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.^[1][2][3]

Trade namesFrideron, Ralabol, Ralgro, Ralone, Zerano

Other namesZearanol; α-Zearalanol; Zearalanol; MK-188; P-1496

Routes of
administrationBy mouth

Drug classNonsteroidal estrogen

Quick facts Clinical data, Trade names ...

Zeranol

Clinical data
Trade names	Frideron, Ralabol, Ralgro, Ralone, Zerano
Other names	Zearanol; α-Zearalanol; Zearalanol; MK-188; P-1496
Routes of administration	By mouth
Drug class	Nonsteroidal estrogen
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
CAS Number	26538-44-3 N
PubChem CID	2999413
ChemSpider	2271133 N
UNII	76LO2L2V39
ChEMBL	ChEMBL371463 Y
CompTox Dashboard (EPA)	DTXSID4022315
ECHA InfoCard	100.043.411
Chemical and physical data
Formula	C18H26O5
Molar mass	322.401 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@H]1CCC[C@H](O)CCCCCc2cc(O)cc(O)c2C(=O)O1
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 N Key:DWTTZBARDOXEAM-GXTWGEPZSA-N N
NY (what is this?)  (verify)

Close

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] It is a metabolite of zearalenone.^[9]