of omeprazole in neutral aqueous medium using a platinum or boron-doped diamond anode: degradation kinetics and oxidation products. Cavalcanti EB, Garcia-Segura S, Centellas F, et al. Water Res. 47(5), 1803-15, (2013)

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Aberrant autolysosomal regulation is linked to the induction of embryonic senescence: differential roles of Beclin 1 and p53 in vertebrate Spns1 deficiency. Sasaki T, Lian S, Qi J, et al. PLoS Genet. 10(6), e1004409, (2014)

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Hydroxylation index of omeprazole in relation to CYP2C19 polymorphism and sex in a healthy Iranian population. Payan M, Rouini MR, Tajik N, et al. Daru 22, 81, (2014)

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Seminal Helicobacter pylori treatment improves sperm motility in infertile asthenozoospermic men. El-Garem Y, El-Sawy M, and Mostafa T Urology 84(6), 1347-50, (2014)

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Helicobacter pylori first-line and rescue treatments in the presence of penicillin allergy. Gisbert JP, Barrio J, Modolell I, et al. Dig. Dis. Sci. 60(2), 458-64, (2015)

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Discussion. Surgery 156(4), 978, (2014)

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[Congenital chloride diarrhea mimicking meconium ileus in newborn]. Krzemień G, Szmigielska A, Jankowska K, et al. Med. Wieku Rozwoj. 17(4), 320-3, (2013)

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[Influence of oxidative stress on the level of genes expression Tgfb1 and Hgf in rat liver upon long-term gastric hypochlorhydria and administration of multiprobiotic Symbiter]. Dvorshchenko KO, Bernyk OO, Dranytsyna AS, et al. Ukr. Biokhim. Zh. 85(5), 114-23, (2013)

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Expression comparison of azithromycin and clarithromycin in triple-therapy regimens for eradication of Helicobacter pylori in hemodialysis patients. Vafaeimanesh J, Jalalzadeh M, and Nazarian M Saudi J. Kidney Dis. Transpl. 25(1), 53-7, (2014)

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[It is possible to reduce drug-drug interactions. Interactions were corrected frequently by patient-specific letters to general practitioners]. Cronberg O, Nordquist C, and Quittenbaum S Lakartidningen. 110(48), 2176-7, (2013)

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PA tablets: investigational compounds combining aspirin and omeprazole for cardioprotection. Bliden KP, Brener M, Gesheff MG, et al. Future Cardiol. 9(6), 785-97, (2013)

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Increasing primary antibiotic resistance and ethnic differences in eradication rates of Helicobacter pylori infection in New Zealand--a new look at an old enemy. Hsiang J, Selvaratnam S, Taylor S, et al. N. Z. Med. J. 126(1384), 64-76, (2013)

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[HP eradication prevents recurrent hemorrhages caused by acetylsalicylic acid]. Labenz J MMW Fortschr. Med. 155(12), 31, (2013)

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[Laryngopharyngeal reflux as a possible cause of adenoiditis in adult patients]. Angotoeva IB and Muldasheva AA Vestn. Otorinolaringol. (3), 52-5, (2013)

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[Stress-responsive systems in the rat pancreas upon long-term gastric hypochlorhydria and administration of multiprobiotic "Symbiter"]. Dvorshchenko KO, Vakal SIe, Dranytsyna AS, et al. Ukr. Biokhim. Zh. 85(2), 68-77, (2013)

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[The interferon production by rat spleen and thymus lymphocytes in condititons of hypoacidity]. Kompanets' IV, Korotkyĭ OH, Nikols'ka VV, et al. Fiziol. Zh. 59(1), 84-8, (2013)

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Bismuth + metronidazole + tetracycline. Why risk adding bismuth? Prescrire Int. 22(137), 89-92, (2013)

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Pharmacokinetics of a new immediate-release compound omeprazole capsule and its comparison with the enteric-coated formulation under fasting and fed conditions. Liu Z, Ding L, Zhong S, et al. Drug Res. (Stuttg.) 63(7), 370-5, (2013)

