Esomeprazole

Esomeprazole
Clinical data


Pronunciation	/ˌɛsoʊˈmɛprəˌzoʊl, -ˈmiː-, -ˌzɒl/
Trade names	Nexium, many others
AHFS/Drugs.com	Monograph
MedlinePlus	a699054
License data	US FDA: Esomeprazole
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral, IV
ATC code	A02BC05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: General sales list (GSL, OTC) US: Rx only IV OTC oral
Pharmacokinetic data
Bioavailability	50 to 90%
Metabolism	Hepatic (CYP2C19, CYP3A4)
Biological half-life	1–1.5 hours
Excretion	80% Renal 20% Faecal
Identifiers
IUPAC name (S)-(−)-5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3H-benzoimidazole
CAS Number	119141-88-7^N
PubChem (CID)	9579578
DrugBank	DB00736^Y
ChemSpider	7843323^N
UNII	N3PA6559FT^Y
KEGG	D07917^Y
ChEBI	CHEBI:50275^Y
ChEMBL	CHEMBL1201320^N
ECHA InfoCard	100.149.303
Chemical and physical data
Formula	C₁₇H₁₉N₃O₃S
Molar mass	345.417 g/mol
3D model (Jmol)	Interactive image
SMILES COc1ccc2nc([nH]c2c1)S(=O)Cc1ncc(C)c(OC)c1C
InChI InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m1/s1^Y Key:SUBDBMMJDZJVOS-XMMPIXPASA-N^Y
^NY (what is this?)

Esomeprazole sold under the brand name Nexium (or Nexum) among others, is a proton-pump inhibitor which reduces stomach acid. It is used in the treatment of dyspepsia, peptic ulcer disease, gastroesophageal reflux disease, and Zollinger-Ellison syndrome.

It decreases secretion of acid through inhibition of the H⁺/K⁺-ATPase in the parietal cells of the stomach. By inhibiting the functioning of this transporter, the drug prevents formation of stomach acid.

Esomeprazole is the (S)-(−)-enantiomer of omeprazole. Esomeprazole is currently sold over the counter in the US, the UK and Australia.

The primary uses of esomeprazole are gastroesophageal reflux disease, treatment and maintenance of erosive esophagitis, treatment of duodenal ulcers caused by H. pylori, prevention of gastric ulcers in those on chronic NSAID therapy, and treatment of gastrointestinal ulcers associated with Crohn's disease.

Gastroesophageal reflux disease (GERD) is a condition in which the digestive acid in the stomach comes in contact with the esophagus. The irritation caused by this disorder is known as heartburn. Long-term contact between gastric acids and the esophagus can cause permanent damage to the esophagus. Esomeprazole reduces the production of digestive acids, thus minimizing their effect on the esophagus.

Esomeprazole is combined with the antibiotics clarithromycin and amoxicillin (or metronidazole instead of amoxicillin in penicillin-hypersensitive patients) in a 10-day eradication triple therapy for Helicobacter pylori. Infection by H. pylori is a causative factor in the majority of peptic and duodenal ulcers.

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Wikipedia