3728 Zeranol Zeranol is isolated from Fusarium species. It is an anabolic agent and estrogenic agent (mainly veterinary use). Zeranol is used as a growth promoter for food animals. It was banned by the EU in 1989, but is still permitted in the USA and some other countries. It may also arise in livestock by ingestion of Fusarium contaminated pasture or feeds. Zeranol has been shown to exhibit muscle building function (A7851). Zeranol belongs to the family of Macrolides and Analogues. These are organic compounds containing a lactone ring of at least twelve members[1]. The term 'macrolide' encompasses a diverse family of unrelated compounds with large macrolactam rings[2]. 26538-44-3 22283 C18H26O5 White powder. 182 - 184°C Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Zeranol acts as an agonist at the estrogen receptors, interfering with the binding of natural estrogens. This disrupts hormone levels and affects a number of signaling processes, leading to various reproductive disorders in males and females. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (A2965, A2961, A3014) Metabolism of zeranol occurs in the liver. During phase I metabolism, dehydrogenation produces zearalanone as the major metabolite and beta-zearalanol as the minor metabolite. Cytochrome P450 enzymes also catalyze the aromatic hydroxylation of zeranol, producing 13-hydroxy-alpha-zearalanol and 15-hydroxy-alpha-zearalanol. During phase II metabolism reduction/oxidation occurs, forming the glucuronide and sulfate conjugates of zearalanone and beta-zearalanol. In humans, the metabolites are excreted mainly in the urine. (A2966) Not listed by IARC. Zeranol is a mycotoxin derived from fungi in the Fusarium family, and may be found as a contaminant in fungus-infected crops. (L1954) Estimated acceptable daily intake is 0 - 0.5 ug/kg. (L1955) Zeranol is an estrogen-like endocrine disrupting chemical that interferes with the binding of natural estrogens, disrupting hormone levels and causing various reproductive disorders in males and females. It has been shown to cause developmental problems in animals by causing tissue malformations and produce irregularities in the estrous cycle. In humans, zeranol induces breast cancer cell growth. (A2965) 2010-04-15T18:58:24Z 2026-05-14T19:10:00Z http://en.wikipedia.org/wiki/Zeranol C14752 DB11478 true CC1CCCC(O)CCCCCC2=CC(O)=CC(O)=C2C(=O)O1 C18H26O5 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 DWTTZBARDOXEAM-UHFFFAOYSA-N 322.396 322.178023942 Exogenous Solid 4.45 HMDB32702 20916 CHEM002644 DTXSID4022315 (3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one 86.99 88.25099999999999 35.52464030055078 0 4 3 8.677321911758112 -1.2748463853225807 0 2 3.23 -3.29 1.64e-01 g/l