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R0908

Sigma-Aldrich

R1881

≥98% (HPLC)

Synonym(s):

(17b)-17-Hydroxy-17-methyl-Estra-4,9,11-trien-3-one, Methyltrienolone, Metribolone, NSC 92858, RU 1881

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About This Item

Empirical Formula (Hill Notation):
C19H24O2
CAS Number:
965-93-5
Molecular Weight:
284.39
MDL number:
MFCD00199021
UNSPSC Code:
51111800
PubChem Substance ID:
329823993
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -48 to -68°

drug control

USDEA Schedule IIIN; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

color

light yellow to yellow

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

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

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

InChI key

CCCIJQPRIXGQOE-XWSJACJDSA-N

Biochem/physiol Actions

Androgen receptors (ARs) are nuclear hormone receptors/transcription factors. R1881, also known as methyltrienolone, is a synthetic androgen. It is the gold standard AR agonist.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Juliet Richards et al.
Cancer research, 72(9), 2176-2182 (2012-03-14)
Prostate cancer progression can be associated with androgen receptor (AR) mutations acquired following treatment with castration and/or an antiandrogen. Abiraterone, a rationally designed inhibitor of CYP17A1 recently approved for the treatment of docetaxel-treated castration-resistant prostate cancer (CRPC), is often effective
Nader Al Nakouzi et al.
European urology, 68(2), 228-235 (2014-05-20)
Cabazitaxel, abiraterone acetate (AA), and enzalutamide have been approved for the treatment of patients with metastatic castration-resistant prostate cancer (mCRPC) following docetaxel chemotherapy. Whether taxanes and next-generation androgen receptor (AR) axis inhibitors are cross-resistant or not is a subject of
Liyuan Yin et al.
Scientific reports, 10(1), 1216-1216 (2020-01-29)
Advanced and therapy-resistant prostate tumors often display neural or neuroendocrine behavior. We assessed the consequences of prostate cancer cell interaction with neural cells, which are rich in the human prostate and resident of the prostate tumor. In 3-dimensional co-culture with
Robert S Hudson et al.
Molecular cancer, 12, 13-13 (2013-02-16)
Ultraconserved regions (UCR) are genomic segments of more than 200 base pairs that are evolutionarily conserved among mammalian species. They are thought to have functions as transcriptional enhancers and regulators of alternative splicing. Recently, it was shown that numerous RNAs
Lingyan Jin et al.
Cancer research, 77(20), 5564-5575 (2017-08-19)
Resistance invariably develops to antiandrogen therapies used to treat newly diagnosed prostate cancers, but effective treatments for castration-resistant disease remain elusive. Here, we report that the transcriptional coactivator CBP/p300 is required to maintain the growth of castration-resistant prostate cancer. To
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