Talk:Tetracycline

Origin of name

Chemical structure of tetracycline. The name is obviously derived from the structure of the molecule.

Oh, well, obviously. I mean, duh, this is so self-explanatory I don't know why it's even on the page. What, do we have to spell it out for people? Garrett Albright 04:39, 8 Mar 2005 (UTC)

Umm I'm not so sure I should change this page, given my lack of knowledge, but this page is meant to be on the tetracyclic antidepressant group, NOT the antibiotic tetracycline who's name is clocely related. Totally different.

Tetracyclines now redirect to Tetracycline antibiotics that discusses the group in general. This leaves Tetracycline to consider this specific member of the group. David Ruben ^Talk 01:36, 20 February 2006 (UTC)

pKa query

sorry does anyone know the pka of this molecule and whether it is an acid or a base? Posted 01:26, 15 March 2006 by 84.9.116.2

yes the pka is 390 and it is a base pH12 —Preceding unsigned comment added by 78.148.50.47 (talk) 18:30, 28 January 2008 (UTC)

SORRY NONSENSICAL; STILL UNANSWERED. Le Prof Leprof 7272 (talk) 17:11, 1 July 2014 (UTC)

Tetracycline pKa values: pKa1 = 3.3, pKa2 = 7.7, pKa3 = 9.7 (citing A. Martin, 1993, Physical Pharmacy, 4th ed., Lea & Febiger, Philadelphia, page unknown). Note, not confirmed at source, so do not use without verification. Le Prof Leprof 7272 (talk) 17:11, 1 July 2014 (UTC)

invalid link to uspto.gov

The link to uspto.gov leads to 'MACHINE FOR CLEANING OIL COOLER RADIATORS, ETC'; which has nothing to do with tetracycline 69.95.236.244 (talk) 02:25, 7 March 2008 (UTC)

Thank you. Fixed. You still won't be able to read the patent at the USPTO, because it's too old to be stored in text form; but the PDF link will work. TJRC (talk) 02:32, 7 March 2008 (UTC)

things i want to know about the drug

Please,can this drug be use for the cure gonorrhea infection? —Preceding unsigned comment added by 41.210.24.80 (talk) 16:43, 12 July 2009 (UTC)

The brand name Terramycin (instead of tetracycline) was long ago used in STD cases. Don't know if the article should specify which names doctors preferred for treating different types of problems for which tetracycline was effective. This is affected by drug companies using promotional enticements (to doctors) for prescribing certain brand names of tetracycline for treatment. One of my dermatologists earned a trip to Hawaii for prescribing a large number of a specific brand of botox.AnimeJanai (talk) 02:55, 26 June 2011 (UTC)

Don't know, but it can be used for indefinite lengths on the things it does work for and in people who don't have allergic reactions. The -cillins and mycins tend to be used most for STD bacterial infections. The cyclines prescribed seem often prescribed for lysteria or acne. Maybe someone else can answer that? I'm worried about hearing loss if I go on it. Looking for info. -Reticuli 66.178.144.102 (talk) 21:14, 23 April 2011 (UTC)

"Minocycline is the only member in this class that can cause ototoxicity, used mainly for sexually transmitted diseases such as syphilis and gonorrhea. The ototoxic effect is transient. Signs & symptoms occur early, after one or two doses, and are gone one or two days after stopping the medication." http://www.wong.ro/oto/shingvl.html Looks like that answers both of our questions. -Reticuli 66.178.144.102 (talk) 22:20, 23 April 2011 (UTC)

This drug is also used as routine in animal feed. Is this worth a mention? The use is not for disease preventing but many sources use the term "growth promotion" simply stating a higher yield, more efficiency. I would like to know the reasons and mechanisms of this 'growth', whether its effect is same on humans, whether they simply mean more disease resistance, hormonal increases, digestive system effects? — Preceding unsigned comment added by 146.90.201.168 (talk) 23:41, 25 May 2015 (UTC)

