Zeranol

Zeranol (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip 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.

Zeranol
Clinical data
Trade namesFrideron, Ralabol, Ralgro, Ralone, Zerano
Other namesZearanol; α-Zearalanol; Zearalanol; MK-188; P-1496
Routes of
administration		By mouth
Drug classNonsteroidal estrogen
Identifiers
  • (3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.411
Chemical and physical data
FormulaC18H26O5
Molar mass322.401 g·mol−1
3D model (JSmol)
  • C[C@H]1CCC[C@H](O)CCCCCc2cc(O)cc(O)c2C(=O)O1
  • 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 N
  • Key:DWTTZBARDOXEAM-GXTWGEPZSA-N N
 NY (what is this?)  (verify)

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. In Canada, it is approved for use in beef cattle only. 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, dietary exposure from the use of zeranol-containing implants in cattle is insignificant. 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. It is a metabolite of zearalenone.

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