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=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

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 35 Target ID: CHEMBL3401 Sources: http://www.ncbi.nlm.nih.gov/pubmed/20966043	Activator 1430	4.0 µM [EC50]
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12828470	Agonist 2678	24.0 nM [EC50]
smooth muscle contraction 13 Target ID: GO:0006939 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9147025	Inhibitor 8297	15.62 µM [IC50]
Estrogen receptor 75 Target ID: CHEMBL2093866 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9867255	Agonist 2678	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 8429	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 -3.16224E10

PubMed

Title	Date	PubMed
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture.	1999 Dec	10606005
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.	2001 May	11331656
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 Jul	15276617
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.	2010 Feb 15	19913605
miRNA-34b as a tumor suppressor in estrogen-dependent growth of breast cancer cells.	2011	22113133
Effect of zeranol on expression of apoptotic and cell cycle proteins in murine placentae.	2013 Dec 6	24120472
Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors.	2014 Oct 1	25106122
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 Feb	25349334

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 `Sat Dec 16 17:07:05 UTC 2023` Edited by `admin` on `Sat Dec 16 17:07:05 UTC 2023`
Record UNII	76LO2L2V39
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZERANOL

Official 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

RALABOL

Brand 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