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User:Nikos 1993/sandbox/Drugbox — changes:

Nikos 1993 (talk) 01:33, 21 June 2012 (UTC)

I'm rather confused by your proposed changes. The material in your sandbox doesn't seem to correspond to the template's text, nor the documentation page (which is not protected). Maybe I'm completely missing it, but you have to take pity on us responders by stating exactly where the material you are suggesting should go, and a bit about the reason for the change. Can you explain more clearly? Wherever this is to go, for example, why would we be adding 6 categories that do not exist?--Fuhghettaboutit (talk) 03:09, 21 June 2012 (UTC)
Currently only AU, CA, US and UK legal statuses are in the template, and the "most international" UN ones are not. Proposed changes fix this, and also add EU regulations and US precursor tables. Nikos 1993 (talk) 10:54, 21 June 2012 (UTC)
The categories are to be created. Nikos 1993 (talk) 12:58, 21 June 2012 (UTC)
Could you please incorporate your suggested changes in Template:Drugbox/sandbox? You can then re-request the edit of the protected drugbox. Thanks. --Dirk Beetstra T C 05:28, 21 June 2012 (UTC)
Template:Drugbox/sandbox (diff, examples of use) Nikos 1993 (talk) 10:32, 21 June 2012 (UTC)
I would suggest waiting for a day to see if any of the Pharmacology project people have any comment on this, as they are fairly active here. — Martin (MSGJ · talk) 15:53, 21 June 2012 (UTC)
Omg you're so overly cautious as if I'd be proposing some hoax. See the sources and believe it's a good will edit request, with no factual mistakes:
(DEA Diversion may not work for some non-US visitors, use eg. Zend Proxy)
Nikos 1993 (talk) 18:54, 21 June 2012 (UTC)
Thanks for adding you proposed changes to the sandbox and for creating the examples. I think we now have a much better idea what you are proposing. The issue is not whether this is a hoax or not (I firmly believe what you are proposing is not a hoax), but rather whether the added links are relevant and not excessive. Since the links are a reasonable expansion to other jurisdictions, the would appear to be reasonable. However I have a question about both the proposed and existing "legal status" links (see for example the drugbox in Oxycodone). These are internal wiki links and these links do not necessarily provide adequate sources that the drug in question is actually controlled in the jurisdiction in question. Ideally the the links should be to external reliable sources that support the stated "legal status". So the question I have is are there better external reliable sources we can link to? Boghog (talk) 19:59, 21 June 2012 (UTC)
The links in my last post are complete list of 100% reliable sources for current legal status of ALL substances controlled in UN, US and EU. www.deadiversion.usdoj.gov is a US government site, eur-lex.europa.eu publishes EU laws, www.incb.org is UN International Narcotics Control Board. Nikos 1993 (talk) 20:32, 21 June 2012 (UTC)
Maybe something like this: <sup><span class="plainlinks">[http://www.deadiversion.usdoj.gov/schedules/orangebook/h_chemlist_listorder.pdf <nowiki>[check]</nowiki>]</span></sup> foobar[check] Nikos 1993 (talk) 20:46, 21 June 2012 (UTC)
Or simply these links would be in wiki pages about conventions and laws controlling these substances. Nikos 1993 (talk) 20:50, 21 June 2012 (UTC)
Exactly. Either way, it will take some work to properly document the legal status. Boghog (talk) 21:05, 21 June 2012 (UTC)
But I have just done this work. And see the current version of the template - I didn't introduce anything new, I simply extended existing solution to UN and EU schedules. Nikos 1993 (talk) 21:10, 21 June 2012 (UTC)

Is anyone going to deploy these changes? Everyone only complains like it was some revolution which needs long discussions, while it is simply extending existing solution to UN and EU regulations! (And I have experience with MediaWiki syntax, so I'm sure I didn't break existing code). Nikos 1993 (talk) 23:39, 21 June 2012 (UTC)

The proposed changes look OK to me. We are just being a little cautious since this template is displayed in a large number of drug articles. We are also allowing time for others to express an opinion.
I also have one minor suggestion. While the displayed link names are abbreviated, they are still somewhat long. Could these be shortened further? For example "Narcotic Schedules" → "Narc. Sched." Boghog (talk) 17:54, 22 June 2012 (UTC)
I personally think current length is OK. Meanwhile I added complete list of substances scheduled by Single Convention on Narcotic Drugs. Nikos 1993 (talk) 19:35, 22 June 2012 (UTC)
Filled Convention on Psychotropic Substances#List of controlled psychotropic substances too. Nikos 1993 (talk) 20:00, 22 June 2012 (UTC)
United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances#List of controlled drug precursors also completed. Nikos 1993 (talk) 20:27, 22 June 2012 (UTC)

information Administrator note There have been no further comments so I plan to implement this shortly. Nikos, can you confirm that the latest (23 June) version in the sandbox is ready to deploy? — Martin (MSGJ · talk) 18:13, 27 June 2012 (UTC)

Disabled request as no response from OP. — Martin (MSGJ · talk) 21:21, 29 June 2012 (UTC)
Re-requesting. Yes, I can confirm. Nikos 1993 (talk) 12:39, 30 June 2012 (UTC)
Deployed that version. Sorry this took so long. Could you update the documentation? — Martin (MSGJ · talk) 19:21, 1 July 2012 (UTC)
I added another change - separation of controlled drug status and prescription status. For now the 23 June version is OK, but later changes are to be discussed / worked out. Nikos 1993 (talk) 18:38, 30 June 2012 (UTC)

SMILES problem

When I clink the SMILES in Pingyangmycin, the drugbox is expanded to the width of the whole screen. Anyone can fix that? THX!--Jsjsjs1111 (talk) 22:01, 9 July 2012 (UTC)

