Talk:Esomeprazole

What

What I have drawn is, actually, the correct structure of S-omeprazole. The S designation of this molecule is with respect to its structure in vivo - where the sulfinyl moiety is ionised, and there is an additional hydrogen substituent off the chiral sulfur. Under these circumstances the stereochemistry is clearly S. So whilst, technically, this drawing may be R, it actually does represent the structure of S-omeprazole.Techelf 11:14, 21 Oct 2004 (UTC)

I do not agree. Omeprazole is the compound we have in the Nexium bottle. The formula here represents R-omaprazole, therefore it should be fixed. You might make a mistake when redrawing the formula, you pribably did functional group/molecule rotations and have forgotten to follow this motion and change the stereo bond type. Try to imagine the molecule in 3D-space :). If I'm wrong (I'm almost sure I'm not) please give me some reasonable explanation. Regards, Mykhal 14:33, 22 Oct 2004 (UTC)

I concede the point and have revised the drawing accordingly. I had initially (wrongly) supposed that the orientation of the substituents off the chiral sulfur was of a trigonal planar configuration; therefore I had assumed that the orientation of the oxygen substituent would not make a difference. In retrospect, I've realised that the sulfur substituents have a tetrahedral configuration; so you are right about the oxygen substituent being inverted - well spotted. Techelf 06:46, 23 Oct 2004 (UTC)

Thank you. I know, this is not obvious, that on the sulfur atom is lone electron pair which is the fourth "substituent" with lowest priority.. Mykhal 08:49, 23 Oct 2004 (UTC)

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The following information from the DrugBank should be incorporated (not copied!) into this article:
"Esomeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Esomeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase enzyme system at the secretory surface of the gastric parietal cell. Because this enzyme system is regarded as the acid (proton) pump within the gastric mucosa, Esomeprazole has been characterized as a gastric acid-pump inhibitor, in that it blocks the final step of acid production. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus." [1]

I'll probably do it myself eventually, if no one else does. Fuzzform 02:13, 22 February 2006 (UTC)

Should be in the PPI article, not here. --Elvey (talk) 09:26, 4 June 2012 (UTC)

Reverting edits

With all of the citations that I provided -- please provide a rationale as to why you keep reverting text which enhances this information? —Preceding unsigned comment added by Chrisgaffneymd (talk • contribs)

I have replied on your talk page. Fvasconcellos 00:35, 28 October 2006 (UTC)

Interaction with other drugs, e.g. SSRIs?

I have noticed that Esomeprazole shares metabolic mechanisms with other drugs such as Clonazepam, and SSRIs like Escitalopram and Citalopram. Can someone look up if there is expected to be heightened serum levels of these drugs while on Esomeprazole due to their shared hepatic clearance mechanisms? If so, I think this should be included in this article. Please include with a source. --1000Faces (talk) 16:16, 1 December 2009 (UTC)

Done. Fvasconcellos (t·c) 18:49, 1 December 2009 (UTC)

Dosage equivalency with omeprazole?

Is there any literature which cites the dosage equivalency of omeprazole to Esomeprazole? For example, if someone were to switch from 40mg of Esomeprazole, should they switch to 10, 20, 40, or 80mg of omeprazole? If there is data in the literature on this, I think it should be mentioned here. It is touched upon during the Controversy segment, but lacks conclusive statements. --1000Faces (talk) 04:25, 2 December 2009 (UTC)

They're more or less the same thing biochemically, so they're equipotent; the main difference between them is price and patent protection; see the NBC correspondent's comment quoted below. --Elvey (talk) 09:26, 4 June 2012 (UTC)

Poor metabolizers?

