Talk:Vancomycin

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[edit] Early comments

Could we have some information about who manufactures it and when its patent will run out?

Its patent was held by Eli Lilly but it has now run out and vancomycin is available as a generic drug. -- Someone else 22:09 Nov 13, 2002 (UTC)

Also, I don't understand the paragraph about oral vancomycin. It is not absorbed by the bowel, but why does that help in treating the antibiotic overdose? AxelBoldt 17:05 Nov 13, 2002 (UTC)

The initial use of broad-spectrum antibiotics results in overgrowth within the bowel of Clostridium difficile. This bacterium produces toxin that cause the condition "pseudomembranous enterocolitis". It's very frequently seen after the use of clindamycin, cephalosporins and (less often) penicillin, because these antibiotics kill the normal bowel flora that generally keeps the C. difficile under control. The vancomycin, with its high concentration within the bowel, is used to kill the C. difficile: the previous antibiotics usually have already been discontinued, so what's being treated is not so much a case of antibiotic overdose as an infection caused by indiscriminate or profligate antibiotic overuse. -- Someone else 22:09 Nov 13, 2002 (UTC)


Thanks a lot, that clarifies it; I'll add it to the article. AxelBoldt 03:51 Nov 14, 2002 (UTC)

[edit] Structure

EDITED NOTE - the structure to the right shows the stererochemistry of the C6 carbon atom as S. I believe that it should in fact be R. The C-6 carbon atom is on the RHS & carries the leucine group (-NH-CO-CH(NHMe)-CH2CH(CH3). You can check the structure at www.chemfinder.com - type "vancomycin" into the search engine. -- 195.157.146.246

Thanks for the detail in your explanation. The stereochemistry I've drawn here is based on that in Foye's Medicinal Chemistry1, and seems consistent with that in the Vancocin CP Approved Product Information2. However, my understanding is that vancomycin is actually a blend of several molecules1; so it may well be that both the Chemfinder and this one are valid. Probably need another opinion from a medicinal chemist...
1. Mitscher LA (2002). Antibiotics and Antimicrobial Agents. In Williams DA & Lemke TL (Eds.), Foye's Principles of Medicinal Chemistry (5 ed.). Philadelphia: Lippincott Williams & Wilkins.
2. Eli Lilly Australia Pty Ltd (2002). Vancocin CP Approved Product Information. West Ryde: Eli Lilly Australia
Techelf 07:09, 16 Nov 2004 (UTC)
There appears to be a significant number of discrepancies with the vancomycin structure as presented in a number of sources. The structure shown here is likely incorrect simply due to the discrepancy with the molecular formula ( as drawn, appears to be: C66 H78 Cl N9 O21 ). If the NIH structure can be trusted it appears the graphic is missing 3 oxygens and a chlorine, minimally, cf,
NIH structure
FDA MedWatch
McGill
-TechChem 19:26, 8 February 2006 (UTC)
Hi TechChem, thanks for pointing out the problems with my original vancomycin structure. I've redrawn Vancomycin.png, basing it on the structure from the Vancocin PI, and retained the previous style that I used for clarity. Cheers. -Techelf 10:43, 10 February 2006 (UTC)
The structure of vancomycin is still slightly incorrect (both the NIH and FDA structures are incorrect as well, the McGill link is broken). The current structure lacks stereochemistry in the glycoside portion of the molecule. In addition, the atropisomer stereochemistry of residue 6 (upper left macrocycle) is incorrect. The chlorine atom should be attached inside the macrocycle (still ortho to the diaryl ether linkage). Also, the amide linkage between residues 5 and 6 should be cis, not trans as depicted. The structure also lacks depiction of the atropisomer stereochemistry in each of the macrocyclic rings (see Boger. Scroll down to find the structure of the aglycon). The crystal structure of vancomycin can be found at the Protein Data Bank. Enter "vancomycin" into the search engine at the top of the page. Vancomycin is only one molecule, not a blend. It is typically sold as the HCl salt. -Part time medchemist--24.215.246.53 18:11, 8 July 2006 (UTC)
Thanks mate, I wasn't aware of the significance of atropisomerism. I hope the updated structure is correct. -Techelf 11:36, 9 July 2006 (UTC)

[edit] Cancer caused by Vancomycin

I am looking for information about cancer caused by this drug when taken oraly.