We've been having the same problem with InChIs, but no one has found a solution yet. Sorry. --ἀνυπόδητος (talk) 06:32, 10 July 2012 (UTC)
see Template_talk:Chembox#Line_wrap_problem_revisited - there is something really strange in how tables are parsed (on Wikipedia), IMHO, the only REAL solution is if someone manages to enforce that a box is NEVER wider than (e.g.) 25% of the pagewidth - if the string is longer than the pagewidth, it breaks it where necessary at a random place, but it seems impossible to say 'make sure that this string on display is never longer than 40 characters, even if that means that you have to break it in a random place. One other option is to randomly break it manually - which breaks outgoing searches/incoming searches/external-database connectivity (e.g. this display based on SMILES works, but if you break the SMILES in Benzene by inserting a random space, you get this effect ("ERROR opening http://cactvs.nci.nih.gov/chemical/structure/c1cc+ccc1/file?format=sdf&get3d=True -- c1cc+ccc1 could not be loaded."). Not displaying the SMILES (just have it as a non-used parameter in the box) makes it more difficult to really access the string 'c1ccccc1', which some people may want to copy-paste into search engines to search for other datasources, and since it is not parsed into the text, Google would not find the wikipedia article benzene (does not get a high rank anyway based on SMILES, but it is for me third when looking in google for the benzene InChI "InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H"). Per Anypodetos: Sorry. --Dirk Beetstra T C 06:48, 10 July 2012 (UTC)
I suppose style="max-width: 25%" has been tried? --ἀνυπόδητος (talk) 07:57, 10 July 2012 (UTC)
I don't think it would work.--Jsjsjs1111 (talk) 10:37, 10 July 2012 (UTC)
I indeed think we tried quite some things - but just in case we missed something, please try it on a sandbox - if the enforcing of a max percentage works, it should work for everyone (Java enabled or not). I'd really like to see it (better than the randomness that Template_talk:Chembox#Line_wrap_problem_revisited displays (note that one of the boxes is 50% for some stupid reason, even while the breaking hyphen is somewhere else). --Dirk Beetstra T C 11:02, 10 July 2012 (UTC)

I've solved this in the chembox on Chinese wikipedia (the template is not fully protected there). Just need to add "max-width:22em; word-wrap: break-word". However, idk how to deal with it in drugbox.--Jsjsjs1111 (talk) 14:16, 10 July 2012 (UTC)

For drugbox I think we need another template instead of {{Collapsible list}}. I've solved it on chinese wikipedia, using a new template with the attributes above called zh:Template:Collapsible list for drugbox.--Jsjsjs1111 (talk) 14:38, 10 July 2012 (UTC)

It works by adding | liststyle = max-width:22em; word-wrap:break-word; as the first parameter (although this shouldn't be relevant) to the two {{Collapsible list}}s (lines 506 and 509 for SMILES and InChI, respectively), which I hereby request. Working example see User:Anypodetos/Sandbox2, where the template User:Anypodetos/Sandbox is transcluded. The mentioned param is included for SMILES but not for InChI. Thanks --ἀνυπόδητος (talk) 18:29, 11 July 2012 (UTC)

Done, see here, although it would have been more conventional to amend the page Template:Drugbox/sandbox so that any admin could merely copy one to the other. Luckily I knew what this was about, having done this earlier today. --Redrose64 (talk) 19:43, 11 July 2012 (UTC)
Thanks! The sandbox currently contains code that has been (somewhat) discussed above, but without clear consensus; I just didn't want to delete that code. --ἀνυπόδητος (talk) 20:09, 11 July 2012 (UTC)
Thank you very much! However I think it would be better if "21em" instead of "22em" is used here, as the {{Collapsible list}}s works differently.--Jsjsjs1111 (talk) 21:00, 11 July 2012 (UTC)

Edit request on 20 August 2012

Again, it's about the SMILES problem above. Using | liststyle = word-break:break-all; instead of | liststyle = max-width:22em; word-wrap:break-word; would makes it looks better when the image is wider than the original drugbox size, see the sandbox version and the current version.

Jsjsjs1111 (talk) 12:28, 20 August 2012 (UTC)

Literally only a few minutes ago this edit showed on my watchlist, and I happened to glance at Template talk:Chembox#Line wrap problem revisited. Having been involved then, I'm wondering how it will affect that problem? --Redrose64 (talk) 12:53, 20 August 2012 (UTC)
Well, if we use | liststyle = max-width:22em; word-wrap:break-word;, when the drugbox is wider than the original drugbox size, the smiles and inchi section would still have the fixed width of the original drugbox size. Using | liststyle = word-break:break-all; would solve this problem. However the chembox should not be changed since | liststyle = word-break:break-all; would might break down the words in the IUPAC name.--Jsjsjs1111 (talk) 14:09, 20 August 2012 (UTC)
Just to be clear, since there's a lot of difference between sandbox and live - this only affects a single line, the one for SMILES - the InChI line isn't to change? --Redrose64 (talk) 16:11, 20 August 2012 (UTC)
Could you change both of them? If you are not sure -- I've just edited the sandbox, thus you can just copy it. Thanks!--Jsjsjs1111 (talk) 16:39, 20 August 2012 (UTC)
Done --Redrose64 (talk) 18:48, 20 August 2012 (UTC)
Thank you very much!--Jsjsjs1111 (talk) 18:57, 20 August 2012 (UTC)

Licence data

The params licence_EU and licence_US don't seem to work – the external links they produce end up on the EMA/FDA search pages. Any idea how to fix this? --ἀνυπόδητος (talk) 17:28, 14 January 2013 (UTC)

bot expansion/maintenance of drugbox

I recently started a discussion at WP:PHARM around a proposal to expand the information in this template and to maintain this information using a bot. The discussion began here, and has since moved over to User:ProteinBoxBot/Phase_3. I'd personally like to focus on adding new fields for data that is not already in the drugbox, but we're happy to take on the role of maintaining existing parameters as well. In any case, feedback is welcome... Cheers, Andrew Su (talk) 05:43, 21 May 2013 (UTC)

Equianalgesia parameter

This template needs a parameter for equianalgesia relative to morphine.   — C M B J   06:04, 22 May 2013 (UTC)

Physical data - flash and decomposition points

There is no option for flash or decomposition points in the physical data field. This seems like a fairly big oversight for several drugs that are vaporized as a method of administration. 3AlarmLampscooter (talk) 02:37, 2 July 2013 (UTC)

Clinical data -- Additional Helpful Fields

Currently in the drugbox there is no information as to standard dosage ranges and frequency of dosing and I believe to add such a field would be helpful.Fuse809 (talk) 14:31, 30 September 2013 (UTC)

On the surface I would agree but dosage varies wildly depending on ROA, tolerance and the individual and I don't think this variation would be well captured in a small space like this. Testem (talk) 23:38, 25 December 2013 (UTC)

Requested move

The following discussion is an archived discussion of a requested move. Please do not modify it. Subsequent comments should be made in a new section on the talk page. No further edits should be made to this section.