The Prilosec article states that: "In theory, by using pure esomeprazole the effect on the proton pump will be equal in all patients, eliminating the poor metabolizer effect." Can this be explained here with citations? It has been mentioned in this article that overcoming individual differences was a reason for developing this drug, but is this what is meant? More clarity is needed. --1000Faces (talk) 15:20, 24 December 2009 (UTC)

There is a 2005 study directly comparing esomeprazole 40mg and osemprazole 20mg as part of triple therapy for H. pylori eradication. The authors' main conclusion was as follows -

"Esomeprazole 40 mg twice daily for triple therapy may improve the H. pylori eradication compared to omeprazole-based therapy, but only for homologous extensive metabolizers of CYP2C19."

The paper is Sheu et al. 2005 Aliment Pharmacol Ther v21, pp.283-88 (doi: 10.1111/j.1365-2036.2005.02281.x), but it is probably behind a paywall. Bonza9683 23:41, 22 October 2012 (UTC) — Preceding unsigned comment added by Bonza9683 (talk • contribs)

80mg comparison

However, a more proper comparison would be with an 80 mg dose of omeprazole because this would contain approximately the same amount of the active enantiomer. However, there are also indications, as shown above, that for omeprazole, both the (R) and (S) enantiomers have the same therapeutic effect. In that case the comparison is valid after all.

If someone can find a source that points this out, it would be useful to have in the article. As it stands now however it's not cited. hbdragon88 (talk) 01:37, 5 January 2010 (UTC)

The Chemicals Structural Diagram is incorrect.

Hey All,

Sorry I am in a rush and am unwell so cannot make the amendment myself but the structural diagram for Esomeprazole is clearly wrong. The fact that the molecule has 3 oxygen atoms but only two are present in the figure is a stark example of just one of the couple of mistakes I witnessed. If someone with more knowledge and experience than myself could please rectify the issue that would be great.

Thanks, Cyn — Preceding unsigned comment added by Cynicle (talk • contribs) 10:34, 12 May 2012 (UTC)

This was exactly the incorrect structure that motivated me to register as a Wiki contributor :) I fixed this while I was on holiday in Italy. At the time I didn't even realise articles had talk pages like this to identify such issues. I'm pretty busy with research so I don't have time to contribute much, but I enjoy adding stubs (with structure and basic cited details) for medicinal molecules that might be generally interesting to the community.

BaeyerDrewson (talk) 01:05, 19 October 2012 (UTC)

UNDUE

This article seems largely duplicative of the PPI article. The bulk of the redundant info should be removed. There also seems to be little mention of the mainstream view of Nexium (Nexium = Prilosec + deceptive marketing), as exemplified by the comments of Robert Bazell, NBC's chief science and health correspondent:

Almost all drugs exist in an equal combination of two mirror images of the same molecule called isomers. Nexium is nothing more than one of the two mirror images that make up Prilosec. AstraZeneca carried out clinical trials comparing Prilosec and Nexium. The most charitable interpretation of the results is that at equal doses Nexium is 3 percent better at relieving symptoms.

The results were so weak that the FDA case officer assigned to review the data concluded that AstraZeneca’s contention that Nexium represented a “significant clinical advance” over Prilosec was “not supported by data.” The top management of the FDA approved Nexium anyway in 2001.

Prilosec now costs about $30 a month. Nexium costs about $200.

If anyone doubts the influence of drug company ads on patients and physicians — consider all those wasted billions of dollars for a pill that sells for more than six times as much as another drug that does the same thing, made by the same company.

Source: http://www.msnbc.msn.com/id/20249591/ns/health-second_opinion/t/costly-side-effects-nexiums-ad-blitz/

Ref. 16 (News Medical)

The website this citation links to appears to use material from the Wikipedia article (it acknowledges this). Isn't this circular referencing? What is the original data from www.news-medical.net that is incorporated into the Wiki page? Bonza9683 16:57, 18 October 2012 (UTC)

largely redundant Intro

The Intro part reads to a large part like an advertisement of the two producing companies, let's put the relevant stuff here, let's have the pharma industry make their own ads and pay for them, okay? If nobody disagrees until the next week, I'll just do the edit in the intro...--Triple5 (talk) 09:46, 18 February 2013 (UTC)