Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tetracycline: Difference between pages

{{Short description|Antibiotic used to treat a number of infections}}

{{About|the specific antibiotic|the family of antibiotics|Tetracycline antibiotics}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 470603713

| drug_name =

| image = [[File:Tetracycline skeletal.svg|frameless|tetracycline 2D skeletal]]

| image2 = [[File:Tetracycline.png|frameless|tetracycline 3D BS]]

| synonyms = TE/TET/TC/TCY<ref>{{cite web |title=Antibiotic abbreviations list |url=https://microbiologie-clinique.com/antibiotic-family-abbreviation.html |access-date=22 June 2023}}</ref>

| pronounce = {{IPAc-en|ˌ|t|ɛ|t|r|ə|ˈ|s|aɪ|k|l|iː|n}}

| tradename =

| Drugs.com = {{drugs.com|monograph|tetracycline}}

| MedlinePlus = a682098

| licence_US = Tetracycline

| pregnancy_AU = D

| pregnancy_US = D

| legal_status = Rx-only

| routes_of_administration = [[Oral administration|By mouth]]

| bioavailability = 80%

| metabolism = Not metabolized

| elimination_half-life = 8–11 hours, 57–108 hours (kidney impairment)

| excretion = Urine (>60%), feces

| IUPAC_name = (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide<ref>{{Cite PubChem|cid=54675776}}</ref>

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 60-54-8

| CAS_supplemental = <br>{{CAS|64-75-5}} (hydrochloride) <!-- Also CAS verified -->

| ATC_prefix = A01

| ATC_suffix = AB13

| ATC_supplemental = {{ATC|D06|AA04}} {{ATC|J01|AA07}} {{ATC|S01|AA09}} {{ATC|S02|AA08}} {{ATC|S03|AA02}} {{ATCvet|G01|AA90}} {{ATCvet|G51|AA02}} {{ATCvet|J51|AA07}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 27902

| PubChem = 54675776

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00759

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10257122

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = F8VB5M810T

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00201

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1440

| PDB_ligand = TAC

<!--Chemical data-->| C = 22

| H = 24

| N = 2

| O = 8

| smiles = C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OFVLGDICTFRJMM-WESIUVDSSA-N

<!-- Definition and medical uses -->

'''Tetracycline''', sold under various brand names, is an oral [[antibiotic]] in the [[tetracyclines]] family of medications, used to treat a number of [[infections]],<ref name=AHFS2016/> including [[Acne vulgaris|acne]], [[cholera]], [[brucellosis]], [[plague (disease)|plague]], [[malaria]], and [[syphilis]].<ref name=AHFS2016/>

<!-- Side effects and mechanism -->

Common side effects include vomiting, [[diarrhea]], rash, and loss of appetite.<ref name=AHFS2016/> Other side effects include poor [[tooth]] development if used by children less than eight years of age, [[kidney problems]], and [[sunburn]]ing easily.<ref name=AHFS2016/> Use during [[pregnancy]] may harm the baby.<ref name=AHFS2016/> It works by inhibiting protein synthesis in bacteria.<ref name=AHFS2016>{{cite web|title=Tetracycline|url=https://www.drugs.com/monograph/tetracycline.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161228195613/https://www.drugs.com/monograph/tetracycline.html|archive-date=28 December 2016}}</ref>

<!-- Society and culture -->

Tetracycline was patented in 1953<ref>{{US patent|2699054A}}</ref> and was approved for prescription use in 1954.<ref name=History/><ref>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=489|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA489|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220084414/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA489|archive-date=2016-12-20}}</ref> It is on the [[World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO }}</ref> Tetracycline is available as a [[generic medication]].<ref name=AHFS2016/> Tetracycline was originally made from bacteria of the genus ''[[Streptomyces]]''.<ref name=AHFS2016/>