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Common medications among dental outpatients: considerations in general dental practice. Cutfield NI and Tong DC N. Z. Dent. J. 108(4), 140-7, (2012)

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[The role of gastric pH and tissue hypoxia in formation of gastroduodenal zone mucose changes in heartsurgical patients]. Sorokina EA, Fokin AA, Akhmedov VA, et al. Eksp. Klin. Gastroenterol. (5), 14-21, (2012)

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[Using ursodez in the treatment of refractory form of gastroesophageal reflux disease]. Osadchuk AM and Davydkin IL Eksp. Klin. Gastroenterol. (4), 74-5, (2012)

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[Efficacy of esomeprazole compared with omeprazole in reflux esophagitis patients -a phase III, multicenter, randomized, double-blind, parallel-group trial-]. Kinoshita Y, Miwa H, and Kasugai K Nihon Shokakibyo Gakkai Zasshi 110(2), 234-42, (2013)

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[Comment of the Delphi Care editors on Critical evaluation of interaction screening software available in pharmacies]. Duh D and Tanret I J. Pharm. Belg. (4), 14-5, (2012)

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[Efficacy and safety of OTC omeprazole]. Labenz J and Willmer C MMW Fortschr. Med. 154 Suppl 4, 110-4, (2012)

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Crying and spilling--time to stop the overmedicalisation of normal infant behaviour. Hudson B, Alderton A, Doocey C, et al. N. Z. Med. J. 125(1367), 119-26, (2012)

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A case of subglottic and diffuse tracheal stenoses appearing responsive to macrolide therapy. Sanders JG and Jean-Louis MF N. Z. Med. J. 125(1366), 68-73, (2012)

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[Pharmacy compounding of an omeprazole suspension]. Van Der Straeten F, Al-Afandi A, De Paepe K, et al. J. Pharm. Belg. (2), 54-63, (2009)

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Towards evidence based emergency medicine: best BETs from the Manchester Royal Infirmary. BET 2. Use of intravenous omeprazole in gastrointestinal patients before endoscopy. Tai CK Emerg. Med. J. 25(11), 765, (2008)

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[Recent topics on important drugs for H. pylori eradication: Omeprazole]. Kataoka H, Jho T, and Itoh M Nihon Rinsho. 63 Suppl 11, 333-7, (2005)

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Omeprazole/Antacid-powder suspension-Santarus: omeprazole/sodium bicarbonate powder-Santarus, SAN 05. Drugs R. D. 5(6), 349-50, (2004)

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OTC omeprazole for your heartburn--enormous value-for-money opportunity. Curtiss FR J. Manag. Care Pharm. 10(5), 458-60, (2004)

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Omeprazole/antacid-powder suspension--Santarus: Acitrel, Rapinex Powder for oral suspension, SAN 05. Drugs R. D. 5(4), 234-5, (2004)

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[A case of gastric fundic polyps during long-term treatment of reflux esophagitis with omeprazole]. Yamamoto T, Matsumoto J, Kosaihira T, et al. Nihon Shokakibyo Gakkai Zasshi 100(4), 421-5, (2003)

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[Proton pump inhibitors: Omeprazole]. Iwasaki A Nihon Rinsho. 60 Suppl 2, 633-9, (2002)

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A proton-pump inhibitor expedition: the case histories of omeprazole and esomeprazole. Olbe L, Carlsson E, and Lindberg P Nat. Rev. Drug Discov. 2(2), 132-9, (2003)

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Randomised clinical trial comparing sequential and concomitant therapies for Helicobacter pylori eradication in routine clinical practice. McNicholl AG, Marin AC, Molina-Infante J, et al. Gut 63(2), 244-9, (2014)

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Mucosal protective agents prevent exacerbation of NSAID-induced small intestinal lesions caused by antisecretory drugs in rats. Satoh H, Amagase K, and Takeuchi K J. Pharmacol. Exp. Ther. 348(2), 227-35, (2014)

