Talk:Vancomycin/Archive 1

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)

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)

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)

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)

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)

The statement that "Vancomycin must be administered in a dilute solution slowly, over at least 60 minutes" cannot be entirely correct. As part of my recovery from sepsis, after I didn't need to be hospitalized any longer, they had me inject myself with Vancomycin every 4 hours through a PICC for several weeks. The administration took less than a minute, no one ever told me to do it slowly, and no problems resulted. Ornithikos (talk) 22:52, 28 March 2013 (UTC) Well, that just means somebody screwed up by not telling you to go slow, and you happened to get away with it. The rate of various problems with vanco, including ototoxicity and skin reactions, goes up at infusion rates over 10 mg a minute (which you certainly exceeded by a factor of many times!). But it's not an invariable thing, so "must be" is probably too strong. "For best safety, is recommended to be" would be better. SBHarris 01:19, 29 March 2013 (UTC)

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)

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)

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)

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)

Obesity leads to dosage problems across the board (not solely due to weight:drug ratios, but moreso due to fat sequestering), and is not specific to vancomycin. -76.172.41.63 (talk) 13:36, 6 August 2008 (UTC)

That was a pointless study. I'm stupefied why they couldn't correlate their dose findings with at least troughs (or better yet, outcomes). - Emt147 ^Burninate! 08:23, 30 August 2008 (UTC)

Topical Vancomycin?

Topical solutions aren't mentioned in the article at all. Vancomycin is not solely a systemic (intravenous) antibiotic. -76.172.41.63 (talk) 13:36, 6 August 2008 (UTC)

MRSA treatment?

This section contradicts itself:

Vancomycin is indicated for the treatment of serious, life-threatening infections by Gram-positive bacteria which are unresponsive to other less toxic antibiotics. In particular, vancomycin should not be used to treat methicillin-sensitive Staphylococcus aureus because it is inferior to penicillins such as nafcillin.[12][13] The increasing emergence of vancomycin-resistant enterococci has resulted in the development of guidelines for use by the Centers for Disease Control (CDC) Hospital Infection Control Practices Advisory Committee. These guidelines restrict use of vancomycin to the following indications: treatment of serious infections caused by susceptible organisms resistant to penicillins (methicillin-resistant Staphylococcus aureus and multi-resistant Staphylococcus epidermidis (MRSE)) or in individuals with serious allergy to penicillins

Is it used to treat mrsa or not? Anriar (talk) 21:10, 16 September 2008 (UTC)

Er, methicillin-sensitive Staph aureus isn't MRSA. Sounds like it's self-consistent that one should not use vanco if it's methicillin-sensitive (instead using other treatments, for example, methicillin), but only use vanco if treating something resistant to other treatments. DMacks (talk) 21:41, 16 September 2008 (UTC)

TDM

The vancomycin therapeutic drug monitoring is far more confusing than what the article reflects. Despite the absence of hard evidence and objections from some experts in the field, the ACCP/IDSA guidelines on HCAP and the IDSA guidelines on meningitis still recommend minimal trough concentrations and there is data that AUC24/MIC ratios predict response to therapy. Finally, despite the purportedly concentration-independent killing there is an increasing number of case reports of treatment failures with VISA and heterogeneously-susceptible strains (plus the aforementioned AUC24/MIC data). - Emt147 ^Burninate! 21:44, 28 September 2008 (UTC)

Expensive?

I've heard of this costing $2500 for a 5-day dose; if this can be verified and sourced, the article should talk about how expensive it is. 76.180.19.184 (talk) —Preceding undated comment added 10:48, 28 November 2009 (UTC).

I just started taking Vancomycin after other antibiotics did not work. There was a problem of getting my insurance to pay for this medication due to its high cost. This caused a three day delay, while the C-def continued to grow. For a 10 supply it was close to $3,000. It does not make sense to me that a drug that should be generic by now costs this much. Added to the cost was all of the man hours from my doctor's office, Walgreen's, Express Scripts and Anthem Ins. Most important to me is that I have been ill for over two months. July 13, 2013. — Preceding unsigned comment added by 2602:306:3731:4B00:6928:10D7:E938:4A3B (talk) 22:37, 13 July 2013 (UTC)

I had C dif and i was prescriber vancomycin it was 3000 for 10 days of capsules i think its expensive because they have to go in the jungle for this antibiotic A8v (talk) 12:20, 20 August 2015 (UTC)

IV therapy confusion: PICC vs. midline catheter

Excellent article. However, I found the following sentence confusing and misleading: The caustic nature of Vancomycin makes IV therapy using midline PICC lines a risk for thrombophlebitis.[21]

There is no such thing as a midline PICC! By definition, a midline catheter is a peripheral IV 3 to 10 inches long inserted in the arm that doesn't extend past the axilla. A PICC (peripherally inserted central catheter) is just what it says: a central line that terminates in the vena cava that is inserted peripherally, usually in the antecub or upper arm.

The article referenced clearly spells out the differences. It shows the danger of giving vanc via midline (midlines being very rare, in the US anyway) and why this should probably be avoided: deep arm vein where vasculitis/infiltration/thrombo would be hard to assess. I see no reason why administering Vanc via a PICC is any different than administering it via any other central line ... quite probably the safest way to administer IV Vanc in my opinion.

I'm bringing this up because I would hate to have home IV therapy patients reading that disinformation and panicking over their PICC. The sentence would be fine if it read, The caustic nature of Vancomycin makes IV therapy using a midline IV a risk for thrombophlebitis.[21] If you read ref 21 you'll see what I mean.

Thanks. Hajnalka (talk) DL —Preceding undated comment added 22:18, 19 April 2010 (UTC).

I went ahead and changed it: my first wikipedia edit. Hajnalka (talk) 23:27, 9 July 2010 (UTC)

Edit request

The second paragraph of the lede starts with:"The compound was industrially produced by fermentation...". Was? This implies it is now synthesized or produced some other way. Looking at its structure, I find that hard to believe, but if it is true then certainly the way(s) it is CURRENTLY made is what should appear in the lede. I suggest either replacing the "was" with the present tense or describing its current manufacture/syntheses.Abitslow (talk) 22:11, 17 March 2015 (UTC)