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Former good articleHeparin was one of the Natural sciences good articles, but it has been removed from the list. There are suggestions below for improving the article to meet the good article criteria. Once these issues have been addressed, the article can be renominated. Editors may also seek a reassessment of the decision if they believe there was a mistake.
Article milestones
DateProcessResult
October 16, 2006Good article nomineeListed
March 9, 2010Good article reassessmentDelisted
Current status: Delisted good article

clarification

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Can someone explain to me (i.e. incorporate into the article) why Heparin gel (topical) is sometimes used to treat sports injuries--like sprains, strains, bruises, etc? I can't find anything explaining this, but I have heard people say that it is useful, and here in Germany you can buy "Heparin sport-Gel" from Ratiopharm. Obviously some people think Herparin is effective for things other than blood clots, but I can't find information about this online. I just thought this would be a good addition to the "Other uses" section. 24. February 2006

Considering what the article says, I'd say that the heparin contained in the gel either diffuse through the skin to the injury site, and block the inflammatory response by binding to the inflamatory response enhancer that histamine is. Nikoo

Meat

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reference to slaughtered meat animals is redundant —Preceding unsigned comment added by 72.248.115.194 (talk) 14:58, 20 February 2009 (UTC)[reply]

Delete trade names

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I've never heard of heparin referred to by its trade name. Perhaps delete the brand names? Andrew73 19:33, 22 September 2005 (UTC).[reply]

I deleted the brand names...they seem to clutter the article! Andrew73 16:19, 30 October 2005 (UTC)[reply]
This was probably a bad idea, trade names are always important when identifying drugs. —Preceding unsigned comment added by Mrdeath5493 (talk • contribs) 06:58, 9 September 2009 (UTC)[reply]

Image

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On PubChem[1] an image is available but it's not clear where the repeat moieties connect to. Perhaps a chemist may be able to help. JFW | T@lk 20:55, 28 December 2005 (UTC)[reply]

Fraxiparin

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Please elaborate on fraxiparin, another medicine with function similar to heparin. Thanks borgx (talk) 04:13, 20 February 2006 (UTC)[reply]

Fraxiparin is one of the low molecular weight heparins. Andrew73 02:55, 23 February 2006 (UTC)[reply]

Heparin's inhibiton of PCR?

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What is the mechanism of heparin's purported inhibition of PCR? Is the molecule specific for Taq? For DNA? Does it non-specifically muck things up due to steric hindrance? Does anyone actually reject specimens received in heparin? If not, what is the amplification failure rate for heparinized specimens? Thanks

This may be due to a biochemical property of the compound, that isn't described here : the fact that heparin has typical chemical properties of a nucleic acid backbone analog (glucose instead of ribose, and sulfate instead of phosphate). Heparin is therefore routinely used as a non-specific competitor in RNA/DNA protein binding experiments such as EMSA, since proteins can recognize nucleic acids through specific interactions with the bases, and non-specific, but sometimes important, interactions with the sugar-phosphate backbone.You're welcome ;-) Nikoo

Structure

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I'm don't think the IUPAC name matches the disacchride structure I put up or that the IUPAC name here is very helpful. Take the first line of the IUPAC name below 6- [5- acetylamino- 4,6- dihydroxy-2- I can't work out where the 6- comes from or were the acetylamino group is. Maybe whoever put up the IUPAC name would like to comment? Maybe IUPAC names should only be given when a monosacchride is being described. Then for large polymers such as heparin replace the IUPAC name with a description of the monomers that are joined together, referencing the monosacchrides articles. This would de-clutter things considerably.

Structure part 2

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I got sick of looking at that great long WRONG IUPAC name. I know it came from the pubchem reference 772 but its wrong there as well and so is part of their description in the MeSH section. PubChem got the structure from BioCyc and they've now changed their structure and description in the database but it'll take a few months to show up on line. PubChem have been ignoring me but maybe when BioCyc changes PubChem will as well! Does anyone out there want the IUPAC name back?

