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Merck
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Documentos clave

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:
3704-09-4
Peso molecular:
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

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.

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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
126M4730V
023M4727V

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R J Edmondson et al.
British journal of cancer, 86(6), 879-885 (2002-04-16)
The pathogenesis of epithelial ovarian cancer remains unclear. From epidemiological studies raised levels of androgens have been implicated to increase the risk of developing the disease. The purpose of this study was to determine the responses of normal human ovarian
Linda Munson
Theriogenology, 66(1), 126-134 (2006-04-22)
Contraceptives are used for reversible reproductive control in genetically valuable wild felids, as permanent reproductive control in generic wild felids, and as an economically practicable means to control feral cats. The progestin contraceptives, megestrol acetate, melengesterol acetate, medroxyprogesterone acetate, and
Erik J Tokar et al.
Differentiation; research in biological diversity, 73(9-10), 463-473 (2005-12-15)
Theories of cell lineage in human prostatic epithelium, based on protein expression, propose that basal and luminal cells: 1) are either independently capable of self-renewal or 2) arise from stem cells expressing a full spectrum of proteins (p63, cytokeratins CK5/14
Transcriptional down-regulation of c-myc in human prostate carcinoma cells by the synthetic androgen mibolerone.
Wolf DA, et al.
British Journal of Cancer, 65(3), 376?382-376?382 (1992)
Shereen A Ghali et al.
The Journal of clinical endocrinology and metabolism, 88(5), 2185-2193 (2003-05-03)
Five mutations in the ligand-binding domain (LBD) of the human androgen receptor (hAR) found in patients with varying degrees of androgen insensitivity syndrome (AIS) were investigated for their effects on receptor dynamics. These were Arg(871)Gly (mild), Ser(814)Asn (partial), Glu(772)Ala (partial)
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