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Acute interstitial nephritis due to omeprazole. Myers RP, McLaughlin K, and Hollomby DJ Am. J. Gastroenterol. 96(12), 3428-31, (2001)

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Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Mishra V, Agrawal M, Onasanwo SA, et al. Phytomedicine 20(6), 506-11, (2013)

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Proton pump inhibitors induce changes in colonocyte gene expression that may affect Clostridium difficile infection. Hegarty JP, Sangster W, Harris LR, et al. Surgery 156(4), 972-8, (2014)

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Twice a day quadruple therapy for the first-line treatment of Helicobacter pylori in an area with a high prevalence of background antibiotic resistance. Köksal AS, Onder FO, Torun S, et al. Acta Gastroenterol. Belg. 76(1), 34-7, (2013)

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Review article: pharmacology of esomeprazole and comparisons with omeprazole. Dent J Aliment. Pharmacol. Ther. 17 Suppl 1, 5-9, (2003)

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Evaluation of the effect of TM208 on the activity of five cytochrome P450 enzymes using on-line solid-phase extraction HPLC-DAD: a cocktail approach. Lin W, Zhang J, Ling X, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 923-924, 29-36, (2013)

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The influence of the CYP2C19*10 allele on clopidogrel activation and CYP2C19*2 genotyping. Langaee TY, Zhu HJ, Wang X, et al. Pharmacogenet. Genomics 24(8), 381-6, (2014)

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Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity. El-Nezhawy AO, Biuomy AR, Hassan FS, et al. Bioorg. Med. Chem. 21(7), 1661-70, (2013)

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In oesophageal squamous cells exposed to acidic bile salt medium, omeprazole inhibits IL-8 expression through effects on nuclear factor-κB and activator protein-1. Huo X, Zhang X, Yu C, et al. Gut 63(7), 1042-52, (2014)

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Analytical methodologies for the determination of omeprazole: an overview. Espinosa Bosch M, Ruiz Sánchez AJ, Sánchez Rojas F, et al. J. Pharm. Biomed. Anal. 44(4), 831-44, (2007)

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Inhibition of TNF-α, and NF-κB and JNK pathways accounts for the prophylactic action of the natural phenolic, allylpyrocatechol against indomethacin gastropathy. Yadav SK, Adhikary B, Bandyopadhyay SK, et al. Biochim. Biophys. Acta 1830(6), 3776-86, (2013)

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Spaced administration of PA32540 and clopidogrel results in greater platelet inhibition than synchronous administration of enteric-coated aspirin and enteric-coated omeprazole and clopidogrel. Gurbel PA, Bliden KP, Fort JG, et al. Am. Heart J. 165(2), 176-82, (2013)

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The H+/K+-ATPase inhibitory activities of Trametenolic acid B from Trametes lactinea (Berk.) Pat, and its effects on gastric cancer cells. Zhang Q, Huang N, Wang J, et al. Fitoterapia 89, 210-7, (2013)

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Chronological effects of rifampicin discontinuation on cytochrome P450 activity in healthy Japanese volunteers, using the cocktail method. Inui N, Akamatsu T, Uchida S, et al. Clin. Pharmacol. Ther. 94(6), 702-8, (2013)

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Review of immediate-release omeprazole for the treatment of gastric acid-related disorders. Castell D Expert Opin. Pharmacother. 6(14), 2501-10, (2005)

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Anti-inflammatory, gastroprotective and anti-ulcerogenic effects of red algae Gracilaria changii (Gracilariales, Rhodophyta) extract. Shu MH, Appleton D, Zandi K, et al. BMC Complement Altern. Med. 13, 61, (2013)

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Oral proton pump inhibitors disrupt horizontal cell-cone feedback and enhance visual hallucinations in macular degeneration patients. Hanneken AM, Babai N, and Thoreson WB Invest. Ophthalmol. Vis. Sci. 54(2), 1485-9, (2013)

