Structure via PubChem · Public domain (PubChem)
esomeprazole
Sign in to saveAlso known as (S)-omeprazole, (-)-omeprazole, (S)-(-)-omeprazole, (−)-omeprazole, (S)-(−)-omeprazole, esomeprazol, omeprazole S-form
Esomeprazole, sold under the brand name Nexium (or Neksium) among others, is a medication which reduces stomach acid. It is used to treat gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other proton pump inhibitors (PPIs). It is taken by mouth or injection into a vein.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 477167063
- Drug.image
- Esomeprazole.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 245
- Drug.image2
- Esomeprazole ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250
- Drug.tradename
- Nexium, others
- Drug.MedlinePlus
- a699054
- Drug.DailyMedID
- Esomeprazole
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth, intravenous
- Drug.class
- Proton pump inhibitor
- Drug.ATC_prefix
- A02
- Drug.ATC_suffix
- BC05
- Drug.legal_AU
- S2
via Wikipedia infobox
Chemical data
- Formula
- C17H19N3O3S
- Molecular weight
- 345.4 g/mol
- IUPAC name
- 6-methoxy-2-[(S)-(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole
- SMILES
- CC1=CN=C(C(=C1OC)C)C[S@](=O)C2=NC3=C(N2)C=C(C=C3)OC
- InChIKey
- SUBDBMMJDZJVOS-DEOSSOPVSA-N
- XLogP
- 2.2
- Polar surface area
- 96.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2001
- Admin. routes
- oral, parenteral
- Indications
- Peptic ulcer, gastroesophageal reflux disease, hemorrhage, Nausea
via ChEMBL · EBI
Research
2,409 papers- Esomeprazole.Drugs · 2000
- Comparative effectiveness and tolerability of esomeprazole and omeprazole in gastro-esophageal reflux disease: A systematic review and meta-analysis.International journal of clinical pharmacology and therapeutics · 2015
- Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial.The American journal of gastroenterology · 2001
- Comparison of the effects of esomeprazole 40 mg, rabeprazole 20 mg, lansoprazole 30 mg, and pantoprazole 40 mg on intragastrıc pH in extensive metabolizer patients with gastroesophageal reflux disease.The Turkish journal of gastroenterology : the official journal of Turkish Society of Gastroenterology · 2016
- Esomeprazole: a clinical review.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 2002
via PubMed
Wikidata facts
- Subclass of
- omeprazole
- Has part
- carbon
- Mass
- 345.114712
- Has use
- medication
Show 8 more facts
- chemical formula
- C₁₇H₁₉N₃O₃S
- medical condition treated
- peptic ulcer disease
- isomeric SMILES
- CC1=CN=C(C(=C1OC)C)C[S@](=O)C2=NC3=C(N2)C=C(C=C3)OC
- canonical SMILES
- CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
- World Health Organisation international non-proprietary name
- esomeprazole
- stylized name
- NexIUM
- Commons category
- Esomeprazole
- defined daily dose
- 30
via Wikidata · CC0
~10 min read
Encyclopedic overview
18 sectionsContents
- Medical use
- Gastroesophageal reflux disease
- Duodenal ulcers
- Efficacy
- Adverse effects
- Interactions
- Pharmacokinetics
- Dosage forms
- Multiple-unit pellet system
- Society and culture
- Global distribution
- Economics
- Controversy
- Brand names
- Veterinary use
- Other uses
- References
- Further reading
Esomeprazole, sold under the brand name Nexium (or Neksium) among others, is a medication which reduces stomach acid. It is used to treat gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other proton pump inhibitors (PPIs). It is taken by mouth or injection into a vein.
Common side effects include headache, constipation, dry mouth, and abdominal pain. Serious side effects may include angioedema, Clostridioides difficile infection, and pneumonia. Use in pregnancy appears to be safe, while safety during breastfeeding is unclear. Esomeprazole is the (S)-(−)-enantiomer (or less specifically the S-isomer) of omeprazole. It works by blocking H+/K+-ATPase in the parietal cells of the stomach.
Excerpted from Wikipedia’s “esomeprazole” article, available under the CC BY-SA 4.0 licence.