Moved. The arguments in favor of uniformity counter the non-issue of the old name continuing to be used as a redirect. Given the way that templates work, there is no substantive difference between having one title or the other, and the arguments for uniformity in template naming support the name flip. bd2412 T 14:10, 23 October 2013 (UTC)

Template:Drugbox → Template:Infobox drug – This template is already an infobox, as is shown by its categorisation under Medicine infobox templates, and the title should also reflect this. There are thousands of infoboxes, and using a consistent naming scheme helps with maintenance and administrative tasks. eh bien mon prince (talk) 15:36, 30 September 2013 (UTC)

  • Comment this template is using the old naming style, prior to the introduction of "infobox" -- 65.92.181.39 (talk) 05:55, 1 October 2013 (UTC)
  • I don't see the problem. It will result in a lot of edits to a lot of pages which are, basically, useless. Moreover, everyone who is used to the old naming will have to get used to the new naming, and only the few new editors who use this will see the benefit (if any) of a more consistent naming. oppose. --Dirk Beetstra T C 09:11, 1 October 2013 (UTC)
The current name will continue to exist as a redirect, so no edits will be necessary, or getting used to new names.--eh bien mon prince (talk) 09:26, 1 October 2013 (UTC)
That makes it even less necessary .. we have thousands of articles then using a redirected template, and a couple with the new - which is only going to be confusing. Moreover, most people will start a drugbox on an article by taking one from another page, pasting it into a new page and adapt it. That gives a high chance it will be the old name. --Dirk Beetstra T C 10:41, 1 October 2013 (UTC)
Redirects are cheap, and using the 'infobox' prefix does make things considerably easier for the (admittedly few) people who are part of the Infobox WikiProject or work with them in other ways, and that should cause little or no inconvenience to other users, so I hope you'll reconsider.--eh bien mon prince (talk) 11:31, 1 October 2013 (UTC)
Redirects are cheap .. that is why Template:Infobox drug is already redirecting to Template:Drugbox. The convenience is there, so I still don't see the use of swapping the place of it. --Dirk Beetstra T C 12:48, 1 October 2013 (UTC)
Bots, scripts and special pages like Special:PrefixIndex can only either find all redirects or none of them, regardless of their use, and out of 2,135 infoboxes that appear in Wikipedia:List of infoboxes there are just five which are not using the Infobox prefix. Using the right prefix makes it easier to find the right infoboxes, without having to go through thousands of unused redirects. Moving this template might be an improvement only for the few people who habitually work with infoboxes, but if the inconvenience for other users is not so great it would still be worth doing, I think.--eh bien mon prince (talk) 14:58, 1 October 2013 (UTC)
My bot, which is doing just that on drugboxes, is finding all of them just fine - it is easy to resolve that by script, bot, etc. As does the script that collects the transclusion count on that page you link. I still don't see a compelling reason, but maybe others will see differently. --Dirk Beetstra T C 08:02, 2 October 2013 (UTC)
  • Oppose. I don't see any real value in making this change ("improvement only for a few people", as you say), and it is likely to cause confusion. -- Ed (Edgar181) 14:48, 3 October 2013 (UTC)
It won't cause any confusion, redirects from the previous name will continue to work.--eh bien mon prince (talk) 11:37, 6 October 2013 (UTC)
  • Support As usual, template names don't matter a great deal. But I don't see any reason not to standardize this one with other infoboxes, nor any real evidence of harm that could result from this move. --BDD (talk) 20:38, 7 October 2013 (UTC)
  • Oppose – I'd be fine with either title, but I don't see a reason to change it. There's {{taxobox}}, which doesn't have a preceding "infobox". --Article editor (talk) 22:23, 16 October 2013 (UTC)
  • Support. Agreeing with others that it's really no big deal either way, the balance for me nevertheless swings decidedly in favor of the move for consistency and attendant ease on a few who concentrate in the area, while the harm in making the move appears entirely illusory.--Fuhghettaboutit (talk) 23:40, 22 October 2013 (UTC)
  • Support. The fact the some editors don't see a reason to change does not mean that change is bad. Since most of these were renamed a while ago and since renaming would follow existing conventions, I would really like to see a sound argument about why we should not do this. It breaks nothing and follows convention. How can that be wrong? Vegaswikian (talk) 00:14, 23 October 2013 (UTC)
The above discussion is preserved as an archive of a requested move. Please do not modify it. Subsequent comments should be made in a new section on this talk page. No further edits should be made to this section.

Legality fields

When multiple legality fields are used (e.g. legal_US and legal_UK), their contents run together. Instead, they should be separated by a line break, so that the distinction between localities is made clear. —Gordon P. Hemsley→✉ 17:49, 1 June 2013 (UTC)

Do we have examples of what these two different formatting styles look like? Doc James (talk · contribs · email) (if I write on your page reply on mine) 18:15, 1 June 2013 (UTC)
See, e.g., propranolol for what it looks like now (which is rather hard to read). It all just flows together, with a combination of regular text and smaller text in parentheses (representing the country). —Gordon P. Hemsley→✉ 19:13, 1 June 2013 (UTC)
Okay sounds good support the change. Doc James (talk · contribs · email) (if I write on your page reply on mine) 21:09, 1 June 2013 (UTC)
Nothing wrong with running together on as few a number of lines as possible. Rather than a line break for each, why not a separating "," comma ? David Ruben Talk 23:43, 2 June 2013 (UTC)
That is indeed an alternative, but I don't think it would provide much more separation than is already present. I don't see why we need to aim for "as few a number of lines as possible". —Gordon P. Hemsley→✉ 14:46, 3 June 2013 (UTC)
reducing white space is useful as helps reduce need for readers to scroll down a page, and reduces sheets of paper when the articles inevitably printed off (how else will patients come in clutching internet stuff I should read for the "correct" treatment, with material I happen to have contributed in writing, have followed the guidelines already and alternatives they either previously tried, or are already taking, or don't have the condition in question) David Ruben Talk 03:29, 4 June 2013 (UTC)
You could also use a bullet "•" as your list separator. I think that WP:ACCESS (or is it the MOS page on lists?) has something about a horizontal list, which might also be appropriate. WhatamIdoing (talk) 03:30, 11 June 2013 (UTC)

I'd like to fix this long-standing annoyance.

