Esomeprazole
The S-isomer of omeprazole: a proton pump inhibitor for reflux disease, ulcers, NSAID ulcer prevention and H. pylori eradication.
Drug card
- How it works
- Blocking the stomach's proton pump (H+/K+ ATPase) to stop acid secretion
- Used for
- Gastroesophageal reflux disease and erosive esophagitis
- Preventing NSAID-related stomach ulcers
- H. pylori eradication, with amoxicillin and clarithromycin
- Stomach ulcers
- Known for
- C. difficile diarrhea
- Fractures with long-term use
- Low magnesium with long-term use
- Its name
- -prazole means a proton pump inhibitor
Study it as a flashcard, and it comes back before you forget it.
Mechanism of action
How does esomeprazole work?
The S-isomer of omeprazole, which itself is a mix of S and R forms. In the acid of the parietal cell it is protonated into an achiral sulfenamide that bonds covalently to the H+/K+ ATPase, stopping basal and stimulated acid secretion. Like omeprazole, it inhibits CYP2C19 and reduces the active metabolite of clopidogrel.
Like other proton pump inhibitors: PPIs are prodrugs. They collect in the acidic canaliculi of gastric parietal cells, where acid turns them into an active sulfenamide that binds the H+/K+ ATPase (the proton pump) through covalent disulfide bonds. This shuts off the last step of acid secretion, basal and stimulated alike, and because the bond is irreversible the effect outlasts the drug's short stay in the blood.
Uses
What is esomeprazole used for?
- Gastroesophageal reflux disease and erosive esophagitis
- Preventing NSAID-related stomach ulcers
- H. pylori eradication, with amoxicillin and clarithromycin
- Stomach ulcers
- Zollinger-Ellison syndrome
Side effects
Side effects of esomeprazole
- C. difficile diarrheaKnown forSerious
- Fractures with long-term useKnown forSerious
- Low magnesium with long-term useKnown forSerious
- Headache
- Diarrhea
- Nausea
- Abdominal pain
- Flatulence
- Constipation
- Dry mouth
- Vitamin B12 deficiency after years of use
- Acute interstitial nephritisSerious
Known for marks what an exam expects you to know it for.
Watch for
Cautions and what sets it apart
- Avoid with clopidogrel: esomeprazole lowers its active metabolite and its antiplatelet effect.
- Contraindicated with rilpivirine; avoid with nelfinavir.
- Monitor INR with warfarin and tacrolimus levels; consider pausing it during high-dose methotrexate.
Good to know: As one isomer of omeprazole, it shares omeprazole's side effects and its CYP2C19 interaction with clopidogrel.
Remember it
A way to remember it
CLIMB
- C
- C. difficile diarrhea
- L
- Lupus erythematosus, cutaneous or systemic
- I
- Interstitial nephritis
- M
- Magnesium falls (hypomagnesemia)
- B
- B12 deficiency
Five less common but serious PPI risks to remember, alongside fractures with long-term use.
Written for biofideX
Its name
-prazole means proton pump inhibitor
Omeprazole, esomeprazole, lansoprazole and pantoprazole block the H+/K+ ATPase of parietal cells. Aripiprazole, an antipsychotic, ends in -piprazole, which WHO now discourages.
- Every drug name stem
Its class
Proton pump inhibitors
Other proton pump inhibitors with a card:
Easily mixed up with H2 receptor antagonists.
Sources
Checked against
Written for biofideX in plain words, after checking these references:
- Esomeprazole magnesium delayed-release capsules: label (DailyMed)
- Esomeprazole (NCI Thesaurus)
- About esomeprazole (NHS)
For learning pharmacology, not for treatment decisions: no doses are given, and a prescriber, pharmacist or the product's own label is the word on any one patient. Spotted a mistake? Tell us and we'll correct it.
Stomach and gut
Esomeprazole is one of 15 drugs practiced together here: their classes, how they work, what they treat and what they're known for.
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