The Approved Product Information in Australia and Data Sheet in New Zealand both state something to the effect of, "Although no long-term studies in animals have been performed to evaluate carcinogenic potential, no mutagenic potential of vancomycin was found in standard laboratory tests." (from Vancocin pulvule datasheet) Put into perspective, though, vancomycin is the drug of last resort and any hypothetical risk of carcinogenesis is probably far outweighed by the potentially-fatal effects of staphylococcal enterocolitis or C. difficile pseudomembranous colitis. -Techelf 10:20, 4 May 2005 (UTC)

[edit] Oral bioavailability contradition?

In infobox states:

Bioavailability: negligible (oral)
Routes: IV, oral

Is that "negligible" oral bioavailability sufficient to make that a viable route of administration? DMacks 15:31, 8 June 2006 (UTC)

This isn't a contradiction, just a slightly confusing issue. Bioavailability refers to the amount of drug that is absorbed into the bloodstream, and the bioavailability of oral vancomycin is indeed negligible -- it cannot be used orally to treat a systemic infection, which is usually an inconvenience. However, there is one special case when this property is advantageous, which is when the infection is contained within the intestines. In this case, the drug can very effectively treat the infection when given orally, without any of the adverse effects that might be caused with systemic absorption.
I hope that makes sense...if you want to clarify the part of the article you found confusing, I'll be happy to take a look and make sure what you say is correct.  — JVinocur (talk • contribs) 23:41, 21 June 2006 (UTC)
Ah, that makes quite good sense actually, and is indeed mentioned in the article—no change needed in the wording. I guess I always interpretted "oral" to lead to systemic absorption, not "topical for inner surface of GI tract":) DMacks 19:26, 27 June 2006 (UTC)
Glad to help...y'know, "topical for the GI tract" is an excellent turn of phrase. I'll have to remember that one.  — JVinocur (talk • contribs) 21:48, 27 June 2006 (UTC)

[edit] Red man syndrome

I see that someone just requested an article on Red man syndrome (the vancomycin infusion reaction). It's covered very briefly in this article (see Vancomycin#Dosing), and I'm undecided on whether it needs a separate article. It's a reaction that occurs only with this medication, so I'm not sure there's much benefit for separating it out; I just made it redirect here. But just in case anyone wants to really improve that section and/or make a separate article, there's an excellent online summary at [1].  — JVinocur (talk • contribs) 23:41, 21 June 2006 (UTC)

It's I who put in that request, and I didn't realize that red man's occurs only with vanc. As a vanc patient warned about fast infusion because of red man's, I decided to look for it on WP; not finding it (and with WP's own search engine not finding this article for some reason), I put in a request for it. But that doesn't mean I would object a redir instead: not at all.—msh210℠ 01:12, 22 June 2006 (UTC)
Recently, I was in the hospital to have pectus excavatum repaired. The repair became infected by MRSA and I was on IV vancomycin to combat the infection. My allergic reaction became severe and I learned it was called red man syndrome. While I don't think it deserves a separate article, I do think more information should be provided about it. –Wlmaltby3 02:30, 10 July 2006 (UTC)
Well okay, go ahead and add some! I think you'll find the link I provided above to be an excellent reference...  — JVinocur (talk • contribs) 03:47, 10 July 2006 (UTC)
The current result is that there is a link but it just redirects to the same page. that is silly. 71.196.231.154 (talk) 22:06, 15 January 2008 (UTC)

[edit] Avoparcin - missing article

Hello,

There's an excellent article about Avoparcin on Australian Pesticides and Veterinary Medicines Authority website [[2]]. It's a good complement to the resistant section. Someone could create this article (I'm not an english native-speaker, so I can't help).

HTH,

RFreire1978 21:56, 4 March 2007 (UTC)

[edit] Stain Name

The strain is was down as Steptomyces(sp?) but I've changed it to Amycolatopsis Orientalis, for two reasons. 1) it ages with later in the article, 2) it's what the elily lilly strain in our lab has the label on which I believe is the same strain, but no need to take my word for it. —Preceding unsigned comment added by 131.111.8.102 (talk) 15:27, 12 December 2007 (UTC)

[edit] Strain Name

This still needs clarification - it is referred to by two different (but very similar - possibly someone was confused) names, one of which has a wiki article. Reb42 (talk) 20:11, 25 March 2008 (UTC)

[edit] Obesity

Study shows that obesity leads to routine underdosing of vancomycin: doi:10.1016/j.amjmed.2008.01.046 JFW | T@lk 11:14, 21 May 2008 (UTC)