The bullet and flatlist styles are useful when you can actually get more than one item on a line within the width of the infobox. In the case of the legal status, though, that mostly isn't possible, and the current run-together style is just confusing. The current hydrocodone article looks like:

Legal status    Controlled (S8) (AU)
Schedule I (CA) Class A
(CD) (UK) Schedule II (US)

Try to quickly determine the exact UK classification (Class A (CD)).

I'd like it to look like:

Legal status    Controlled (S8) (AU)
Schedule I (CA)
Class A (CD) (UK)
Schedule II (US)

or, since one normally thinks about looking for the status for a given country, placing the key to the left of the value:

Legal status    AU: Controlled (S8)
CA: Schedule I
UK: Class A (CD)
US: Schedule II

An added benefit, per the current MOS, is that (invisible) list markup will be used, which is the more correct technical way to do it.

Thoughts? —[AlanM1(talk)]— 09:05, 4 September 2014 (UTC)

I don't find any list markup above, invisible or otherwise; it's all marked up as separate table rows, which is an accessibility problem. Better would be to use a plainlist; the {{ubl}} template is available for this:
Legal status   
Legal status   
I prefer the second version, where the country codes come first. You can also see {{ubl}} in action at LB&SCR A1X Class W8 Freshwater. --Redrose64 (talk) 11:33, 4 September 2014 (UTC)
Yes – my intent was to use {{Unbulleted list}} (or maybe its internals). What I did above was just for sake of a quick mockup here (I didn't want to deal with possible formatting differences). —[AlanM1(talk)]— 12:21, 4 September 2014 (UTC)
made some changes as suggested, so done? Frietjes (talk) 17:09, 6 September 2014 (UTC)

Additional atom types

Any objections if I add Al, Ca, Li, and Mg to the Formula field? Per Category:Drug pages needing formula fontification, there are a couple of pages each that would need these. --ἀνυπόδητος (talk) 20:23, 6 November 2013 (UTC)

 Done --ἀνυπόδητος (talk) 13:04, 11 November 2013 (UTC)

Box too wide

In the article Etorphine, the {{Drugbox}} is displayed much too wide; this messes up the whole page. By trial and error I have tracked the problem to the parameter |StdInChI=. Unfortunately, I do not understand what this is (I am not a chemist), so have no idea what would be the proper way to break this up. Hopefully, somebody else knows. HairyWombat 04:27, 22 December 2013 (UTC)

Hm. It displays correctly for me. What system and browser are you using? Have you got JavaScript enabled? --ἀνυπόδητος (talk) 08:44, 22 December 2013 (UTC)
I am using Opera 10.10 (which is old) with JavaScript. The page displays correctly for me when I use a more recent version of Opera. Not sure why it displays incorrectly with my old browser, but this is obviously not a big deal after all. HairyWombat 05:17, 25 December 2013 (UTC)

Additional relevant bits of chemical information

Hi, people. I feel the need to request new bits of chemical information to be added to the drugbox, namely the following:

  • Partition coefficient — log P. The reason why is quite simply it gives an approximation as to the lipophilicity of the drug in question. The lipophilicity is very important when one is considering whether the drug is likely to be capable of penetrating phospholipid bi-layer cell membranes and hence also likely to be able to cross the blood-brain barrier. I will admit that water solubility does give some idea as to a drug's lipophilicity but as much as the partition constant.
  • Acid dissociation constant — pKa. Important in that the absorption of a drug heavily depends on its pKa and its lipophilicity.

I would also think adding some dosing information would be nice but I understand (but don't necessarily agree) that this is to avoid the use of Wikipedia as a source of personal medical advice. Fuse809 (talk) 10:42, 17 October 2013 (UTC)

I am wary of adding parameters such as log P and pKa to the drugbox. Please note that the drugbox is meant to be used for compounds that have at least reached clinical trials, not pre-clinical drug development candidates. I agree that log P and pKa are very useful for predicting various pharmacokinetic (PK) properties. But for drugs that already in the clinic, there is no longer a need to predict PK because it has been measured experimentally. Furthermore if a drug has an intracellular target, then it by definition it must have been able to pass the cell membrane. The {{chembox}} already has log P and pKa and I would argue that for preclinical drug candidates, the chembox is more appropriate than the drugbox.
Also concerning doses, WP:PHARMOS explicitly states that dosing information should not be included, except under very specific circumstances. Furthermore dosing can vary considerably depending on the indication, age of the patient, etc. Hence this type of information can become very messy and not well suited for inclusion into an infobox. For these reasons, adding dosing information to the drugbox IMHO is not a good idea. Boghog (talk) 21:15, 17 October 2013 (UTC)

Blood-brain penetrability data isn't always available (and in my experience is rather rare) and hence there is still value to log P. Fuse809 (talk) 01:11, 18 October 2013 (UTC)

If a drug has a CNS therapeutic or side effect, by definition it must be getting into the CNS. Why try to predict a parameter for which there is already clinical data? Furthermore, polar surface area is probably a better predictor of BBB penetration than log P. Finally while log P increases, brain exposure may increase, but the at same time, the free fraction decreases. Hence while a lipophilic drug may have high CNS exposure, it may not be available to bind to its biological target (see for example PMID 19764786). Boghog (talk) 06:39, 18 October 2013 (UTC)