The biocyc change now shows up on line, see here, still no luck on changing the pubchem entry.

heparin

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can someone help to undarstand if heparin is oxidable by TOC analysis or if there's a chem method to detect heparin at a low conc.? Partial heparin oxidation, is used in the manufacture of parnaparin and ardeparin (see low molecular weight heparin). Maybe a "complete" oxidation would allow a TOC analysis. How low is a low conc? and is your sample a pure heparin sample or does it contain other material e.g. proteins. We should discuss this on my talk page

GA review

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Excellent figures and clear text. However, more references would be an improvement, particularly in the medical sections. TimVickers 16:10, 16 October 2006 (UTC)[reply]

History

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I believe you are wrong saying that scientist were looking for an anticoagulant. Jay McLean, a PhD under Howell, found what he thought was a phospholipid based on the way he had isolated it [1]. Originally he had called this substance cephalin [2]. He actually was looking for a procoagulant in the (dog) liver, but when he had done experiments he found that an extract of dog liver prolonged the time required for plasma to clot ex vivo [3]. Apart from this, your article aided me a lot for my essay on heparin, thanks for that. Tristan Groot 15:51, 24 Octobre 2006 (The Netherlands)


[1]: Petitou, M., Boeckel, C.A.A. van, Chemical Synthesis of Heparin Fragments and Analogues, Progress in the Chemistry of Organic Natural Products, 60, pp.143 (1992).
[2]: McLean, J., The Thromboplastic Action of Cephalin, American Journal of Physiology, 41, pp.250 (1916).
[3]: Hirsh, J., Heparin, New English Journal of Medicine, 324(22), pp.1565 (1991) in Arbit, E., Oral heparin, status review, Thormbosis Journal, 4, pp.6 (2006).

Highest Negative Charge Density

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Heparin has the highest negative charge density of any known biological molecule. This helps it in its very strong electrostatic interaction with thrombin (in association with antithrombin). (Lehninger Principles of Biochemistry, 4th Ed.). Thought it would be worth mentioning in the article.TwoOars 01:01, 14 March 2007 (UTC)[reply]

Toxic heparin

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I'm confused about the latest edit. My references say heparin entered clinical trials in 1935, but the latest edit tell us that heparin preparations were toxic until 1937 when connaught started producing non-toxic heparin preparations. What was being used in the clincal trials in 1935 and 1936, toxic heparin !!! K.murphy 11:13, 27 March 2007 (UTC)[reply]

I've changed the history to make it clear toxic heparin wasn't being used in clinical trials!! K.murphy 19:37, 21 May 2007 (UTC)[reply]

Acid-based properties

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And what about acid-based properties of heparin? —Preceding unsigned comment added by 82.179.135.20 (talk) 06:34, 8 November 2007 (UTC)[reply]

Like what? K.murphy 22:24, 12 November 2007 (UTC)[reply]

heparin managment

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we want ask if possible to gavin heparin as therapeuti dose (like MI)after 2hour from major surgical like gall bladder remove

breaks down pre-exisintg clots?

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As it stands, the article states: ...heparin does not break down clots that have already formed (unlike tissue plasminogen activator), it allows the body's natural clot lysis mechanisms to work normally to break down clots that have already formed...

Medical uses

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Theres a section mentioning the uses of heparin in combating DVT and Pulmonary emboli, however it also says "but there is no evidence that they are effective at preventing death," but I have to ask, death from what? It's an obsurdly vague cited statement that really only confirms that Heparin, like every other medication ever, doesn't make you immortal.170.173.0.16 (talk) 20:07, 27 February 2009 (UTC)[reply]

I fixed this statement. It cited an article which I read that compared LMWH to Heparin and found no difference in mortality. It did NOT show no evidence of benefit from Heparin. You would be hard pressed to find a recent study that compared Heparin to Placebo since such a study would be turned down by any ethics committee. I also deleted some line about a Scottish recommendation for DVT prevention being aspirin. There has been study in this area and aspirin is actually a poor choice for DVT prevention.Mrdeath5493 (talk) 07:05, 9 September 2009 (UTC)[reply]

Unrealistic protonation state

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Just a quick note that the pKa of those sulfate groups is so low that they would never be protonated in water, as shown in the lewis structure on the main page. Maybe in an organic solvent you could get them as drawn, but not in water. I'd fix it, but my license for chemdraw just ran out. —Preceding unsigned comment added by 128.104.119.87 (talk) 20:09, 30 March 2009 (UTC)[reply]

Green top tubes?

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I work in the Pathology labs of the Midlands NHS and can safely say that all our Lithium Hep. tubes are bright orange, not green topped (those are citrate tubes). Seems a little silly to have a colour top in the article when all companys probably use different colours for their tubes. —Preceding unsigned comment added by 146.227.1.14 (talk) 07:29, 18 January 2011 (UTC)[reply]

Use in cold sore medication

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There is no information regarding the use sodium heparin in topical cold sore medication (ex. lipactin). Gibby is gibby (talk) 16:42, 20 May 2011 (UTC)[reply]

GA Reassessment

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This discussion is transcluded from Talk:Heparin/GA1. The edit link for this section can be used to add comments to the reassessment.

