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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H26O5
Molecular Weight 322.396
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZERANOL

SMILES

C[C@H]1CCC[C@H](O)CCCCCC2=C(C(O)=CC(O)=C2)C(=O)O1

InChI

InChIKey=DWTTZBARDOXEAM-GXTWGEPZSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H26O5
Molecular Weight 322.396
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Zeranol is a non-steroidal anabolic growth promoter with potent estrogenic activity that is widely used as a growth promoter in the US beef industry. It is a mycotoxin, derived from fungi in the Fusarium family, it is an estrogen agonist. Zeranol is approved for use as a growth promoter in livestock, including beef cattle, in the United States. In Canada, it is approved for use in beef cattle only. Zeranol was officially banned in Europe due to safety concerns because of its potential carcinogenic and endocrine-disrupting biological activity. Merck Animal Health markets zeranol under the brand name Ralgro. It has being shown, that zeranol may increase cancer cell proliferation in already existing breast cancer.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.0 µM [EC50]
24.0 nM [EC50]
15.62 µM [IC50]
1.8 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RALGRO

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
RALGRO (Zeranol): Beef cattle: One implant containing 36 mg zeranol. Feedlot lambs: One implant containing 12 mg. zeranol
Route of Administration: Transdermal
In Vitro Use Guide
Zeranol (2‑50 nM) was able to significantly promote cell proliferation, aromatase mRNA expression, aromatase activity and estrogen production in primary cultured human breast preadipocytes
Substance Class Chemical
Record UNII
76LO2L2V39
Record Status Validated (UNII)
Record Version