:Zeranol

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = 470635756

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

| image = Alpha Zearalanol.svg

| width = 225px

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

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| routes_of_administration = By mouth

| class = Nonsteroidal estrogen

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

| CAS_number = 26538-44-3

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| PubChem = 2999413

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

| ChemSpiderID = 2271133

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

| UNII = 76LO2L2V39

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| ChEMBL = 371463

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

| 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

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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 nonsteroidal estrogen of the resorcylic acid lactone group related to mycoestrogens found in fungi in the Fusarium genus and is used mainly as an anabolic agent in veterinary medicine.{{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–}}{{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–}}{{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–}}

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.{{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 }} In Canada, it is approved for use in beef cattle only.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] Its application is not approved for use in the European Union. However, it is marketed under the brand name Ralone in Spain.

Although zeranol may increase cancer cell proliferation in already existing breast cancer,{{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 }} dietary exposure from the use of zeranol-containing implants in cattle is insignificant.{{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 }} 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.{{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 }} It is a metabolite of zearalenone.{{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 | bibcode = 1996JAFC...44.3244M }}