Zeranol
      Zeranol|  | 
| Clinical data | 
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| Routes of administration
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| Identifiers | 
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(3S,7R)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
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| Synonyms | α-Zearalanol; Zearalanol; MK-188; P-1496 | 
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| CAS Number | 26538-44-3  N | 
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| PubChem (CID) | 2999413 | 
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| ChemSpider | 2271133  N | 
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| UNII | 76LO2L2V39  Y | 
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| ChEMBL | CHEMBL371463  Y | 
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| ECHA InfoCard | 100.043.411 | 
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| Chemical and physical data | 
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| Formula | C18H26O5 | 
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| Molar mass | 322.40 g·mol−1 | 
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| 3D model (Jmol) | Interactive image | 
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C[C@H]1CCC[C@@H](CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
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InChI=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  NKey:DWTTZBARDOXEAM-GXTWGEPZSA-N  N
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|  N  Y (what is this?)  (verify) | 
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Zeranol (INN, USAN, BAN) (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 naturally occurring mycoestrogen found in fungi in the Fusarium genus and a non-steroidal estrogen used mainly as an anabolic agent in veterinary medicine.[1][2][3]
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.[4] In Canada, it is approved for use in beef cattle only.[5] Its application is not approved for use in the European Union. However, it is marketed under the brand name Ralone in Spain.[2]
Although zeranol may increase cancer cell proliferation in already existing breast cancer,[6] dietary exposure from the use of zeranol-containing implants in cattle is insignificant.[7] 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.[8]
See also
References
- ↑  J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 350–. ISBN 978-1-4757-2085-3. 
- 1 2  Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1105–. ISBN 978-3-88763-075-1. 
- ↑  I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 295–. ISBN 978-94-011-4439-1. 
- ↑  Nichols, Wade; Hutcheson, John; Streeter, Marshall; Corrigan, Mark; Nuttelman, Brandon. "Implant Strategies for Finishing Cattle using Revalor® (trenbolone acetate and estradiol), Finaplix® (trenbolone) and/or Ralgro® (zeranol)" (PDF). Merck Animal Health. 
- ↑  Health Canada, Questions and Answers - Hormonal Growth Promoters
- ↑  Xu, Pingping; Ye, Weiping; Jen, Robert; Lin, Shu-Hong; Kuo, Chieh-Ti; Lin, Young C. (2009-11-01). "Mitogenic activity of zeranol in human breast cancer cells is enhanced by leptin and suppressed by gossypol". Anticancer Research. 29 (11): 4621–4628. ISSN 1791-7530. PMID 20032412. 
- ↑  Lindsay DG (August 1985). "Zeranol--a 'nature-identical' oestrogen?". Food Chem Toxicol. 23 (8): 767–74. PMID 2931335. 
- ↑  Mirocha, CJ; Schauerhamer, B; Christensen, CM; Niku-Paavola, ML; Nummi, M (1979). "Incidence of zearalenol (Fusarium mycotoxin) in animal feed". Applied and Environmental Microbiology. 38 (4): 749–50. PMC 243572 . PMID 161492. . PMID 161492.
 
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| ER | | Agonists | 
 Steroidal: 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol
 DHEA DHEA-S Digitoxin (digitalis) Diosgenin Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin Estetrol Estradiol
 Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol
 Estrofurate Estromustine Estrone
 Etamestrol (eptamestrol) Ethinyl estradiol
 Ethinyl estriol Etynodiol diacetate Guggulsterone Hexolame Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prodiame Prolame Promestriene Quinestradol Quinestrol
  Non-steroidal: (R,R)-THC (S,S)-THC 1-Keto-1,2,3,4-tetrahydrophenanthrene 2,8-DHHHC Allenoic acid Alternariol Anethole Anol Benzestrol Bifluranol Biochanin A Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol
 Diethylstilbestrol
 Dimestrol (dianisylhexene) Dimethylallenolic acid Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Endosulfan ERB-196 (WAY-202196) Estrobin (DBE) Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol
 ICI-85966 (Stilbostat) Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestilbol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methoxychlor Miroestrol Nyasol (cis-hinokiresinol) Paroxypropione Pentafluranol Phenestrol Photoanethole Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Quadrosilan SC-4289 SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Terfluranol WAY-166818 WAY-200070 Triphenylchlorethylene Triphenylmethylethylene WAY-214156
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| See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators |