METRIBOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24O2
Molecular Weight	284.3927
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@]12C

InChI

InChIKey=CCCIJQPRIXGQOE-XWSJACJDSA-N

InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H24O2
Molecular Weight	284.3927
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5955468 | https://www.ncbi.nlm.nih.gov/pubmed/6605855

Metribolone, also known as methyltrienolone, an anabolic agent, binds to the androgen receptor and was studied for the treatment of advanced breast cancer. However, because of the liver toxicity, further development of this drug was discontinued. Now, this compound is used for research purpose as synthetic androgen.

Approval Year

PubMed

Title	Date	PubMed
The Flame-Retardant Tris(1,3-dichloro-2-propyl) Phosphate Represses Androgen Signaling in Human Prostate Cancer Cell Lines.	2016-05	26709203
Low dose evaluation of the antiandrogen flutamide following a Mode of Action approach.	2015-12-15	26485406
LncRNA HOTAIR Enhances the Androgen-Receptor-Mediated Transcriptional Program and Drives Castration-Resistant Prostate Cancer.	2015-10-06	26411689
p,p'-Dichlorodiphenyltrichloroethane (p,p'-DDT) and p,p'-dichlorodiphenyldichloroethylene (p,p'-DDE) repress prostate specific antigen levels in human prostate cancer cell lines.	2015-03-25	25682698
Copper signaling axis as a target for prostate cancer therapeutics.	2014-10-15	25320179
Currently used pesticides and their mixtures affect the function of sex hormone receptors and aromatase enzyme activity.	2013-10-15	23871939
Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity.	2013-10-01	24004914
Metallothionein 3: an androgen-upregulated gene enhances cell invasion and tumorigenesis of prostate carcinoma cells.	2013-10	23794209
Bisphenol A affects androgen receptor function via multiple mechanisms.	2013-05-25	23562765
Ligand-independent androgen receptor antagonism caused by the newly developed pesticide pyrifluquinazon (PFQ).	2013-01	23146716
Androgen receptor promotes ligand-independent prostate cancer progression through c-Myc upregulation.	2013	23704919
Anti-androgen effects of cypermethrin on the amino- and carboxyl-terminal interaction of the androgen receptor.	2012-02-26	22172556
Inactivation of ATM/ATR DNA damage checkpoint promotes androgen induced chromosomal instability in prostate epithelial cells.	2012	23272087
The DEK oncogene is a target of steroid hormone receptor signaling in breast cancer.	2012	23071688
Biological properties of androgen receptor pure antagonist for treatment of castration-resistant prostate cancer: optimization from lead compound to CH5137291.	2011-09	21308717
Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1.	2011-06-15	21440447
Testosterone augments polyphenol-induced DNA damage response in prostate cancer cell line, LNCaP.	2011-02	21134073
Androgen-regulated expression of arginase 1, arginase 2 and interleukin-8 in human prostate cancer.	2010-08-11	20711410
Identification of the GATA factor TRPS1 as a repressor of the osteocalcin promoter.	2009-11-13	19759027
Sex hormones, acting on the TERT gene, increase telomerase activity in human primary hematopoietic cells.	2009-09-10	19561322
Cumulative and antagonistic effects of a mixture of the antiandrogens vinclozolin and iprodione in the pubertal male rat.	2009-09	19564212
Transcriptional repression and inhibition of nuclear translocation of androgen receptor by diallyl trisulfide in human prostate cancer cells.	2009-08-01	19622577
Genome-wide impact of androgen receptor trapped clone-27 loss on androgen-regulated transcription in prostate cancer cells.	2009-04-01	19318562
Inhibition of androgen receptor transcriptional activity as a novel mechanism of action of arsenic.	2009-03	19131511
A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice.	2008-10-15	18922931
Effects of manganese superoxide dismutase silencing on androgen receptor function and gene regulation: implications for castration-resistant prostate cancer.	2008-10-01	18829485
Differential effects of resveratrol on androgen-responsive LNCaP human prostate cancer cells in vitro and in vivo.	2008-10	18586690
Curcumin blocks the activation of androgen and interlukin-6 on prostate-specific antigen expression in human prostatic carcinoma cells.	2008-08-05	18676361
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Parathyroid hormone-related protein varies with sex and androgen status in nonsmall cell lung cancer.	2007-09-15	17676588
Androgen-dependent regulation of medium and long chain fatty acids uptake in prostate cancer.	2007-09-01	17626249
The role of androgen in determining differentiation and regulation of androgen receptor expression in the human prostatic epithelium transient amplifying population.	2007-09	17541959
Squalene synthase, a determinant of Raft-associated cholesterol and modulator of cancer cell proliferation.	2007-06-29	17483544
Labeling and identification of LNCaP cell surface proteins: a pilot study.	2007-06-15	17440980
Androgen regulation of aldehyde dehydrogenase 1A3 (ALDH1A3) in the androgen-responsive human prostate cancer cell line LNCaP.	2007-06	17526768
Testosterone activates mitogen-activated protein kinase via Src kinase and the epidermal growth factor receptor in sertoli cells.	2007-05	17272394
Beta-2-microglobulin is an androgen-regulated secreted protein elevated in serum of patients with advanced prostate cancer.	2007-04-01	17404077
Proteomics analysis of the interactome of N-myc downstream regulated gene 1 and its interactions with the androgen response program in prostate cancer cells.	2007-04	17220478
Rapid, non-destructive, cell-based screening assays for agents that modulate growth, death, and androgen receptor activation in prostate cancer cells.	2007-03-01	17219378
Curcumin downregulates homeobox gene NKX3.1 in prostate cancer cell LNCaP.	2007-03	17303007
Ligand-specific dynamics of the androgen receptor at its response element in living cells.	2007-03	17189428
17beta-Estradiol differentially regulates androgen-responsive genes through estrogen receptor-beta- and extracellular-signal regulated kinase-dependent pathways in LNCaP human prostate cancer cells.	2007-02	17131305
The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor.	2007-02	17105867
Differential regulation of clusterin and its isoforms by androgens in prostate cells.	2007-01-26	17148459
Androgen induces adaptation to oxidative stress in prostate cancer: implications for treatment with radiation therapy.	2007-01	17325745
Evaluation of an in vitro model of androgen ablation and identification of the androgen responsive proteome in LNCaP cells.	2007-01	17152098
Testosterone and progesterone rapidly attenuate plasma membrane Gbetagamma-mediated signaling in Xenopus laevis oocytes by signaling through classical steroid receptors.	2007-01	17021048
p53 overexpression represses androgen-mediated induction of NKX3.1 in a prostate cancer cell line.	2006-12-31	17202838
Gene expression signature-based chemical genomic prediction identifies a novel class of HSP90 pathway modulators.	2006-10	17010675
Topographic recognition of cyclic hydrocarbons and related compounds by receptors for androgens, estrogens, and glucocorticoids.	1987	3695475

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:31:46 GMT 2025` Edited by `admin` on `Wed Apr 02 08:31:46 GMT 2025`
Record UNII	2C323EGI97
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METRIBOLONE

Official Name

English

METHYLTRIENOLONE

Preferred Name

English

NSC-92858

Code

English

Metribolone [WHO-DD]

Common Name

English

R 1881

Code

English

METRIBOLONE [MART.]

Common Name

English

metribolone [INN]

Common Name

English

17.BETA.-HYDROXY-17-METHYLESTRA-4,9,11-TRIEN-3-ONE

Systematic Name

English

METHYLTRIENOLONE [MI]

Common Name

English

R-1881

Code

English

Classification Tree Code System Code

DEA NO.

4000