Aquarium Usage

Tetracycline has long been used to treat bacterial infections in fish tanks. I think it's safe to say that it's been largely replaced by kanamycin as the front-line, broad-spectrum antibiotic - probably due to the fact that it's much easier to kill fish with tetracycline - but it still sees use by people who know it well, and by people with problems that kanamycin won't solve. I keep fish myself, and I'm treating a tank with tetracycline now. I'm not familiar with any good sources that specifically mention tetracycline, but if anyone else is, I think its use on fish and some information about the procedure would merit inclusion in the article. Stagyar Zil Doggo (talk) 22:27, 26 April 2010 (UTC)

Toxic when expired

I remember reading that Tetracycline is fairly unique among medicines in that it actually becomes toxic (rather than simply less effective) if used after its expiration date. Should be useful to add to the article. (a quick google search shows this may actually be a contested claim as well, and that it may not be harmful to the kidneys) Scott Ritchie (talk) 13:20, 9 August 2010 (UTC)

IUPAC Name

Some of the IUPAC names listened cannot be true. The stereocenters have to be listened in the name. So the name: (4S,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide could be the only right one. If you confirm, delete the other ones listened. Personally I prefer the one listened on German page: (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carbamide Qusai80 (talk) 06:54, 9 May 2011 (UTC)

How Beer Saved The World

Armelagos (Egyptologist) found traces of tetracycline (in mummified bone) almost 3000 years prior to Alexander Fleming's discovery of Penicillin.

The statement, as appearing, is immaterial, even silly. One is about a human discovery of the beta lactam class of natural product antibacterials that transformed man's ability to survive bacterial infections that had theretofore been fatal. The other is about the trace presence of a natural product in an archeological sample (no discovery, and nothing societally transforming). We can identify deuterium in astronomical sources that are older by ridiculous orders of magnitude than the discovery and isolation of the isotope in the last century. So what? What does the existence of an isotope, element, molecule at a stray point of time and space have to do with anything, including its later scientific discovery leading to practical uses? (To be comparably inane, I should have switched from deuterium to carbon-14 during the course of the argument, to parallel Tet vs Pen departure.) Think mon! 'at is nay a hat holder on ye shoulders. Finally, the discovery in mummified bone is as yet pop science, for it remains to be verified and replicated, and so its real significance remains to be seen. The significance of Fleming discovery is clear. Sigh. With the web, the world is now our classroom, and so minds are spread more thinly over larger territories than ever before. Le Prof Leprof 7272 (talk) 17:11, 1 July 2014 (UTC)

Mechanism of action

The mechanism of action section states "Mammalian cells are less vulnerable to the effect of tetracyclines, as these contain no 30S ribosomal subunits." Is this statement correct? What about the ribosomes of mitochondria that are contained within mammalian cells? I am under the impression that large doses of medications that inhibit bacterial protein synthesis can prove toxic for mammals, as mitochondrial protein synthesis could be disrupted. References: (1.) Discovery Channel Documentary, How Beer Saved The World min15., (2.) http://www.sciencedaily.com/releases/2010/09/100902094246.htm, (3.) http://www.livescience.com/11028-ancient-african-cocktail-beer-shot-antibiotic.html — Preceding unsigned comment added by Avkrules (talk • contribs) 20:48, 20 December 2011 (UTC)

Very valid point, bravo/brava!. However, none of these are valid Wikipedia sources, which require solid secondary sources for scientific content. These are news reports and pop science (which are based on university press releases and the perspective of popularizers, and so may or may not reflect a preponderance of scientific opinion). Find the scholarly reviews or book chapters, or leave out until found. Le Prof Leprof 7272 (talk) 17:11, 1 July 2014 (UTC)

Cartoon moved here and structure swapped

First, the static 2D structure that appeared in the infobox in the article, here, earlier, represented the title molecule's stereochemistry within rings and at ring junctures incorrectly. I therefore swapped it for one that was a standard, accurate representation. This image of the molecule is flipped and rotated (relative to how it appeared before), but it is identical, exceot for its accurate representation of stereochemistry at ring junctures. If one can find a better image than this, fine, but (i) under no circumstances return Tetracycline2DCSD.svg, which I am annotating as unusable at Wikimedia; (2) note that many tetracycline structures at the Commons have the tertiary alcohol locus represented by two R groups, and these images can only be used with a carefully constructed, accurate legend, and (3) there is a bias among most of the best OChemists to show terminal methyl groups and hydrogens at stereocenters in their structural representations, and I follow these conventions in creating or choosing images. This chosen image is not perfect, but it is accurate, and "conventional".