Yes if it has effects in the CNS it must cross the BBB but the extent is where log P comes in. Amisulpride, for instance, the antipsychotic isn't very lipophilic (low log P) and hence while it has CNS effects it has significantly more prominent peripheral effects such as hyperprolactinaemia. True polar surface area is a better predictor and hence I'd be glad to substitute it for log P if you so desire. As for its plasma binding well that's what the protein binding part of pharmacokinetic data is for. Fuse809 (talk) 10:47, 18 October 2013 (UTC)

If clinical CNS effects are observed, it gets into the CNS, period. There is no need to predict it. Hence there is no need to add log P or PSA to the drugbox. The free fraction in the CNS is NOT the same as the free fraction in serum. Knowing serum protein binding tells you nothing about free fraction in the CNS. Serum contains high levels protein binding proteins such as albumin that unless there is a break down of the BBB are not present in the CNS. Conversely the CNS due large amouns to myelin is a much more hydrophobic environment than blood serum. Consequently the use of logP to predict the extent of CNS exposure can be very misleading. Boghog (talk) 11:07, 20 October 2013 (UTC)

Log P/PSA is good to have just because usually its a good predictor of CNS penetrability and activity. Yes there are other variables that can affect it such as protein binding to myelin but usually log P/PSA is a decent predictor. If CNS effects are observed it does penetrate the BBB but as I gave with the example of amisulpride the extent is relevant. If you go through all the CNS-affecting drugs in clinical practice blood-brain penetrability is very well predicted by log P/PSA. For instance fentanyl has a much higher log P (~3.89 vs. ~0.5) and lower PSA (23.55 Â2 vs. 52.93 Â2) than morphine and consequently it is far (x100) more potent an analgesic than morphine and produces fewer peripheral adverse effects (e.g. constipation, nausea, vomiting, pruritus, etc.). I will acknowledge that it isn't a perfect predictor but neither is any bit of clinical data seeing how there are individual differences. Fuse809 (talk) 13:57, 20 October 2013 (UTC)

Why do we need a predictor when we have experimental data? Furthermore log P is a lousy predictor of CNS activity. To understand why, you need to read PMID 19764786. LogP is a useful predictor of the total brain/plasma ratio. But this is only half the story. In order to bind to its target, it also must be solution as measured by free fraction. Increasing logP will tend to increase the total brain/plasma ratio but will also decrease the free fraction in the CNS. For this reason, looking only at logP can be very misleading. Boghog (talk) 15:03, 20 October 2013 (UTC)
Concerning the comparison of morphine with fentanyl, the former is a P-glycoprotein substrate where the later is not (see PMID 11964599). Hence morphine but not fentanyl is actively transported out of the brain. PSA is directly proportional to the number of heteroatoms. P-glycoprotein substrates also tend to have larger number of heteroatoms. This in part explains why PSA tend to be better predictor of CNS acidity than logP. Boghog (talk) 20:08, 20 October 2013 (UTC)

If you have experimental data on the penetrability of every clinically-utilised drug across the BBB then you must have an unprecedentedly extensive resource and in such a case I consider it selfish that you're not sharing it with wikipedia by encorporating it into our articles. P-glycoprotein mustn't do this to morphine that efficiently as it still has central effects but nonetheless other morphine-like opioids such as oxycodone are significantly less lipophilic than fentanyl and hence are significantly weaker and have more prominent peripheral side effects such as emesis, constipation and pruritus. Plus ionic molecules like methylnaltrexone have poor BBB penetrability and has a significantly lower log P than its non-ionic counterpart, naltrexone. Fuse809 (talk) 04:51, 21 October 2013 (UTC)

Of course neither I nor anyone else has data on the penetrability of every approved drug. To repeat what I have said above, if CNS effects or CNS side effects are clinically observed, the drug by definition must be getting into the CNS.
Neither lipophilic driven passive transport nor PGP active transport is all or nothing. There are grey areas for both. Furthermore the assumption that the higher the logP, the better is wrong. There is an optimal logP range which has been estimated by Hansch to be 1.5–2.7 (see PMID 16489364) Therefore fentanyl (ClogP = 3.79) would appear to be too high for optimal CNS activity whereas morphine (ClogP = 1.19) and (ClogP = -0.98, XLogP3: = 1.2, ALOGPS = 1.03) would be too low. Oxycodone (PMID 17251015) is also a PGP substrate. All three drugs have logPs that appear to be non-optimal, but what distinguishes fentanyl from morphine and oxycodone is that the first is not a PGP substrate (fewer hydrogen bond acceptors) whereas the later two are PGP substrates (larger number of hydrogen bond acceptors). Because CNS activity is influenced by both passive and active transport, predicting CNS activity based physicochemical properties is very risky.
There are relatively few readers that would even be aware that such predictions can be made. Hence for the vast majority of readers, such information would have no value. For readers that can make such estimates, the drugbox contains links to DrugBank and to PubChem where logP, PSA, and pKa values are listed. Finally it should be obvious from the above discussion, that even if one has these physicochemical parameters, prediction are very difficult to make and to interpret. If these predictions are of interest, they should be included in the text supported by reliable sources while at the same time avoiding synthesis.
One final problem of listing physicochemical parameters such as logP and pKa is that there are many different methods for measuring or calculating these values and depending on which method is used, the estimates can differ significantly (see for example the logP estimates for morphine above). One in addition would need to specify what method was used to derive the parameter values. For making comparisons between drugs the parameters should be derived from the same method, but consistency is difficult if not impossible to enforce in Wikipedia. Boghog (talk) 21:10, 21 October 2013 (UTC)

Pregnancy cat.