==Medical uses==

=== Spectrum of activity ===

Tetracyclines have a broad spectrum of antibiotic action. Originally, they possessed some level of bacteriostatic activity against almost all medically relevant [[Aerobic bacteria|aerobic]] and [[Anaerobic bacteria|anaerobic]] bacterial genera, both [[Gram-positive bacteria|Gram-positive]] and [[Gram-negative bacteria|Gram-negative]], with a few exceptions, such as ''[[Pseudomonas aeruginosa]]'' and [[Proteus (bacterium)|''Proteus'' spp.]], which display intrinsic resistance. However, acquired (as opposed to inherent) resistance has proliferated in many [[pathogenic organisms]] and greatly eroded the formerly vast versatility of this group of antibiotics. Resistance amongst [[Staphylococcus|''Staphylococcus'' spp.]], [[Streptococcus|''Streptococcus'' spp.]], ''[[Neisseria gonorrhoeae]]'', anaerobes, members of the [[Enterobacteriaceae]], and several other previously sensitive organisms is now quite common. Tetracyclines remain especially useful in the management of infections by certain obligately intracellular bacterial pathogens such as ''[[Chlamydia (genus)|Chlamydia]]'', ''[[Mycoplasma]]'', and ''[[Rickettsia]]''. They are also of value in [[Spirochete|spirochaetal]] infections, such as [[syphilis]], and [[Lyme disease]]. Certain rare or exotic infections, including [[anthrax]], [[Plague (disease)|plague]], and [[brucellosis]], are also susceptible to tetracyclines. Tetracycline tablets were used in the plague outbreak in India in 1994.<ref>Lippincott's Illustrated Reviews: Pharmacology, 4th ed. Harvery RA, Champe, PC. Lippincott, Williams & Wilkins, 2009</ref> Tetracycline is first-line therapy for [[Rocky Mountain spotted fever]] (''Rickettsia''), [[Lyme disease]] (''B. burgdorferi''), [[Q fever]] (''Coxiella''), [[psittacosis]], ''[[Mycoplasma pneumoniae]]'', and nasal carriage of [[Neisseria meningitidis|meningococci]].{{cn|date=March 2023}}

It is also one of a group of antibiotics which together may be used to treat [[Peptic ulcer#H. pylori 2|peptic ulcers]] caused by bacterial infections. The mechanism of action for the antibacterial effect of tetracyclines relies on disrupting protein translation in bacteria, thereby damaging the ability of microbes to grow and repair; however, protein translation is also disrupted in eukaryotic [[mitochondria]] leading to effects that may [[confound]] experimental results.<ref name="pmid25772356">{{cite journal | vauthors = Moullan N, Mouchiroud L, Wang X, Ryu D, Williams EG, Mottis A, Jovaisaite V, Frochaux MV, Quiros PM, Deplancke B, Houtkooper RH, Auwerx J | title = Tetracyclines Disturb Mitochondrial Function across Eukaryotic Models: A Call for Caution in Biomedical Research | journal = Cell Reports | volume = 10 | issue = 10 | pages = 1681–1691 | date = March 2015 | pmid = 25772356 | pmc = 4565776 | doi = 10.1016/j.celrep.2015.02.034 }}</ref><ref name="pmid26475870">{{cite journal | vauthors = Chatzispyrou IA, Held NM, Mouchiroud L, Auwerx J, Houtkooper RH | title = Tetracycline antibiotics impair mitochondrial function and its experimental use confounds research | journal = Cancer Research | volume = 75 | issue = 21 | pages = 4446–4449 | date = November 2015 | pmid = 26475870 | pmc = 4631686 | doi = 10.1158/0008-5472.CAN-15-1626 }}</ref>

The following list presents [[Minimum inhibitory concentration|MIC]] susceptibility data for some medically significant microorganisms:

* ''[[Escherichia coli]]:'' 1 {{abbr|μg|microgram}}/{{abbr|mL|mililiter}} to >128 μg/mL

* ''[[Shigella]]'' {{abbr|spp.|subspecies}}: 1 μg/mL to 128 μg/mL<ref>{{cite web | title = Tetracycline hydrochloride | work = Susceptibility and Minimum Inhibitory Concentration (MIC) Data | date = 8 September 2015 | publisher = TOKU-E | url = http://www.toku-e.com/Assets/MIC/Tetracycline%20hydrochloride.pdf | archive-url = https://web.archive.org/web/20150908102809/http://www.toku-e.com/Assets/MIC/Tetracycline%20hydrochloride.pdf | archive-date = 8 September 2015 }}</ref>

