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SML0438

Sigma-Aldrich

Mibolerone

≥98% (HPLC)

Sinónimos:

(7α,17β)-17-Hydroxy-7,17-dimethylestr-4-en-3-one, 7α,17α-Dimethyl-19-nortestosterone

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About This Item

Fórmula empírica (notación de Hill):
C20H30O2
Número de CAS:
Peso molecular:
302.45
EC Number:
UNSPSC Code:
51111800
NACRES:
NA.77
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Quality Level

assay

≥98% (HPLC)

form

powder

drug control

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

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@H]4CCC(=O)C=C4C[C@H]3C)CC2)CC1)C)C

InChI

1S/C20H30O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h11-12,15-18,22H,4-10H2,1-3H3/t12-,15+,16-,17+,18-,19+,20+/m1/s1

InChI key

PTQMMNYJKCSPET-OMHQDGTGSA-N

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General description

The synthetic androgen mibolerone (7α,17α dimethyl-19-nortestosterone) is an androgenic steroid.[1]

Biochem/physiol Actions

Mibolerone is a synthetic anabolic steroid with a similar profile of activity as R1881 (Metribolone) with a higher affinity (Kd = 1.5 nM) for the androgen receptor in human prostate tissue than R1881 (Kd = 2.3 nM).
Mibolerone is a synthetic anabolic steroid; potent androgen receptor agonist.
The synthetic androgen mibolerone (7α,17α dimethyl-19-nortestosterone) reversibly blocks the multiplication of LNCaP (human prostate carcinoma cell line) cells.[2] In prostate, liver, and cultured cells, it serves as an efficient radioactive ligand for the quantitation and characterization of androgen receptors.[3]

pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Eugene Bratoeff et al.
The Journal of steroid biochemistry and molecular biology, 111(3-5), 275-281 (2008-07-23)
In this study, we report the synthesis and biological evaluation of several new 3-substituted pregna-4,16-diene-6,20-dione derivatives (11a-11d). These compounds were prepared from the commercially available 16-dehydropregnenolone acetate. The biological effect of these steroids was demonstrated in in vivo and in
M Bidosee et al.
International journal of andrology, 34(2), 124-137 (2010-06-16)
We previously showed that growth hormone (GH) receptors (GHR) are expressed in the most commonly studied human prostate cancer (PCa) cell lines and that GHR isoforms undergo differential, cell-type-specific hormonal regulation. We now report that human GH (hGH) can stimulate/modulate
Wayne Balkan et al.
Biochemical and biophysical research communications, 328(3), 783-789 (2005-02-08)
Despite their clinical importance for skeletal growth and homeostasis, the actions of androgens on osteoblastic cells are not well understood. MC3T3-E1 cells, a nontransformed murine preosteoblastic cell line, that traverse the stages of osteoblastic differentiation within 30 days in vitro
The use of radioactive 7α,17α?dimethyl?19?nortestosterone (mibolerone) in the assay of androgen receptors.
Schilling K and Liao S
Prostate, 5(6), 581-588 (1984)
Elisa J Cops et al.
The Journal of steroid biochemistry and molecular biology, 110(3-5), 236-243 (2008-06-03)
Androgen signaling, mediated by the androgen receptor (AR), is a critical factor influencing growth of normal and malignant breast cells. Given the increasing use of exogenous androgens in women, a better understanding of androgen action in the breast is essential.

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