Is it possible to have this as a removeable value? There are many novel drugs for which there is no pregnancy category, and having a ? in these cases serves only to unncessarily extend the drugbox. The substances in question often have little information known so the articles are short and huge drugboxes become especially unecessary. Testem (talk) 23:38, 25 December 2013 (UTC)

Agree. I've coded this in the sandbox. --ἀνυπόδητος (talk) 09:27, 26 December 2013 (UTC)
Boldly implemented. --ἀνυπόδητος (talk) 12:29, 28 December 2013 (UTC)
Wonderful, thanks Testem (talk) 08:48, 30 December 2013 (UTC)

LD50

Does anyone support adding an LD50 field? Exercisephys (talk) 23:01, 16 February 2014 (UTC)

Enantiomers

Infobox drug/Archive 10

Hi, I'd like to request that the drugbox, in analogy to the chembox which can currently manage this, becomes capable of showing the structure of the two enantiomers of a drug, side-by-side. Fuse809 (talk) 12:20, 2 April 2014 (UTC)

can you provide a specific example? Frietjes (talk) 17:18, 2 April 2014 (UTC)

Well tramadol is the drug I'd currently like to be able to do this with; the example I have of how the chembox can do this (albeit the two images side-by-side the way I want it aren't different enantiomers, just different 3D representations of the molecule) is on this page, 2C-P. Fuse809 (talk) 17:23, 2 April 2014 (UTC)

does the example presented here have the layout you want? not that this is the best way to do it, just trying to figure out exactly how you want the images presented. or do you just want the side-by-side images? Frietjes (talk) 17:28, 2 April 2014 (UTC)
It has the layout I want. The first image would be the great 2D image created by the Vaccinationist of the two enantiomers and then below it would be two 3D images of the two enantiomers in the same order (left-to-right) as the 2D image. Fuse809 (talk) 04:11, 3 April 2014 (UTC)
I updated the code and the example (imageL and imageR are now possible). let me know if you see any new bugs or problems. Frietjes (talk) 17:24, 3 April 2014 (UTC)
Thanks, it works perfectly. Fuse809 (talk) 06:59, 4 April 2014 (UTC)
Somewhat related, the PDB_ligand field has only one input (as far as I can see), but the PDB distinguishes enantiomers so only one form of an enantiomeric drug can be linked. For instance rosiglitazone and warfarin are given as R/S mixes and the PDB has both types (RGZ/BRL for rosiglitazone and RWF/SWF for warfarin). It would be great if multiple codes could be added here. A2-33 (talk) 23:08, 2 April 2014 (UTC)

Here are the two codes: R-tramadol and S-tramadol. Fuse809 (talk) 04:11, 3 April 2014 (UTC)

ChemSpider ID

I've updated the ChemSpider ID as follows, from:

| label46 = [[ChemSpider]] | data46 = {{#ifeq:{{{ChemSpiderID|}}}|NA||{{#if:{{{ChemSpiderID|}}} | <span class="reflink plainlinks nourlexpansion">[http://www.chemspider.com/Chemical-Structure.{{{ChemSpiderID}}} {{{ChemSpiderID}}}]</span>{{{ChemSpiderID_Ref|}}} }}}}

to

| label46 = [[ChemSpider]] | data46 = {{#ifeq:{{{ChemSpiderID|}}}|NA||{{#if:{{{ChemSpiderID|}}} | <span class="reflink plainlinks nourlexpansion">[http://www.chemspider.com/Chemical-Structure.{{{ChemSpiderID}}}.html {{{ChemSpiderID}}}]</span>{{{ChemSpiderID_Ref|}}} }}}}

This was in response to a request from the ChemSpider folks. The Drugbox was directing people to the disfavored link. --Rifleman 82 (talk) 13:45, 9 April 2014 (UTC)

Request for additional fields to account for isomerism

Hi, people, I've already requested left and right 3D image fields so as to account for the possible isomerism of drug molecules and now I'm requesting some additional fields to account for isomerism. Namely, I think ChemSpider ID, PubChem, SMILES, StdInChIKey and StdInChI should have an additional field one can provide it with so that it takes into account the isomerism of drug molecules. For instance, tramadol has two isomers (+) and (-) which have ChemSpider IDs of 31105 and 580887, respectively. Fuse809 (talk) 01:41, 6 May 2014 (UTC)

Tramadol is a bit of an exception in that both stereomers have (different) pharmacological actions. In most cases, one stereomer is just dirt (like a reaction by-product, only that it makes up 50% instead of 0.01%). I'm a bit concerned that giving both stereomers equal weight in the drugbox would mislead readers into thinking that both were important for the drug, e.g., as if it were a combination drug or the like. --ἀνυπόδητος (talk) 18:14, 6 May 2014 (UTC)
I can think of other drugs in which the two isomers are important to activity -- citalopram (albeit in this case it seems like the R-isomer reduces the activity of the S-isomer, but it's still important), tilidine, methadone and racecadotril. I don't see how adding additional isomers to the drugbox identifier fields will mislead readers, after all if this is likely to occur I think the fact that we usually include the two isomers in the structural images of the drugbox would be what misleads most readers. Fuse809 (talk) 01:44, 7 May 2014 (UTC)

Changes to infobox drug

I have prepared some changes, in {{Infobox drug/sandbox}}. See also {{infobox drug/testcases}}.

  • In label "Solubility in water", change link water to Properties of water unlink the word water. Per request at Chembox talk + follw up (see also below).
  • Removed small print from ℞-only → ℞-only. Found no reason or pressing habit to change fontsize in these situations.
  • For boiling point and melting point, use {{convert}} instead of hardcoded calculations to calculate F. Should not alter numbers, and keeps format the same over all enwiki. A temperature range entered with |melting_high=, will show using "... to ..." not a (more confusing) "–". Bad numerical input will be in the {{convert}} errorcategory.
(I add: "more confusing" when one ofg the numbers is negative -DePiep (talk) 17:13, 18 December 2014 (UTC)).
  • Removed unused subtemplate subheader (navbar & v-t-e box).
  • Allow captitalised |SMILES= as input for being the name (next to lowercase |smiles=).
  • Used whitespace internally to get more code overview.
  • Written some abbreviations in long.
  • All tracking categories only used in mainspace. (added -DePiep (talk) 17:28, 18 December 2014 (UTC))

I expect it can be put live shortly. -DePiep (talk) 23:43, 17 December 2014 (UTC)