===Anti-eukaryote use===

The tetracyclines also have activity against certain [[Eukaryota|eukaryotic]] parasites, including those responsible for diseases such as [[Amoebic dysentery|dysentery]] caused by an [[amoeba]], [[malaria]] (a [[plasmodium]]), and [[balantidiasis]] (a [[ciliate]]).{{cn|date=March 2023}}

===Use as a biomarker===

[[File:Tetracycline-HCl substance photo.jpg|thumb|Tetracycline hydrochloride is available as yellow crystalline powder.]]

Since tetracycline is absorbed into bone, it is used as a marker of bone growth for [[biopsies]] in humans. Tetracycline labeling is used to determine the amount of bone growth within a certain period of time, usually a period around 21 days. Tetracycline is incorporated into mineralizing bone and can be detected by its [[fluorescence]].<ref name=mayton>{{cite web | vauthors = Mayton CA | url = http://www.histosearch.com/histonet/Dec02/TetracyclinelabelingofbonA.html | title = Tetracycline labeling of bone | archive-url = https://web.archive.org/web/20070312193518/http://www.histosearch.com/histonet/Dec02/TetracyclinelabelingofbonA.html | archive-date=2007-03-12 }}</ref> In "double tetracycline labeling", a second dose is given 11–14 days after the first dose, and the amount of bone formed during that interval can be calculated by measuring the distance between the two fluorescent labels.<ref>{{cite web | url = http://pathology2.jhu.edu/bonelab/4cycline.htm | work = The Johns Hopkins Medical Institutions. | title = Tetracycline Labeling | archive-url = https://archive.today/20121215013608/http://pathology2.jhu.edu/bonelab/4cycline.htm | archive-date=2012-12-15 | date = 8 January 2001 }}</ref>

Tetracycline is also used as a biomarker in [[wildlife]] to detect consumption of medicine- or [[vaccine]]-containing baits.<ref>{{cite journal | vauthors = Olson CA, Mitchell KD, Werner PA | title = Bait ingestion by free-ranging raccoons and nontarget species in an oral rabies vaccine field trial in Florida | journal = Journal of Wildlife Diseases | volume = 36 | issue = 4 | pages = 734–743 | date = October 2000 | pmid = 11085436 | doi = 10.7589/0090-3558-36.4.734 | url = http://www.jwildlifedis.org/cgi/reprint/36/4/734 | url-status = dead | s2cid = 35102508 | archive-url = https://archive.today/20130415041932/http://www.jwildlifedis.org/cgi/reprint/36/4/734 | archive-date = 2013-04-15 }}</ref>

== Side effects ==

{{See also|Tooth bleaching}}

{{more med cn|section|date=November 2022}}

Use of [[tetracycline antibiotics]] can:<ref>{{Cite web|url=https://medlineplus.gov/druginfo/meds/a682098.html|title=Tetracycline: MedlinePlus Drug Information|website=medlineplus.gov|language=en|access-date=2017-05-19|url-status=live|archive-url=https://web.archive.org/web/20170510164238/https://medlineplus.gov/druginfo/meds/a682098.html|archive-date=2017-05-10}}</ref>

* Discolor permanent teeth (yellow-gray-brown), from prenatal period through childhood and adulthood.<ref>{{cite journal | vauthors = Sánchez AR, Rogers RS, Sheridan PJ | title = Tetracycline and other tetracycline-derivative staining of the teeth and oral cavity | journal = International Journal of Dermatology | volume = 43 | issue = 10 | pages = 709–715 | date = October 2004 | pmid = 15485524 | doi = 10.1111/j.1365-4632.2004.02108.x }}</ref><ref name=":0" /> Children receiving long- or short-term therapy with a tetracycline or glycylcycline may develop permanent brown discoloration of the teeth.

* Be inactivated by calcium [[ion]]s, so are not to be taken with [[milk]], [[yogurt]], and other [[dairy product|dairy]] products

* Be inactivated by [[aluminium]], [[iron]], and [[zinc]] ions, not to be taken at the same time as [[indigestion]] remedies (some common antacids and over-the-counter heartburn medicines)

* Cause [[skin]] [[photosensitivity]],<ref name=":0">{{cite book | vauthors = Shutter MC, Akhondi H | chapter = Tetracycline |date=2024 | title = StatPearls | chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK549905/ |access-date=2024-03-19 |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=31751095 }}</ref> so exposure to the [[sun]] or intense [[light]] is not recommended

* Cause drug-induced [[Lupus erythematosus|lupus]], and [[hepatitis]]

* Cause microvesicular [[fatty liver]]<ref>{{Citation |title=Demeclocycline |date=2012 |work=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury |url=http://www.ncbi.nlm.nih.gov/books/NBK548848/ |access-date=2024-03-20 |place=Bethesda (MD) |publisher=National Institute of Diabetes and Digestive and Kidney Diseases |pmid=31644155}}</ref>

* Cause [[tinnitus]]<ref>{{Cite web |date=August 15, 2022 |title=Tinnitus: Ringing in the ears and what to do about it |url=https://www.health.harvard.edu/newsletter_article/tinnitus-ringing-in-the-ears-and-what-to-do-about-it |website=Harvard Health Publishing Harvard Medical School}}</ref><ref>{{Cite book|title=Antibiotics Manual : A Guide to Commonly Used Antimicrobials| vauthors = Schlossberg DL, Samuel R |publisher=John Wiley & Sons, Inc.|year=2017|pages=367|via=ProQuest Ebook Central}}</ref>

* Cause [[epigastric pain]]<ref name=":0" />

* Interfere with [[methotrexate]] by displacing it from the various protein-binding sites

* Cause breathing complications, as well as [[anaphylactic shock]], in some individuals

* Affect bone growth of the [[fetus]], so should be avoided during [[pregnancy]]

* [[Fanconi syndrome]] may result from ingesting expired tetracyclines.

Caution should be exercised in long-term use when breastfeeding. Short-term use is safe; [[bioavailability]] in milk is low to nil.<ref>{{cite book | veditors = Riordan J, Wambach K | title = Breastfeeding and Human Lactation | publisher= Jones & Bartlett Learning | date = November 2010 | page = 179 }}</ref> According to the U.S. [[Food and Drug Administration]] (FDA), cases of [[Stevens–Johnson syndrome]], [[toxic epidermal necrolysis]], and [[erythema multiforme]] associated with [[doxycycline]] use have been reported, but a causative role has not been established.<ref name=AERSlist>{{cite web | url = https://www.fda.gov/Drugs/GuidanceComplianceRegulatoryInformation/Surveillance/AdverseDrugEffects/ucm223734.htm | title = FDA Adverse Events Reporting System | website = [[Food and Drug Administration]] | date = 27 August 2010 | archive-url = https://web.archive.org/web/20110117121827/https://www.fda.gov/Drugs/GuidanceComplianceRegulatoryInformation/Surveillance/AdverseDrugEffects/ucm223734.htm | archive-date=2011-01-17 | access-date = 14 January 2011 }}</ref>

==Pharmacology==

===Mechanism of action===

Tetracycline inhibits protein synthesis by blocking the attachment of charged [[aminoacyl-tRNA|tRNA]] at the [[Ribosome|P site]] peptide chain. Tetracycline blocks the A-site so that a hydrogen bond is not formed between the amino acids. Tetracycline binds to the 30S and 50S subunit of microbial ribosomes.<ref name=AHFS2016/> Thus, it prevents the formation of a peptide chain.<ref>{{cite web | vauthors = Mehta A |url=http://pharmaxchange.info/press/2011/05/mechanism-of-action-of-tetracyclines/ |title=Mechanism of Action of Tetracyclines |publisher=Pharmaxchange.info |date=2011-05-27 |access-date=2012-06-07 |url-status=live |archive-url=https://web.archive.org/web/20120605235017/http://pharmaxchange.info/press/2011/05/mechanism-of-action-of-tetracyclines/ |archive-date=2012-06-05 }}</ref> The action is usually not inhibitory and irreversible even with the withdrawal of the drug. [[Mammal]]ian cells are less vulnerable to the effect of tetracyclines, despite the fact that tetracycline binds to the small ribosomal subunit of both [[prokaryotes]] and [[eukaryotes]] (30S and 40S, respectively). This is because bacteria actively pump tetracycline in, even against a concentration gradient{{Dubious|date=November 2023|reason=Seems unlikely, see http://dx.doi.org/10.2174/1874091X01913010001}}, whereas mammalian cells are simply not affected by the mechanisms of tetracycline within the cytoplasm. This accounts for the relatively small off-site effect of tetracycline on human cells.<ref>{{cite book | vauthors = Todar K | chapter = Antimicrobial Agents in the Treatment of Infectious Disease. | title = Todars Online Text Book of Bacteriology | date = 2012 | chapter-url = http://textbookofbacteriology.net/antimicrobial_4.html |access-date=2013-08-27 |url-status=live |archive-url=https://web.archive.org/web/20131008103423/http://textbookofbacteriology.net/antimicrobial_4.html |archive-date=2013-10-08 }}</ref>

===Mechanisms of resistance===

Bacteria usually acquire resistance to tetracycline from [[horizontal gene transfer|horizontal transfer]] of a [[gene]] that either encodes an [[efflux pump]] or a ribosomal protection protein. Efflux pumps actively eject tetracycline from the cell, preventing the build up of an inhibitory concentration of tetracycline in the [[cytoplasm]].<ref>{{cite journal | vauthors = Chopra I, Roberts M | title = Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance | journal = Microbiology and Molecular Biology Reviews | volume = 65 | issue = 2 | pages = 232–60 ; second page, table of contents | date = June 2001 | pmid = 11381101 | pmc = 99026 | doi = 10.1128/MMBR.65.2.232-260.2001 }}</ref> Ribosomal protection proteins interact with the ribosome and dislodge tetracycline from the ribosome, allowing for translation to continue.<ref>{{cite journal | vauthors = Connell SR, Tracz DM, Nierhaus KH, Taylor DE | title = Ribosomal protection proteins and their mechanism of tetracycline resistance | journal = Antimicrobial Agents and Chemotherapy | volume = 47 | issue = 12 | pages = 3675–3681 | date = December 2003 | pmid = 14638464 | pmc = 296194 | doi = 10.1128/AAC.47.12.3675-3681.2003 }}</ref>

== History ==

=== Discovery ===

The tetracyclines, a large family of antibiotics, were discovered by [[Benjamin Minge Duggar]] in 1948 as natural products, and first prescribed in 1948.<ref>{{cite web | vauthors = Klajn R | url = http://www.chm.bris.ac.uk/motm/tetracycline/tetracycline.htm | title = Chemistry and chemical biology of tetracyclines | archive-url = https://web.archive.org/web/20070617003719/http://www.chm.bris.ac.uk/motm/tetracycline/tetracycline.htm | archive-date=2007-06-17 | access-date = 20 June 2007}} {{better source needed|date=March 2017}}</ref> Benjamin Duggar, working under [[Yellapragada Subbarow]] at [[American Cyanamid|Lederle Laboratories]], discovered the first tetracycline antibiotic, [[chlortetracycline]] (Aureomycin), in 1945.<ref>{{cite journal | vauthors = Jukes TH | title = Some historical notes on chlortetracycline | journal = Reviews of Infectious Diseases | volume = 7 | issue = 5 | pages = 702–707 | date = 1985 | pmid = 3903946 | doi = 10.1093/clinids/7.5.702 | jstor = 4453725 }}</ref> The structure of Aureomycin was elucidated in 1952 and published in 1954 by the Pfizer-Woodward group.<ref>{{Cite journal | vauthors = Stephens CR, Conover LH, Pasternack R, Hochstein FA, Moreland WT, Regna PP, Pilgrim FJ, Brunings KJ, Woodward RB |date=July 1954 |title=The Structure of Aureomycin 1 |url=https://pubs.acs.org/doi/abs/10.1021/ja01642a064 |journal=Journal of the American Chemical Society |language=en |volume=76 |issue=13 |pages=3568–3575 |doi=10.1021/ja01642a064 |issn=0002-7863}}</ref> After the discovery of the structure, researchers at [[Pfizer]] began chemically modifying aureomycin by treating it with hydrogen in the presence of a [[Palladium on carbon|palladized carbon catalyst]]. This [[chemical]] reaction replaced a chlorine moiety with a hydrogen, creating a compound named tetracycline via [[hydrogenolysis]].<ref>{{Cite journal | vauthors = Conover LH, Moreland WT, English AR, Stephens CR, Pilgrim FJ |title=Terramycin. Xi. Tetracycline |date=September 1953 |url=https://pubs.acs.org/doi/abs/10.1021/ja01114a537 |journal=Journal of the American Chemical Society |language=en |volume=75 |issue=18 |pages=4622–4623 |doi=10.1021/ja01114a537 |issn=0002-7863}}</ref> Tetracycline displayed higher potency, better solubility, and more favorable pharmacology than the other antibiotics in its class, leading to its FDA approval in 1954. The new compound was one of the first commercially successful semi-synthetic antibiotics that was used, and laid the foundation for the development of Sancycline, [[Minocycline]], and later the [[Glycylcycline]]s.<ref name= History>{{cite journal | vauthors = Nelson ML, Levy SB | title = The history of the tetracyclines | journal = Annals of the New York Academy of Sciences | volume = 1241 | issue = 1 | pages = 17–32 | date = December 2011 | pmid = 22191524 | doi = 10.1111/j.1749-6632.2011.06354.x | bibcode = 2011NYASA1241...17N | s2cid = 34647314 }}</ref>

===Evidence in antiquity===

Tetracycline has a high affinity for calcium and is incorporated into bones during the active mineralization of [[hydroxyapatite]]. When incorporated into bones, tetracycline can be identified using ultraviolet light.<ref>{{cite journal | vauthors = Pautke C, Vogt S, Kreutzer K, Haczek C, Wexel G, Kolk A, Imhoff AB, Zitzelsberger H, Milz S, Tischer T | title = Characterization of eight different tetracyclines: advances in fluorescence bone labeling | journal = Journal of Anatomy | volume = 217 | issue = 1 | pages = 76–82 | date = July 2010 | pmid = 20456523 | pmc = 2913014 | doi = 10.1111/j.1469-7580.2010.01237.x }}</ref>

There is evidence that early inhabitants of Northeastern Africa consumed tetracycline antibiotics. [[Nubian people|Nubian]] mummies from between 350 and 550 A.D. were found to exhibit patterns of fluorescence identical with that of modern tetracycline labelled bone.<ref>{{cite journal | vauthors = Bassett EJ, Keith MS, Armelagos GJ, Martin DL, Villanueva AR | title = Tetracycline-labeled human bone from ancient Sudanese Nubia (A.D. 350) | journal = Science | volume = 209 | issue = 4464 | pages = 1532–1534 | date = September 1980 | pmid = 7001623 | doi = 10.1126/science.7001623 | bibcode = 1980Sci...209.1532B }}</ref>

It is conjectured that the beer brewed by the Nubians was the source of the tetracycline found in these bones.<ref>{{cite journal | vauthors = Armelagos G |date=2000 |title=Take Two Beers and Call Me in 1,600 Years: Use of Tetracycline by Nubians and Ancient Egyptians |journal = Natural History |volume=109 |issue=4 |pages=50–53 }}</ref>

==Society and culture==

===Price===

According to data from EvaluatePharma and published in the ''[[Boston Globe]]'', in the USA the price of tetracycline rose from $0.06 per 250-[[Milligram|mg]] pill in 2013 to $4.06 a pill in 2015.<ref name="bostonglobe_2015_11">{{cite web | url=https://www.bostonglobe.com/business/2015/11/06/generic-drug-price-increases-alarm-insurers-providers-and-consumers/H3iA9CSxAUylnCdGjLNKVN/story.html?event=event25 | title=As competition wanes, prices for generics skyrocket | work=Boston Globe | date=6 November 2015 | access-date=18 November 2015 | vauthors = McCluskey PD | url-status=live | archive-url=https://web.archive.org/web/20151119073901/http://www.bostonglobe.com/business/2015/11/06/generic-drug-price-increases-alarm-insurers-providers-and-consumers/H3iA9CSxAUylnCdGjLNKVN/story.html?event=event25 | archive-date=19 November 2015 }}</ref> The ''Globe'' described the "big price hikes of some generic drugs" as a "relatively new phenomenon" which has left most pharmacists "grappling" with large upswings" in the "costs of generics, with 'overnight' price changes sometimes exceeding 1,000%."<ref name="bostonglobe_2015_11" />

