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

[H][C@@]12CC[C@](C)(O)[C@@]1(C)C=CC3=C4CCC(=O)C=C4CC[C@@]23[H]

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

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
Topographic recognition of cyclic hydrocarbons and related compounds by receptors for androgens, estrogens, and glucocorticoids.	1987	3695475
Inhibition of androgen receptor signaling by selenite and methylseleninic acid in prostate cancer cells: two distinct mechanisms of action.	2006 Aug	16928829
p53 overexpression represses androgen-mediated induction of NKX3.1 in a prostate cancer cell line.	2006 Dec 31	17202838
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 Apr	17220478
Beta-2-microglobulin is an androgen-regulated secreted protein elevated in serum of patients with advanced prostate cancer.	2007 Apr 1	17404077
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 Feb	17131305
The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor.	2007 Feb	17105867
Androgen induces adaptation to oxidative stress in prostate cancer: implications for treatment with radiation therapy.	2007 Jan	17325745
Evaluation of an in vitro model of androgen ablation and identification of the androgen responsive proteome in LNCaP cells.	2007 Jan	17152098
Testosterone and progesterone rapidly attenuate plasma membrane Gbetagamma-mediated signaling in Xenopus laevis oocytes by signaling through classical steroid receptors.	2007 Jan	17021048
Differential regulation of clusterin and its isoforms by androgens in prostate cells.	2007 Jan 26	17148459
Androgen regulation of aldehyde dehydrogenase 1A3 (ALDH1A3) in the androgen-responsive human prostate cancer cell line LNCaP.	2007 Jun	17526768
Labeling and identification of LNCaP cell surface proteins: a pilot study.	2007 Jun 15	17440980
Squalene synthase, a determinant of Raft-associated cholesterol and modulator of cancer cell proliferation.	2007 Jun 29	17483544
Curcumin downregulates homeobox gene NKX3.1 in prostate cancer cell LNCaP.	2007 Mar	17303007
Ligand-specific dynamics of the androgen receptor at its response element in living cells.	2007 Mar	17189428
Rapid, non-destructive, cell-based screening assays for agents that modulate growth, death, and androgen receptor activation in prostate cancer cells.	2007 Mar 1	17219378
Testosterone activates mitogen-activated protein kinase via Src kinase and the epidermal growth factor receptor in sertoli cells.	2007 May	17272394
The role of androgen in determining differentiation and regulation of androgen receptor expression in the human prostatic epithelium transient amplifying population.	2007 Sep	17541959
Androgen-dependent regulation of medium and long chain fatty acids uptake in prostate cancer.	2007 Sep 1	17626249
Parathyroid hormone-related protein varies with sex and androgen status in nonsmall cell lung cancer.	2007 Sep 15	17676588
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Curcumin blocks the activation of androgen and interlukin-6 on prostate-specific antigen expression in human prostatic carcinoma cells.	2008 Nov-Dec	18676361
Differential effects of resveratrol on androgen-responsive LNCaP human prostate cancer cells in vitro and in vivo.	2008 Oct	18586690
Effects of manganese superoxide dismutase silencing on androgen receptor function and gene regulation: implications for castration-resistant prostate cancer.	2008 Oct 1	18829485
A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice.	2008 Oct 15	18922931
Genome-wide impact of androgen receptor trapped clone-27 loss on androgen-regulated transcription in prostate cancer cells.	2009 Apr 1	19318562
Transcriptional repression and inhibition of nuclear translocation of androgen receptor by diallyl trisulfide in human prostate cancer cells.	2009 Aug 1	19622577
Inhibition of androgen receptor transcriptional activity as a novel mechanism of action of arsenic.	2009 Mar	19131511
Identification of the GATA factor TRPS1 as a repressor of the osteocalcin promoter.	2009 Nov 13	19759027
Cumulative and antagonistic effects of a mixture of the antiandrogens vinclozolin and iprodione in the pubertal male rat.	2009 Sep	19564212
Sex hormones, acting on the TERT gene, increase telomerase activity in human primary hematopoietic cells.	2009 Sep 10	19561322
Androgen-regulated expression of arginase 1, arginase 2 and interleukin-8 in human prostate cancer.	2010 Aug 11	20711410
Testosterone augments polyphenol-induced DNA damage response in prostate cancer cell line, LNCaP.	2011 Feb	21134073
Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1.	2011 Jun 15	21440447
Biological properties of androgen receptor pure antagonist for treatment of castration-resistant prostate cancer: optimization from lead compound to CH5137291.	2011 Sep	21308717
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
Anti-androgen effects of cypermethrin on the amino- and carboxyl-terminal interaction of the androgen receptor.	2012 Feb 26	22172556
Androgen receptor promotes ligand-independent prostate cancer progression through c-Myc upregulation.	2013	23704919
Ligand-independent androgen receptor antagonism caused by the newly developed pesticide pyrifluquinazon (PFQ).	2013 Jan	23146716
Bisphenol A affects androgen receptor function via multiple mechanisms.	2013 May 25	23562765
Metallothionein 3: an androgen-upregulated gene enhances cell invasion and tumorigenesis of prostate carcinoma cells.	2013 Oct	23794209
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 Oct 1	24004914
Currently used pesticides and their mixtures affect the function of sex hormone receptors and aromatase enzyme activity.	2013 Oct 15	23871939
Copper signaling axis as a target for prostate cancer therapeutics.	2014 Oct 15	25320179
Low dose evaluation of the antiandrogen flutamide following a Mode of Action approach.	2015 Dec 15	26485406
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 Mar 25	25682698
LncRNA HOTAIR Enhances the Androgen-Receptor-Mediated Transcriptional Program and Drives Castration-Resistant Prostate Cancer.	2015 Oct 6	26411689
The Flame-Retardant Tris(1,3-dichloro-2-propyl) Phosphate Represses Androgen Signaling in Human Prostate Cancer Cell Lines.	2016 May	26709203

Name

Type

Language

METRIBOLONE

Official 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

METHYLTRIENOLONE

Common Name

English

R-1881

Code

English

Classification Tree Code System Code

DEA NO.

4000