Second, I strenuously object, as a subject matter expert, to use of animations that are not tied to the text to make a point, and so have no basis in scientific presentation. We are not idiots, needing to be entertained, nor are our readers. If there is a point to cartoon, add it to the article, clearly, and with citation, and then re-add this animation file to the article. But if there is no point, there is no point, and it is a misrepresentation of science. If you care about rigour, read on. Here is the moved cartoon:

3D representations of molecules are only rigourous, and so meaningful, if they include details in the legend as to how they were derived. If the cartoon of the molecule shown in the infobox is a representative of an ensemble of low energy structures derived by MM2 or MD computations, say so, and give some detail (summarizing more complete information on the image page at Wikimidia Commons). And then, as I said, complete the legend by saying why the cartoon with its sampling of poses, was chosen and is presented. A computed structure, if well done and annotated, is WP:OR at best, and at worst is simply nonsense. Make clear that the 3D images you post are not nonsense; see [1] and [2] by way of example. Note, our inorganic colleagues tend to do this, widely, in their images; we organic chemists seem to forget that when we move from 2D to 3D it must involve science.

Le Prof Leprof 7272 (talk) 17:11, 1 July 2014 (UTC)

I have long been troubled by these 3D animations, both in terms of their chemical accuracy and usefulness to readers. "Chemical" infoboxes have automatic links to JMol rendering, allowing the reader to manipulate a 3D model as desired. They are stereochemically correct but not conformationally minimized for the exact structure, so it allows the reader to get a good sense of a "reasonable and approximate" way of seeing many of the geometric details. "Drug" infoboxes do not appear to have this feature, but it sounds like a chance to push for a single-point fix that would improve many articles. On the other hand, these JMol fail badly for many inorganics and other ionic clusters having many ligands...that's on my list of things to work on...some day. DMacks (talk) 23:51, 1 July 2014 (UTC)

I have started Template talk:Infobox drug#3D models. Feel free to continue discussing there that general aspect of drugboxes. DMacks (talk) 00:05, 2 July 2014 (UTC)

I hate these animations, which I find distracting and annoying. About energy minimization, I dont really care so much so long as the conformations are roughly ok. Most of these images seem to be uploaded by newish editors who, for the best of instincts, are super-keen to contribute to Wikipedia-Chem, but dont know enough to write anything meaningful, so they use their computer skills to make nifty images. --Smokefoot (talk) 12:58, 2 July 2014 (UTC)

3D yes, 3D animation no. • Sbmeirow • Talk • 19:38, 23 December 2023 (UTC)

Sentence moved to Talk as likely unrelated to article

For an expert's attention and decision: The following sentence is moved here, with its citatiion, because it appears to related solely to another member of the tetracycline class, and not to tetracycline per se:

According to the U.S. FDA, there are case reports of Stevens–Johnson syndrome, toxic epidermal necrolysis and erythema multiforme associated with doxycyline use but a causative role has not been established.

If it should, for any reason, belong in this article, feel free to return it to an apporpriate place. Cheers. Le Prof 73.210.155.96 (talk) 15:37, 13 March 2017 (UTC)

That editor apparently somehow came to think that they were editing an article on the tetracycline class of antibiotics.--Quisqualis (talk) 05:41, 14 March 2017 (UTC)

Have reverted back. This article is about a single antibiotic not the tetracycline antibiotics class which we linked in the first sentence. Doc James (talk · contribs · email) 19:35, 14 March 2017 (UTC)

Medical uses

In the introduction it is written that tetracycline is used to treat bacterial infections such as Malaria. Malaria is protozoal not bacterial - perhaps this should be made clearer? 80.227.64.188 (talk) 05:56, 21 March 2017 (UTC)

i fixed the lead. the body was correct already - it noted "These agents also have activity against certain eukaryotic parasites, including those responsible for diseases such as malaria and balantidiasis."

Not only by mouth

See https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0012373/ ---- Jidanni (talk) 09:29, 12 October 2017 (UTC)