I think it is misleading to link "solubility in water" to "properties of water" since "solubility in water" is as much a property of the drug as of water. As it is unnecessary to provide a link to water (a common term that everyone should immediately understand), it would be better to change the text to simply "solubility in water". Boghog (talk) 16:04, 18 December 2014 (UTC)
Good point, makes sense. More at the linked talk. -DePiep (talk) 17:11, 18 December 2014 (UTC)
Note: from now on, the issue of "link the word water?" is discussed at Chembox talk (its origin), not here. -DePiep (talk) 12:18, 2 January 2015 (UTC)
Green tickY The water link has changed again. See the linked talk for later developments. -DePiep (talk) 08:47, 10 January 2015 (UTC)

Maintenance catgories

In {{Infobox drug/doc}} I have listed the categories that are mentioned (filled) in the infobox. Some are redlinks. I guess the categorizing logic needs a review. -DePiep (talk) 12:44, 2 January 2015 (UTC)

New Zealand

Hi, I've noticed the drugbox has no legal categorisation for NZ and I'd like to request this change. Fuse809 (talk) 11:21, 7 February 2014 (UTC)

 Done. -DePiep (talk) 07:43, 14 April 2015 (UTC)

The Co-codamol legal_UK field correctly includes both types: POM/P but no link(s) are generated. I manually linked as POM/P. Widefox; talk 01:55, 11 February 2014 (UTC)

Done. Now it links, and the page has been edited. Improved link and text suggestions are welcome, it's a bit code now. (new thread below please). -DePiep (talk) 07:45, 14 April 2015 (UTC)

Protected edit request on 20 Aug 2014: Use protocol relative URL

Since pubchem.ncbi.nlm.nih.gov website supports HTTPS, I suggest switching the link to protocol-relative URL (reason). Here is the change. Thanks! Chmarkine (talk) 19:23, 20 August 2014 (UTC)

Done --Redrose64 (talk) 21:22, 20 August 2014 (UTC)
@Redrose64: Thank you! I just found another link (https://www.nlm.nih.gov/) that can be updated to protocol relatve. Could you apply this change? Thanks! Chmarkine (talk) 00:28, 21 August 2014 (UTC)
 Done – and curious as to why the sandbox is not synched with the live version? – Paine Ellsworth CLIMAX! 07:26, 21 August 2014 (UTC)
Not sure either why the sandbox was not synched. It is now. Boghog (talk) 07:47, 31 August 2014 (UTC)
Possibly a past rendition of the template before it was converted to an Ibox, and just like I still sometimes like to work in DOS, some people are more comfortable with making changes to the previous form, I suppose. Joys! – Paine  22:18, 1 September 2014 (UTC)

Download All Drugboxes?

Anyone know of a way to download all the drugboxes out there for analysis? I'm a researcher interested in analyzing this data. Dalek2point3 (talk) 20:00, 24 September 2014 (UTC)

I guess that would be a task for Wikipedia:Bot requests. Tell them what exactly you want to download – the wikicode, a CSV containing all the fields...? --ἀνυπόδητος (talk) 17:09, 25 September 2014 (UTC)

Rivaroxaban

I can't work out why the image on rivaroxaban is not displaying properly! JFW | T@lk 20:49, 3 September 2014 (UTC)

@Jfdwolff: See Wikipedia:Village pump (technical)/Archive 130#Something is wrong with Wikimedia Commons and the images. --Redrose64 (talk) 21:19, 3 September 2014 (UTC)
@Redrose64: Thanks! JFW | T@lk 22:30, 6 September 2014 (UTC)

3D models

Two things spawned from some comments at Talk:Tetracycline#Cartoon moved here and structure swapped. First, is there any standard for or against including animated 3D diagrams? Given the strong positions of the editor making them and others, I'd like to see some consensus (or at least note of the lack thereof) centralized. Second, what are editors' feelings regarding including an external link to a Jmol model, such as happens automatically (based on the SMILES field) in {{chembox}}? DMacks (talk) 00:05, 2 July 2014 (UTC)

  • For the record, I oppose animated diagrams as distracting, not highly useful, and of often dubious conformational provenance (or worse, likely non-correct due to faulty/non-literature assumptions), and support Jmol links instead as less distracting and more useful. DMacks (talk) 00:11, 2 July 2014 (UTC)
I support the Jmol links but I don't see anything harmful about 3D animated images. If you find something wrong with them, tell me and I will fix them accordingly. Brenton (talk|email) (I automatically watch all pages I edit) 00:55, 2 July 2014 (UTC)
  • oppose animated diagrams – distracting, support jmol links – why not? Concerning the displayed 3D conformation, if it is claimed it is the low energy conformation, or the biologically active conformation, or other similar claim, then it needs a source to support that statement. Otherwise if it is an arbitrarily chosen conformation that makes no claim to relevance of the conformation, then a source is not required. Boghog (talk) 11:24, 2 July 2014 (UTC)
  • Oppose animated diagrams - indeed distracting and often unrealistic (even for non-animated ones; n-hexane would probably have the stretched conformer as the minimum .. sure). Jmol has the same problem in a way, but there we are not claiming that the linear n-hexane is the right conformer. --Dirk Beetstra T C 11:38, 2 July 2014 (UTC)

~~ Copy-pasting someone else's viewpoint (from WT:MEDMOS) that I think is a revelation in this case as it made me change my mind! ~~ Brenton (contribs · email · talk · uploads) 18:46, 23 July 2014 (UTC)

  • Greetings. I'm not a member of this group but I've noticed an issue that I think this group should be aware of. Many of the articles about drugs violate Wikipedia style guidelines. Specifically they have gifs of the drug molecule that rotate and never stop. The latest one I just noticed is: Gabapentin For some people with disabilities (I personally know someone with epilepsy that this is true for) web design like this makes it virtually impossible for them to read the article. I don't have that problem but I do find the gifs extremely annoying. But this isn't about personal preference it's about violating Wikipedia accesibility standards. Here is the relevant policy: Wikipedia:Manual_of_Style_(accessibility)#Animations.2C_videos_and_audio "To be accessible, an animation (GIF – Graphics Interchange Format) should either: not exceed a duration of five seconds (which results in making it a purely decorative element),[6] or be equipped with control functions (stop, pause, play).[7]" I.e., either spin for 5 seconds or less than stop or provide a control so that users can stop the spinning if they want to. A while back I raised this issue on the talk page for Wellbutrin and it was eventually changed but I've noticed it on almost every other drug article that I've visited and don't have the energy to raise it on every talk page. BTW, I would make the change myself, I even looked at the code for the Wellbutrin article but I couldn't figure it out, I've done a lot of editing but I like to write not mess with graphics. IMO, this is fairly important. I would bet money that you are turning off a non-trivial number of users who come to those pages due to the inaccessible design. --MadScientistX11 (talk) 16:16, 23 July 2014 (UTC)

onset field

Please add ONSET field to Pharmacokinetics. Please make it easy and obvious for non-experts to add such appropriate fields one-time ad hoc. (These templates feel very rigid and unfriendly to unexpert editors, quite un-WPish.) -71.174.175.228 (talk) 14:14, 4 August 2014 (UTC)

