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

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 470635756

| IUPAC_name = (3''S'',7''R'')-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1''H''-2-benzoxacyclotetradecin-1-one

| image = Alpha Zearalanol.svg

| width = 225px

<!--Clinical data-->

| tradename = Frideron, Ralabol, Ralgro, Ralone, Zerano

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->

| legal_CA =

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

| class = [[Nonsteroidal estrogen]]

<!--Pharmacokinetic data-->

| bioavailability =

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<!-- Identifiers -->

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 26538-44-3

| CAS_supplemental =

| ATCvet =

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem = 2999413

| IUPHAR_ligand =

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 2271133

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

| synonyms = Zearanol; α-Zearalanol; Zearalanol; MK-188; P-1496

<!--Chemical data-->

| C=18 | H=26 | O=5

| SMILES = C[C@H]1CCC[C@H](O)CCCCCc2cc(O)cc(O)c2C(=O)O1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DWTTZBARDOXEAM-GXTWGEPZSA-N

'''Zeranol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) (brand names '''Frideron''', '''Ralabol''', '''Ralgro''', '''Ralone''', '''Zerano'''; developmental code names '''MK-188''', '''P-1496'''), or '''zearanol''', also known as '''α-zearalanol''' or simply '''zearalanol''', is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] of the [[resorcylic acid lactone]] group related to [[mycoestrogen]]s found in [[fungi]] in the ''[[Fusarium]]'' [[genus]] and is used mainly as an [[anabolic]] [[drug|agent]] in [[veterinary medicine]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA350|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=350–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1105|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1105–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA295|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=295–}}</ref>

Zeranol is approved for use as a growth promoter in livestock, including beef cattle, under the brand name '''Ralgro''' (by [[Merck Animal Health]]) in the [[United States]].<ref>{{cite web | title = Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol) | vauthors = Nichols W, Hutcheson J, Streeter M, Corrigan M, Nuttelman B | url = http://www.depts.ttu.edu/afs/implantdb/dbhome/Revalor%20Tech%20Bulletin%2012.pdf }}</ref> In [[Canada]], it is approved for use in beef cattle only.<ref>Health Canada, [http://www.hc-sc.gc.ca/dhp-mps/vet/faq/growth_hormones_promoters_croissance_hormonaux_stimulateurs-eng.php Questions and Answers - Hormonal Growth Promoters]</ref> Its application is not approved for use in the [[European Union]]. However, it is marketed under the brand name '''Ralone''' in [[Spain]].<ref name="IndexNominum2000" />

Although zeranol may increase cancer cell proliferation in already existing [[breast cancer]],<ref>{{cite journal | vauthors = Xu P, Ye W, Jen R, Lin SH, Kuo CT, Lin YC | title = Mitogenic activity of zeranol in human breast cancer cells is enhanced by leptin and suppressed by gossypol | journal = Anticancer Research | volume = 29 | issue = 11 | pages = 4621–4628 | date = November 2009 | pmid = 20032412 }}</ref> dietary exposure from the use of zeranol-containing implants in cattle is insignificant.<ref>{{cite journal | vauthors = Lindsay DG | title = Zeranol--a 'nature-identical' oestrogen? | journal = Food and Chemical Toxicology | volume = 23 | issue = 8 | pages = 767–774 | date = August 1985 | pmid = 2931335 | doi = 10.1016/0278-6915(85)90273-x }}</ref> Zeranol may be found as a contaminant in fungus-infected crops. It is 3 to 4 times more potent as an estrogen than the related compound [[zearalenone]].<ref>{{cite journal | vauthors = Mirocha CJ, Schauerhamer B, Christensen CM, Niku-Paavola ML, Nummi M | title = Incidence of zearalenol (Fusarium mycotoxin) in animal feed | journal = Applied and Environmental Microbiology | volume = 38 | issue = 4 | pages = 749–750 | date = October 1979 | pmid = 161492 | pmc = 243572 | doi = 10.1128/AEM.38.4.749-750.1979 | bibcode = 1979ApEnM..38..749M }}</ref> It is a metabolite of zearalenone.<ref>{{cite journal | vauthors = Miles CO, Erasmuson AF, Wilkins AL, Towers NR, Smith BL, Garthwaite I, Scahill BG, Hansen RP | display-authors = 6 | title = Ovine metabolism of zearalenone to α-zearalanol (zeranol). | journal = Journal of Agricultural and Food Chemistry | date = October 1996 | volume = 44 | issue = 10 | pages = 3244–3250 | doi = 10.1021/jf9601325 }}</ref>

== See also ==

* [[α-Zearalenol]]

* [[β-Zearalenol]]

* [[Taleranol]]

* [[Zearalanone]]

* [[Beef hormone controversy]]

== References ==

{{Reflist}}

{{Toxins}}

{{Xenoestrogens}}

{{Estrogen receptor modulators}}

{{Xenobiotic-sensing receptor modulators}}

[[Category:Lactones]]

[[Category:Mycoestrogens]]

[[Category:Mycotoxins]]

[[Category:Resorcinols]]

[[Category:Veterinary drugs]]

[[Category:World Anti-Doping Agency prohibited substances]]