ZERANOL

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 Search

SMILES

C[C@H]1CCC[C@H](O)CCCCCC2=CC(O)=CC(O)=C2C(=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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.fda.gov/ohrms/dockets/98fr/05-038-233-fois001.pdf
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/6351181 and http://www.ncbi.nlm.nih.gov/pubmed/20002219

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 Target	Pharmacology	Potency
Pregnane X receptor 36 Target ID: CHEMBL3401 Sources: http://www.ncbi.nlm.nih.gov/pubmed/20966043	Activator 1447	4.0 µM [EC50]
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12828470	Agonist 2752	24.0 nM [EC50]
smooth muscle contraction 13 Target ID: GO:0006939 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9147025	Inhibitor 8504	15.62 µM [IC50]
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9867255	Agonist 2752	1.8 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Low weight in beef cattle 1 Sources: http://www.fda.gov/ohrms/dockets/98fr/05-038-233-fois001.pdf	Primary		Approved 8583	RALGRO Approved Use For increased weight gain and for improved feed conversion of weaned beef calves, growing beef cattle, feedlot steers and feedlot heifers. For increased rate of weight gain of suckling beef calves. Launch Date 1968

C_max

Value	Dose	Co-administered	Analyte	Population
0.32 μg × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6624136/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		ZERANOL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6624136/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		ZERANOL blood	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein.	2015-02	25349334
Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors.	2014-10-01	25106122
Effect of zeranol on expression of apoptotic and cell cycle proteins in murine placentae.	2013-12-06	24120472
Zeranol upregulates corticotropin releasing hormone expression in the placental cell line JEG-3.	2013-06-07	23538034
Selective activation of zebrafish estrogen receptor subtypes by chemicals by using stable reporter gene assay developed in a zebrafish liver cell line.	2012-02	22045033
miRNA-34b as a tumor suppressor in estrogen-dependent growth of breast cancer cells.	2011	22113133
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.	2010-02-15	19913605
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Phytoestrogen alpha-zearalanol antagonizes homocysteine-induced imbalance of nitric oxide/endothelin-1 and apoptosis in human umbilical vein endothelial cells.	2006	16757814
Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types.	2004-07	15276617
The immune system of geriatric mice is modulated by estrogenic endocrine disruptors (diethylstilbestrol, alpha-zearalanol, and genistein): effects on interferon-gamma.	2003-12-15	14636701
Oestrogenic potencies of Zeranol, oestradiol, diethylstilboestrol, Bisphenol-A and genistein: implications for exposure assessment of potential endocrine disrupters.	2001-05	11331657
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.	2001-05	11331656
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.	2000-05	10811566
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture.	1999-12	10606005

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 Created by `admin` on `Wed Apr 02 08:45:24 GMT 2025` Edited by `admin` on `Wed Apr 02 08:45:24 GMT 2025`
Record UNII	76LO2L2V39
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZERANOL

Official Name

English

RALABOL

Preferred Name

English

THFES (HM)

Code

English

P-1496

Code

English

ZERANOL [USAN]

Common Name

English

ZERANOL [MART.]

Common Name

English

(-)-.ALPHA.-ZEARALANOL

Common Name

English

zeranol [INN]

Common Name

English

ZERANOL [GREEN BOOK]

Common Name

English

RALGRO

Brand Name

English

ZERANOL [MI]

Common Name

English

MK-188

Code

English

1H-2-BENZOXACYCLOTETRADECIN-1-ONE, 3,4,5,6,7,8,9,10,11,12-DECAHYDRO-7,14,16-TRIHYDROXY-3-METHYL-, (3S,7R)-

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 556.760