Prilosec (omeprazole) and Nexium (esomeprazole)

Esomeprazole
Also known as: Nexium, Omeprazole magnesium, Esomeprazole magnesium, 161973-10-0, H 168/68
magnesium, S1743_Selleck, Prilosec OTC (TN), AC1NSJYQ, AC1L2XM7
Molecular Formula: C
34
H
36
MgN
6
O
6
S
2
Molecular Weight: 713.12124 InChIKey:
KWORUUGOSLYAGD-UHFFFAOYSA-N
The S-isomer of omeprazole. From: MeSH

Descriptors
IUPAC Name: magnesium;5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-
yl)methylsulfinyl]benzimidazol-1-ide
InChI: InChI=1S/2C17H18N3O3S.Mg/c2*1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-
3)7-14(13)20-17;/h2*5-8H,9H2,1-4H3;/q2*-1;+2
InChIKey: KWORUUGOSLYAGD-UHFFFAOYSA-N
Canonical SMILES : CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C([N-
]2)C=CC(=C3)OC.CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C([N-]2)C=CC(=C3)OC.[Mg+2]

LATAR BELAKANG
Nexium has been approved by the FDA for the relief of heartburn and other symptoms associated
with gastroesophageal reflux disease (GERD) and for the healing of erosive esophagitis, a potentially
serious condition associated with GERD. The FDA also approved Nexium for maintenance of healing
of erosive esophagitis and, in combination with amoxicillin and clarithromycin, for the eradication of
Helicobacter pylori infection in patients with duodenal ulcer disease.
Nexium is derived from Prilosec (omeprazole). Prilosec contains a racemic mixture of the D- and L-
forms (isomers) of omeprazole. Nexium contains only one of the isomers. Both Prilosec and Nexium
are known as proton pump inhibitors.
As many as 25 million adults experience heartburn on a daily basis. Although heartburn is the most
common symptom of GERD, the condition is also often marked by other symptoms - such as a sour
taste in the mouth or difficulty swallowing - related to the backing up of harsh stomach acid into the
esophagus. When this acid reflux damages the lining of the esophagus, it may lead to a potentially
more serious condition called erosive esophagitis that can lead to narrowing or ulceration of the
esophagus.
Nexium telah disetujui oleh FDA untuk menghilangkan heartburn dan gejala lain yang berhubungan
dengan penyakit gastroesophageal reflux ( GERD ) dan untuk penyembuhan esofagitis erosif , suatu
kondisi yang berpotensi serius yang berhubungan dengan GERD. FDA juga menyetujui Nexium untuk
pemeliharaan penyembuhan esofagitis erosif dan, dalam kombinasi dengan amoksisilin dan
klaritromisin , untuk pemberantasan infeksi Helicobacter pylori pada pasien dengan penyakit ulkus
duodenum .
Nexium berasal dari Prilosec ( omeprazole ) . Prilosec berisi campuran rasemat dari D - dan L - bentuk
( isomer ) omeprazole . Nexium hanya berisi satu dari isomer . Kedua Prilosec dan Nexium dikenal
sebagai inhibitor pompa proton .
Sebanyak 25 juta orang dewasa mengalami heartburn setiap hari . Meskipun heartburn adalah gejala
yang paling umum dari GERD , kondisi ini juga sering ditandai dengan gejala lain - seperti rasa asam
di mulut atau kesulitan menelan - terkait dengan back up dari asam lambung yang keras ke
kerongkongan. Ketika refluks asam ini merusak lapisan kerongkongan , itu dapat menyebabkan
kondisi yang berpotensi lebih serius yang disebut esofagitis erosif yang dapat menyebabkan
penyempitan atau ulserasi esofagus .
Target Interactions
Target : Potassium-transporting ATPase alpha chain 1
Action : inhibitor
General Function : Inorganic ion transport and metabolism
Specific Function : Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+)
ions across the plasma membrane. Responsible for acid production in the stomach
Gene Name : ATP4A
GenBank Gene : J05451
GenBank Protein : 561634
References :
Saccar CL: The pharmacology of esomeprazole and its role in gastric acid related diseases.
Expert Opin Drug Metab Toxicol. 2009 Sep;5(9):1113-24. PubMed: 19606942
McKeage K, Blick SK, Croxtall JD, Lyseng-Williamson KA, Keating GM: Esomeprazole: a review
of its use in the management of gastric acid-related diseases in adults. Drugs.
2008;68(11):1571-607. PubMed: 18627213
Vachhani R, Olds G, Velanovich V: Esomeprazole: a proton pump inhibitor. Expert Rev
Gastroenterol Hepatol. 2009 Feb;3(1):15-27. PubMed: 19210109
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan
1;30(1):412-5. PubMed: 11752352
Interactions
Enzyme : Cytochrome P450 2C19
Action :
substrate
inhibitor
General Function : Secondary metabolites biosynthesis, transport and catabolism
Specific Function : Responsible for the metabolism of a number of therapeutic agents such as
the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam,
propranolol, citalopram and imipramine
Gene Name : CYP2C19
GenBank Gene : M61854
GenBank Protein : 181344
References :
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R,
Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450
enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010
Jan;38(Database issue):D237-43. Epub 2009 Nov 24. PubMed: 19934256
AstraZeneca. Nexium (esomeprazole magnesium) delayed-release capsules and packets
for delayed-release oral suspension prescribing information. Wilmington, DE; 2008 Dec.
Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a
review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302. PubMed:
16961157
from DrugBank
Interactions
Enzyme : Cytochrome P450 3A4
Action : substrate
General Function : Involved in monooxygenase activity
Specific Function : Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver
microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It
performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation,
midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds,
including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
Gene Name : CYP3A4
GenBank Gene : M18907
References : AstraZeneca. Nexium (esomeprazole magnesium) delayed-release capsules and
packets for delayed-release oral suspension prescribing information. Wilmington, DE; 2008 Dec.

INDICATIONS AND USAGE
NEXIUM is a proton pump inhibitor indicated for the following: (1)
Treatment of gastroesophageal reflux disease (GERD) (1.1) (1)
Risk reduction of NSAID-associated gastric ulcer (1.2) (1)
H. pylori eradication to reduce the risk of duodenal ulcer recurrence (1.3) (1)
Pathological hypersecretory conditions including Zollinger-Ellison syndrome (1.4) (1)

Mechanism of Action
Esomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific
inhibition of H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton
pump, esomeprazole blocks the final step in acid production, thus reducing gastric acidity.
This effect is dose-related up to a daily dose of 20 to 40 mg and leads to inhibition of gastric
acid secretion. (Nexium Prescribing Information)

Side Effects
Side effects reported with Nexium use include (but are not limited to) the following:
Headache
Diarrhea
Abdominal pain
ADVERSE REACTIONS
Most common adverse reactions: (6)
Adult (> 18 years) use (incidence > 1%): (6)
Headache, diarrhea, nausea, flatulence, abdominal pain, constipation, and dry mouth (6.1)
(6)
Pediatric (1 - 17 years) use (incidence > 12%): (6)
Headache, diarrhea, abdominal pain, nausea, and somnolence (6.1) (6)
Sintesis