===Names===

It is marketed under the brand names Sumycin, Tetracyn, and Panmycin, among others. Actisite is a thread-like fiber formulation used in dental applications.{{cn|date=March 2023}}

It is also used to produce several semisynthetic derivatives, which together are known as the [[tetracycline antibiotics]]. The term "tetracycline" is also used to denote the four-ring system of this compound; "tetracyclines" are related substances that contain the same four-ring system.{{cn|date=March 2023}}

===Media===

Due to the drug's association with fighting infections, it serves as the main "commodity" in the science fiction series [[Aftermath (2016 TV series)|Aftermath]], with the search for tetracycline becoming a major preoccupation in later episodes.<ref>{{cite web |title=Aftermath Episode Recap |url=https://www.syfy.com/aftermath/episodes/season/2016/episode/9/the-barbarous-king |website=SyFy Channel |access-date=15 April 2020 |archive-date=13 October 2017 |archive-url=https://web.archive.org/web/20171013003356/http://www.syfy.com/aftermath/episodes/season/2016/episode/9/the-barbarous-king |url-status=dead }}</ref>

Tetracycline is also represented in [[Bohemia Interactive]]'s survival sandbox, [[DayZ (video game)|DayZ]]. In the game, players may find the antibiotic to treat the common cold, influenza, cholera and infected wounds, but does not portray any side effects associated with tetracycline.

==Research==

===Genetic engineering===

In [[genetic engineering]], tetracycline is used in [[Tetracycline-controlled transcriptional activation|transcriptional activation]]. It has been used as an engineered "control switch" in [[chronic myelogenous leukemia]] models in mice. Engineers were able to develop a retrovirus that induced a particular type of leukemia in mice, and could then "switch" the cancer on and off through tetracycline administration. This could be used to grow the cancer in mice and then halt it at a particular stage to allow for further experimentation or study.<ref>{{cite journal | vauthors = Dugray A, Geay JF, Foudi A, Bonnet ML, Vainchenker W, Wendling F, Louache F, Turhan AG | title = Rapid generation of a tetracycline-inducible BCR-ABL defective retrovirus using a single autoregulatory retroviral cassette | journal = Leukemia | volume = 15 | issue = 10 | pages = 1658–1662 | date = October 2001 | pmid = 11587226 | doi = 10.1038/sj.leu.2402225 | s2cid = 40155100 | doi-access = }}</ref>

A technique being developed for the control of the [[mosquito]] species ''[[Aedes aegypti]]'' (the infection [[Vector (epidemiology)|vector]] for [[yellow fever]], [[dengue fever]], [[Zika fever]], and several other diseases) uses a strain that is [[genetically modified]] to require tetracycline to develop beyond the larval stage. Modified males raised in a laboratory develop normally as they are supplied with this chemical and can be released into the wild. Their subsequent offspring inherit this trait, but find no tetracycline in their environments, so never develop into adults.<ref>{{cite news| vauthors = Urquhart C | title= Can GM mosquitoes rid the world of a major killer?| newspaper= The Observer| date= 15 July 2012| url= https://www.theguardian.com/environment/2012/jul/15/gm-mosquitoes-dengue-fever-feature| access-date= 2012-07-15| url-status= live| archive-url= https://web.archive.org/web/20131205105805/http://www.theguardian.com/environment/2012/jul/15/gm-mosquitoes-dengue-fever-feature| archive-date= 5 December 2013}}</ref>

== References ==

{{Reflist}}

== External links ==

* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/tetracycline | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Tetracycline }}

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