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Slow, spontaneous degradation of lansoprazole, omeprazole and pantoprazole tablets: isolation and structural characterization of the toxic antioxidants 3H-benzimidazole-2-thiones. Rajab A, Touma M, Rudler H, et al. Pharmazie 68(9), 749-54, (2013)

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Pylera plus omeprazole: quadruple treatment for Helicobacter pylori. Baker DE Rev. Gastroenterol. Disord. 8(1), 33-41, (2008)

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Non-steroidal anti-inflammatory drugs and gastroprotection with proton pump inhibitors: a focus on ketoprofen/omeprazole. Gigante A and Tagarro I Clin. Drug Investig. 32(4), 221-33, (2012)

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Effects of commonly used medications on bone tissue mineralisation in SaOS-2 human bone cell line: an in vitro study. Salai M, Somjen D, Gigi R, et al. Bone Joint J. 95-B(11), 1575-80, (2013)

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Effects of Helicobacter pylori treatment on gastric cancer incidence and mortality in subgroups. Li WQ, Ma JL, Zhang L, et al. J. Natl. Cancer Inst. 106(7), doi:10.1093/jnci/dju116, (2014)

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Is omeprazole helpful in the management of children with reflux oesophagitis? Varughese LA and Mazur LJ Arch. Dis. Child. 87(1), 78-80, (2002)

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Risk of adverse cardiovascular outcomes and all-cause mortality associated with concomitant use of clopidogrel and proton pump inhibitors in elderly patients. Mahabaleshwarkar RK, Yang Y, Datar MV, et al. Curr. Med. Res. Opin. 29(4), 315-23, (2013)

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Development and evaluation of omeprazole pellets fabricated by sieving-spheronization and extrusion - spheronization process. Karim S, Baie SH, Hay YK, et al. Pak. J. Pharm. Sci. 27(3), 425-38, (2014)

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Pharmacokinetics of intravenous omeprazole in critically ill paediatric patients. Solana MJ and López-Herce J Eur. J. Clin. Pharmacol. 66(4), 323-30, (2010)

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Incidence of bacteremia following upper gastrointestinal endoscopy and biopsy in healthy dogs before, during, and after treatment with omeprazole. Jones KR, Maddox CW, Ridgway MD, et al. Am. J. Vet. Res. 74(2), 239-42, (2013)

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Toxic epidermal necrolysis and neutropaenia: complications of omeprazole. Thakor AS, Burke A, Handfield-Jones S, et al. Australas. J. Dermatol. 50(3), 207-10, (2009)

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Anaphylactic reaction after the concomitant intravenous administration of corticosteroids and gastroprotective drugs: two case reports. Ventura MT, Buquicchio R, Cecere R, et al. J. Biol. Regul. Homeost. Agents 27(2), 589-94, (2013)

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[Acute interstitial nephritis associated with omeprazole therapy]. Torregrosa E, Rovira RE, Calvo C, et al. Nefrologia 24 Suppl 3, 61-3, (2004)

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A massive occult pericardial effusion in an athletic young male. Thompson MH, Corbett GD, Cherian A, et al. J. R. Army Med. Corps 159(2), 126-8, (2013)

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Healing effect of hydro-alcoholic extract of Ephedra pachyclada Boiss. in experimental gastric ulcer in rat. Pirbalouti AG, Amirmohammadi M, Azizi S, et al. Acta Pol. Pharm. 70(6), 1003-9, (2013)

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[Jejunal intussusceptions as a lead point ectopic pancreatic tissue in a 1-year-old male. Case report]. Galván-Montaño A, Suárez-Roa Mde L, and Estrada-Hernández Mdel R Cir. Cir. 80(6), 546-9, (2012)

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Effect of proton pump inhibitors on the secretion of bicarbonates and pepsinogen induced by chemical stimulation of the gastric mucosa. Zolotarev VA and Khropycheva RP Bull. Exp. Biol. Med. 154(4), 415-8, (2013)

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Gastric acid-dependent diseases: a twentieth-century revolution. Sachs G, Shin JM, Munson K, et al. Dig. Dis. Sci. 59(7), 1358-69, (2014)

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