Since {{infobox}} syntax in general is very complicated and the fact that {{infobox drug}} has been transcluded into a large number of articles, this template has been intentionally edit protected. While the onset of action is determined in part by pharmacokinetics (what the body does to the drug), it is by definition a pharmacodynamic effect (what the drug does to the body). Hence it probably should be listed under pharmacodynamics. On the other hand, we do not have a pharmacodynamics section in the infobox, so I guess it would have to be listed under pharmacokinetics. I have added a new "onset" parameter to the template sandbox and added a test case (see right hand side). Does this look OK? Boghog (talk) 17:22, 4 August 2014 (UTC)
Boghog: Thank you for your prompt and helpful response!!! Without pondering "pharmacokinetics" vs. "pharmacodynamics" as terms/categories -- I only note that my sample source (for Ibuprofen - web.squ.edu.om/med-lib/med_cd/e_cds/Nursing%20Drug%20Guide/mg/ibuprofen.htm) which looked pretty respectable groups all these parameters under "pharmacokinetics". Your test case addition to the template looks good, except that I would suggest that onset logically belongs inserted before half-life.
I have no current reason to want to hack the template; protecting it from non-expert editing seems appropriate (I shudder to imagine the potential immense mess of rippling repercussions from a small subtle error). My issue is with the rigid&frustrating way all the templates seem to function: ad hoc attempts to add misc info in a specific article usually results in no change in the displayed article! This seems against the general spirit of WP. I can usually find some trick to get around this, but only because I am quite stubborn and good at such trickery; the experience always leaves me feeling resentful, and often thinking I should have just given up before investing the time/effort (not to mention queasy that someone will be offended by the hack). I assume that this is a meta-issue in the context of this talk page, and that this is not really an appropriate place for this broad complaint. Since I have avoided exploring the mechanics of templates any more than absolutely necessary, I have no idea where would be the appropriate forum... (Also, this behavior is somewhat inconsistent. While templates are executed so rigidly that "extraneous" well-intentioned content additions often yield no visible results, there remain major vulnerabilities in many other formatting basics. For example, I recently encountered a talk page where a very simple case of mis-matched entry of open and closing grammer on a construct (I think it was a fairly simple ref) in some previous section caused all further material added to the talk page to disappear from view -- not just in that section; any newly added subsequent sections simply vanished from the display. That would be a case where more enforcement and intelligent auto-recovery of page formatting is sorely needed.) -71.174.175.228 (talk) 22:09, 4 August 2014 (UTC)
While the live template is edit protected, the sandboxed version is not. Please feel to experiment with the sandbox if you like. If you would like to request a change to an edit protected template, please place the {{edit template-protected}} with appropriate parameters on the talk page of the template. Per your request, I have moved the onset parameter before half life in the sandbox. This onset parameter is more complicated than I thought because the formulation can strongly affect the time. Per WP:MEDMOS, recent secondary sources (review articles) are strongly preferred. It looks like PMID 20925647 would be a good source to document the onset of action of ibuprofen. Unfortunately the source is behind a paywall, so I do not know the details of what it says about the onset of action of ibuprofen. If everything looks OK and no one else objects, I can add this new parameter to the live version of the template. Boghog (talk) 15:54, 5 August 2014 (UTC)
 Done The onset parameter is now added to the production version of this infobox. Boghog (talk) 07:45, 31 August 2014 (UTC)

Automatic categorization problem

I noticed recently a number of pages appeared in Category:Drug_pages_needing_a_structure_drawing even though they contain images. It appears related to a switch from using the "image = " field to using "imageL =" and "imageR = ". See for example, this edit. Anyone know how to fix this? -- Ed (Edgar181) 13:14, 23 October 2014 (UTC)

Basically, change line 558,
-->{{main other|{{#if:{{{image|}}}{{{image2|}}}
to
-->{{main other|{{#if:{{{image|}}}{{{image2|}}}{{{imageL|}}}{{{imageR|}}}
I hesitate to do this because the code also contains an image3 and an image4 parameter, and I don't really understand how they all are interrelated. --ἀνυπόδητος (talk) 18:20, 23 October 2014 (UTC)
fixed, the image3 and image4 are parameters in {{infobox}}, not in this template :). Frietjes (talk) 19:32, 23 October 2014 (UTC)

They moved the root from

http://www.iuphar-db.org/DATABASE/LigandDisplayForward?ligandId=
to
http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=

Just substitute that line and it will work correctly. Seppi333 (Insert 2¢ | Maintained) 02:08, 8 November 2014 (UTC)

PEL and REL in Chembox

{{Chembox}} already has permissible exposure limit aka PEL (a US legal limit). There is a proposal to add recommended exposure limit aka REL (US, non-legal). Any thoughts on adding both to this Drugbox? See current talk at WT:Chembox, REL. -DePiep (talk) 09:01, 30 January 2015 (UTC)

This would be really nice to have in drugbox because those involved in manufacturing drugs are often exposed to them via different routes (for example, respiration). Emily Temple-Wood (NIOSH) (talk) 04:12, 10 February 2015 (UTC)
I'd like to read more about hazards we want/don't want in the infobox. There are dozens (see {{Chembox}}), so we might need a criteria. -DePiep (talk) 10:22, 20 February 2015 (UTC)
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