Starting GA reassessment as part of the GA Sweeps process. Jezhotwells (talk) 19:38, 27 February 2010 (UTC)[reply]

Checking against GA criteria

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To uphold the quality of Wikipedia:Good articles, all articles listed as Good articles are being reviewed against the GA criteria as part of the GA project quality task force. While all the hard work that has gone into this article is appreciated, unfortunately, as of March 9, 2010, this article fails to satisfy the criteria, as detailed below. For that reason, the article has been delisted from WP:GA. However, if improvements are made bringing the article up to standards, the article may be nominated at WP:GAN. If you feel this decision has been made in error, you may seek remediation at WP:GAR.

GA review (see here for criteria)
  1. It is reasonably well written.
    a (prose): b (MoS):
    The article appears to contain copyright violations such as:
    The most common disaccharide unit is composed of a 2-O-sulfated iduronic acid and 6-O-sulfated, N-sulfated glucosamine, IdoA(2S)-GlcNS(6S) from {http://www.medic8.com/medicines/Panheprin.html}
    Under physiological conditions, the ester and amide sulfate groups are deprotonated and attract positively-charged counterions to form a heparin salt. from {http://www.medic8.com/medicines/Panheprin.html}
    The three-dimensional structure of heparin is complicated by the fact that iduronic acid may be present in either of two low-energy conformations when internally positioned within an oligosaccharide from {http://www.medic8.com/medicines/Calciparine.html}
    Heparin is a naturally-occurring anticoagulant produced by basophils and mast cells.[10] Heparin acts as an anticoagulant, preventing the formation of clots and extension of existing clots within the blood. from {http://www.medic8.com/medicines/Panheprin.html}
    Danaparoid, a mixture of heparan sulfate, dermatan sulfate, and chondroitin sulfate, can be used as an anticoagulant in patients that have developed HIT. Because danaparoid does not contain heparin or heparin fragments, cross-reactivity of danaparoid with heparin-induced antibodies is reported as less than 10% from {http://www.medic8.com/medicines/Panheprin.html}
    A serious side-effect of heparin is heparin-induced thrombocytopenia (HIT). HIT is caused by an immunological reaction that makes platelets a target of immunological response, resulting in the degradation of platelets from {http://www.heparin-law.com/adverse_heparin_reactions.html}
    Heparin is one of the oldest drugs currently still in widespread clinical use. Its discovery in 1916 predates the establishment of the Food and Drug Administration of the United States, although it did not enter clinical trials until 1935. from {http://newjournal.kcsnet.or.kr/main/j_search/j_download.htm?code=B091242}
    The enzymes traditionally used to digest heparin or HS are naturally produced by the soil bacterium Pedobacter heparinus (formerly named Flavobacterium heparinum). from {http://stanford.wellsphere.com/wellmix360/pedobacter}
    http://en.wikipedia.org/w/index.php?title=Anhydromannose&action=edit&redlink=1 from {http://www.boinc.org/heparin-sodium/}
    None of these sites shows a GFDL or Commons type licence. All but boinc.com show copyright notices. As a result of this I am going to immediately de-list this artcile. I have not examined every phrase, but it appears that there is little in the article that is copyuright free.
    As commented below by User:MarcoTolo these in fact appear to be copyright violations in the other direction, so I am happy to cancel that concern.
    Prose concerns:
    There are a number of single or double sentence paragraphs, please try to organise better.  Not done
    Heparin dose can be effectively managed using techniques like Sonoclot As the Sonoclot article does not exist, I am left unclear by this statement, please expand and explain. As a general point, wikilinking alone is not enough when introducing unfamiliar terms. This is a good example of where a brief explanation would be good, even if there was a Sonoclot article. Commensense of course applies, I believe that the general reader aimed at should be familiar with at least high school science.  Done this sentence has been removed
    For a full discussion of the events surrounding heparin's discovery see Marcum J. (2000), better to say something like: Marcum's paper on "The origin of the dispute over the discovery of heparin" gives a full discussion of heparin's origin. And then of course the cite. Done
    Other uses/information: WP:MOS suggests turning bulleted lists into prose where possible.  Not done
    Dircet html links such as like Non-weight-based heparin dose adjustment and Weight-based-heparin dose adjustment and 1HPN should be avoided and replaced by prose and cites.
    Ok, the prose needs some tweaking as noted above.
  2. It is factually accurate and verifiable.
    a (references): b (citations to reliable sources): c (OR):
    The article is well referenced, but I found a number of dead links, and fixed some others. I tagged the links, but couldn't find archived versions at the Internet Archive, which may be temporarily down. Not done One other citation (#51)[2] doesn't support the statement. Not done Probably somewhere else on the site.
    Sources where accessible were ok and RS.
  3. It is broad in its coverage.
    a (major aspects): b (focused):
  4. It follows the neutral point of view policy.
    Fair representation without bias:
  5. It is stable.
    No edit wars, etc.:
  6. It is illustrated by images, where possible and appropriate.
    a (images are tagged and non-free images have fair use rationales): b (appropriate use with suitable captions):
  7. Overall:
    Pass/Fail:
    The copyright concerns listed above are sufficient for immediate de-listing. However I will notify major contributors and projects for a response. On hold for three days. Jezhotwells (talk) 20:06, 27 February 2010 (UTC)[reply]
    OK, I am pleased that the copyvio thing was a red herring, although it would appear that in fact this ought to be reported to Wikipedia as we are not properly attributed on many of these sites. The remaining prose and dead links need addressing so on hold for seven days. Hopefully things can be fixed up by then. Jezhotwells (talk) 23:29, 2 March 2010 (UTC)[reply]
    Some progress has been made but there are still outstanding issues, so I am de-listing. Please bring back to WP:GAN when these have been fixed. Jezhotwells (talk) 22:36, 9 March 2010 (UTC)[reply]

