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Merck
CN

SML0438

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
UNSPSC Code:
51111800
EC Number:
223-046-5
NACRES:
NA.77

Key Documents

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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 key

PTQMMNYJKCSPET-OMHQDGTGSA-N

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

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

Quality Level

100

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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).
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. 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

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
126M4730V
023M4727V

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Saunders Handbook of Veterinary Drugs: Small and Large Animal (2015)
Byung Ha Chung et al.
Cancer letters, 236(2), 222-228 (2005-07-21)
Perillyl alcohol is a hydroxylated monocyclic monoterpene. In animal study, monoterpene has shown to have an anti-tumor effect. The aim of this study is to evaluate whether POH plays an important role in the development and progression of prostate cancer
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)
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
Abdulmaged M Traish et al.
Fertility and sterility, 77 Suppl 4, S11-S18 (2002-05-15)
In women, androgens modulate the physiological function of many reproductive and sexual organs, including the ovaries, uterus, vagina, oviducts, clitoris, and mammary gland. In this article, we review the mechanisms of androgen action and discuss new data on the effects
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