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R0908

Sigma-Aldrich

R1881

≥98% (HPLC), Androgen receptor agonist, powder

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

Key Documents

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Product Name

R1881, ≥98% (HPLC)

Quality Level

100

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.
R1881 (methyltrienolone) is a potent synthetic androgen.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
027M4704V
126M4609V
076M4713V
085M4610V
055M4614V

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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
Annelies Van Hemelryk et al.
Biomolecules, 11(11) (2021-11-28)
Organoid-based studies have revolutionized in vitro preclinical research and hold great promise for the cancer research field, including prostate cancer (PCa). However, experimental variability in organoid drug testing complicates reproducibility. For example, we observed PCa organoids to be less affected
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
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
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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