Zeranol

Zeranol

Clinical data
Routes of administration	Oral
Identifiers
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
Synonyms	α-Zearalanol; Zearalanol; MK-188; P-1496
CAS Number	26538-44-3
PubChem (CID)	2999413
ChemSpider	2271133
UNII	76LO2L2V39
ChEMBL	CHEMBL371463
ECHA InfoCard	100.043.411
Chemical and physical data
Formula	C18H26O5
Molar mass	322.40 g·mol^−1
3D model (Jmol)	Interactive image
SMILES C[C@H]1CCC[C@@H](CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
InChI 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 Key:DWTTZBARDOXEAM-GXTWGEPZSA-N
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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

• Zearalanone

References

1. 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.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1105–. ISBN 978-3-88763-075-1.
3. 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.
4. 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.
5. Health Canada, Questions and Answers - Hormonal Growth Promoters
6. 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.
7. Lindsay DG (August 1985). "Zeranol--a 'nature-identical' oestrogen?". Food Chem Toxicol. 23 (8): 767–74. PMID 2931335.
8. 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.