Copyvio concerns

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After running the Copyright Violation Detector tool (output below; original job run here) I'm beginning to suspect the copyvio is the other direction (i.e. non-free use of Wikipedia material):

CVD output

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Output of Copyright Violation Detector (3/2/2010):

Heparin

  • Heparin, a highly-sulfated glycosaminoglycan, is widely used as an injectable anticoagulant, and has the highest negative charge density of any known biological...
  • molecule. It can also be used to form an inner anticoagulant surface on various experimental and medical devices such as test tubes...
  • and renal dialysis machines. Pharmaceutical grade heparin is derived from mucosal tissues of slaughtered meat animals such as porcine (pig) intestine or...
  • Although used principally in medicine for anticoagulation, the true physiological role in the body remains unclear, because blood anti-coagulation is achieved mostly...
  • into the vasculature at sites of tissue injury. It has been proposed that, rather than anticoagulation, the main purpose of heparin is...
  • Heparin is a member of the glycosaminoglycan family of carbohydrates (which includes the closely-related molecule heparan sulfate) and consists of a variably-sulfated...
  • The main disaccharide units that occur in heparin are shown below. The most common disaccharide unit is composed of a 2-O-sulfated iduronic...
  • ester and amide sulfate groups are deprotonated and attract positively-charged counterions to form a heparin salt. It is in this form that...
  • One unit of heparin (the "Howell Unit") is an amount approximately equivalent to 0.002 mg of pure heparin, which is the quantity required...
  • The three-dimensional structure of heparin is complicated by the fact that iduronic acid may be present in either of two low-energy conformations...

In particular

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  • The hanging chemical names (without the corresponding images) on the Medic8.com page seem suspicious (also an issue on the boinc.com version of the same page);
  • The phrase "Heparin is one of the oldest drugs currently still in widespread clinical use. Its discovery in 1916 predates the establishment of the United States Food and Drug Administration, although it did not enter clinical trials until 1935." has been in the Wikipedia version since at least 2008-06-11 (per this version), while the Bulletin of the Korean Chemical Sociey paper is listed as having been received 2009-05-31;
  • The above is also true for this link dated 2008-10-14;
  • Refreshingly, the Wellsphere link actually does cite Wikipedia (go figure);

There are other links I didn't follow, but given the above I suspect we have a whole host of sites (and at least one academic paper!) blatantly ripping-off WP content. -- MarcoTolo (talk) 22:47, 2 March 2010 (UTC)[reply]

Thanks for sorting this out, I am glad that I was wrong. I will use the copyvio tool in future. Jezhotwells (talk) 23:30, 2 March 2010 (UTC)[reply]

Recent edit adding pharmacology information

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This edit[3] added information saying excretion was done in urine. Perhaps so, after metabolism. I'm not up on pharmacology but this source says "Second, when used in clinical doses, UFH is not cleared by the kidneys..." [4] Biosthmors (talk) 17:24, 10 February 2012 (UTC)[reply]

Administration

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"Heparin is given parenterally because it is not absorbed from the gut, ..." Surely that should be, "Heparin is not given parenterally ...." — Preceding unsigned comment added by Will Somers (talk • contribs) 14:14, 29 October 2014 (UTC)[reply]

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Historical review

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doi:10.1111/jth.13555 JFW | T@lk 11:13, 28 December 2016 (UTC)[reply]

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Sepsis

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Heparin more than anticoagulant doi:10.1111/bjh.14885 JFW | T@lk 12:30, 26 October 2017 (UTC)[reply]

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What does this have to do with the topic in question?

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User:Petergans


"The interaction of metal ions and coordination compounds with biologically relevant oligosaccharides has been named Metalloglycomics. Interactions between glycosaminoglycans and proteoglycans and various platinum anti-cancer reagents have been reviewed.[1]"

Doc James (talk · contribs · email) 14:09, 27 February 2018 (UTC)[reply]

Section 1 of the article: "Introduction. Metalloglycomics, Heparin and Heparan sulfate".
Section 3 "Interaction of Metal Ions with glycosaminoglycans"
Section 4 "Interaction of coordination compounds with glycosaminoglycans". It also includes a section on non-covalent Heparan Sulfate binding. Petergans (talk) 15:29, 27 February 2018 (UTC)[reply]
Section 5 "Use of Metal Complexes in Heparin Analysis"

FYI. I am a retired academic (Leeds University, Department of Inorganic Chemistry), with a long-standing interest in bio-inorganic chemistry. I have a copy of the book and read each article before deciding if a WP citation is warranted. My long-term aim has been to improve the quality and robustness of those WP articles which lie within my professional area of interest, such as equilibrium chemistry, an article I created. Petergans (talk) 15:29, 27 February 2018 (UTC)[reply]

This is off topic "The interaction of metal ions and coordination compounds with biologically relevant oligosaccharides has been named Metalloglycomics."
This statement does not mean much / is undue weight "Interactions between glycosaminoglycans and proteoglycans and various platinum anti-cancer reagents have been reviewed." Looks like an advertisement to the book in question,.
So I have removed again. Doc James (talk · contribs · email) 11:58, 28 February 2018 (UTC)[reply]

The unwarranted slur on my reputation, which I have highlighted above should be removed. I have no connection of any kind with the publisher. Note that this "book" contains only review articles which have been specifically commissioned by the editors, from leading authorities like Prof. Lippard from M.I.T. Petergans (talk) 10:27, 1 March 2018 (UTC)[reply]

References

  1. ^ Farell, Nicholas P.; Gorle, Anil K.; Peterson, Erika J.; Berners-Price, Susan J. (2018). "Chapter 4. Metalloglycomics". In Sigel, Astrid; Sigel, Helmut; Freisinger, Eva; Sigel, Roland K. O. (eds.). Metallo-Drugs:Development and Action of Anticancer Agents. Vol. 18. Berlin: de Gruyter GmbH. pp. 109–140.

Primary use

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The primary use of the term is for the medication. We have the article on Heparan sulfate. The less common meaning can be introduced latter in the lead. Doc James (talk · contribs · email) 03:02, 5 June 2019 (UTC)[reply]

Pharmacology of heparin

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2016, only 66 pages doi:10.1124/pr.115.011247 JFW | T@lk 21:40, 26 October 2020 (UTC)[reply]

Heparin is antiviral. covid-19

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You can find a bit information with Google search

enoxaparin OR heparin antiviral OR virus

But I don't know how promising is this for covid-19 and other viruses.

--46.132.37.34 (talk) 23:19, 8 January 2021 (UTC)[reply]

AT?

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"Since heparins depend on the activity of AT". In the beginning of the article. What is AT? It should be defined and linked. 81.185.172.172 (talk) 11:59, 22 November 2021 (UTC)[reply]

Regarding the General Structure

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I believe that the figure showing the General Structure of Heparin is erroneous. Namely, the leftmost saccharide (which I believe to be 2-O-sulfo-α-D-glucuronic acid) is not one of the possible saccharides mentioned later in the article (GlcA, IdoA(2S), GlcNAc, GlcNS, GlcNS(6S), or even the rare GlcNS(3S,6S)). The closest "valid" saccharide to the one shown in the figure would be IdoA(2S). The difference being that the COO- and OSO3- groups should be on the same side of the ring. I imagine the error stems from a desire to create a more readable structure, but as far as I can tell, is nonetheless invalid. G.Lazarski (talk) 04:06, 10 May 2023 (UTC)[reply]

Medical use

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The "medical use" section states that heparin allows the clot lysis to occur but this is not correct and is in conflict with the "mechanism of action" subsection that correctly explains how heparin works as an anticoagulant. 70.245.42.45 (talk) 20:58, 1 August 2024 (UTC)[reply]

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