File:Omeprazole_enantiomers_labelled.svg · Wikimedia Commons · See Wikimedia Commons
omeprazole
Sign in to saveAlso known as H 168/68, Losec®, Prilosec®, OMEP, Omeprazolum, Omeprazol, Losec
Omeprazole, sold under the brand names Prilosec and Losec among others, is a medication used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. Omeprazole is a proton-pump inhibitor (PPI) and its effectiveness is similar to that of other PPIs. It can be taken by mouth or by injection into a vein. It is also available in the fixed-dose combination medication omeprazole/sodium bicarbonate as Zegerid and as Konvomep.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462265
- Drug.image
- Omeprazole enantiomers labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.chirality
- Racemic mixture
- Drug.width
- 350
- Drug.image2
- Omeprazole enantiomers ball-and-stick models from xtal 2015.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 350
- Drug.tradename
- Losec, Prilosec, others
- Drug.MedlinePlus
- a693050
- Drug.DailyMedID
- Omeprazole
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth, intravenous
- Drug.class
- Proton-pump inhibitor
- Drug.ATC_prefix
- A02
- Drug.ATC_suffix
- BC01
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C17H19N3O3S
- Molecular weight
- 345.4 g/mol
- IUPAC name
- 6-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole
- SMILES
- CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
- InChIKey
- SUBDBMMJDZJVOS-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 96.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 345.114712
Show 7 more facts
- Commons category
- Omeprazole
- chemical formula
- C₁₇H₁₉N₃O₃S
- World Health Organisation international non-proprietary name
- 奥美拉唑
- canonical SMILES
- CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
- MCN code
- 2933.39.46
- stylized name
- PriLOSEC
- defined daily dose
- 20
Sources (7)
via Wikidata · CC0
~13 min read
Article
20 sectionsContents
- Medical uses
- Peptic ulcers
- Adverse effects
- Long-term use
- Pregnancy and breastfeeding
- Interactions
- Pharmacology
- Pharmacokinetics
- Bioactivation
- Chirality
- Mechanism of action
- Chemistry
- Measurement in body fluids
- History
- Society and culture
- Economics
- Brand names
- Veterinary uses
- References
- Further reading
Omeprazole, sold under the brand names Prilosec and Losec among others, is a medication used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. Omeprazole is a proton-pump inhibitor (PPI) and its effectiveness is similar to that of other PPIs. It can be taken by mouth or by injection into a vein. It is also available in the fixed-dose combination medication omeprazole/sodium bicarbonate as Zegerid and as Konvomep.
Common side effects include nausea, vomiting, headaches, abdominal pain, and increased intestinal gas. Serious side effects may include Clostridioides difficile colitis, an increased risk of pneumonia, an increased risk of bone fractures, and the potential of masking stomach cancer. Whether it is safe for use in pregnancy is unclear. It works by blocking the release of stomach acid.