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Key Documents

SML0438

Sigma-Aldrich

Mibolerone

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
3704-09-4
Molecular Weight:
302.45
EC Number:
223-046-5
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

100

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

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.

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).
The synthetic androgen mibolerone (7α,17α dimethyl-19-nortestosterone) reversibly blocks the multiplication of LNCaP (human prostate carcinoma cell line) cells. In prostate, liver, and cultured cells, it serves as an efficient radioactive ligand for the quantitation and characterization of androgen receptors.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360

Hazard Classifications

Repr. 1B

Storage Class Code

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

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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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)
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
Saunders Handbook of Veterinary Drugs: Small and Large Animal (2015)
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
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
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