4-雄烯-11β-醇-3,17-二酮

4-雄烯-11β-醇-3,17-二酮用途

11-Beta-hydroxyandrostenedione (4-Androsten-11β-ol-3,17-dione) 是一种主要存在于肾上腺的类固醇 (11β-羟化酶存在于肾上腺组织,但在卵巢组织中不存在)。11-Beta-hydroxyandrostenedione 是一种 11β-羟基类固醇脱氢酶 (11βHSD) 同工酶抑制剂。随着 4-androstenedione 的增加,测量血浆 11-Beta-hydroxyandrostenedione 可以区分高雄激素血症的肾上腺或卵巢起源。

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4-雄烯-11β-醇-3,17-二酮名称

[ CAS 号 ]:
382-44-5

[ 中文名 ]:
4-雄烯-11β-醇-3,17-二酮

[ 英文名 ]:
11-Beta-hydroxyandrostenedione

[中文别名 ]:

[英文别名 ]:

Androst-4-ene-3,17-dione, 11β-hydroxy-
U 2826
Androst-4-ene-3,17-dione, 11-hydroxy-, (11β)-
11β-hydroxyandrost-4-ene-3,17-dione
(11β)-11-Hydroxyandrost-4-ene-3,17-dione
4-Androsten-11beta-ol-3,17-dione
11beta-Hydroxyandrostenedione
11β-Hydroxy-4-androsten-3,17-dione
11beta-Hydroxyandrost-4-ene-3,17-dione
Androst-4-ene-3,17-dione-11beta-ol

4-雄烯-11β-醇-3,17-二酮生物活性

[ 描述 ]:

[ 相关类别 ]:

研究领域 >> 内分泌

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

为了确定这种转化是由CYP17A1的裂解酶活性催化的,在LNCaP细胞系中检测了21-脱氧皮质激素(21dF)和21-脱氧皮质激素(21dE)。在转染CYP17A1后,11-β-羟基雄烯二酮(11OHA4)-途径代谢物增加,21dF和21dE实际上分别被CYP17A1代谢为11-β-羟基雄烯二酮和11-酮孕酮(11KP4)[2]。

[体内研究]

21-羟化酶缺乏症、库欣综合征、肾上腺源性高雄激素血症患者血浆中11-β-羟基雄烯二酮(11-β-羟基-4-雄烯-3,17-二酮)浓度很高,先天性11-羟化酶缺乏症和肾上腺功能不全患者血浆中11-β-羟基雄烯二酮浓度很低。因此,当血浆4-雄烯二酮升高时,测量血浆11β-羟基雄烯二酮水平以确定高雄激素血症的肾上腺或卵巢起源是有用的[1]。

[参考文献]

[1]. Ibrahim F, et al. Plasma 11beta-hydroxy-4-androstene-3,17-dione: comparison of a time-resolved fluoroimmunoassay using a biotinylated tracer with a radioimmunoassay using a tritiated tracer. J Steroid Biochem Mol Biol. 2003 Apr;84(5):563-8.

[2]. Rachelle Gent, et al. 11α-Hydroxyprogesterone, a potent 11β-hydroxysteroid dehydrogenase inhibitor, is metabolised by steroid-5α-reductase and cytochrome P450 17αhydroxylase/17,20-lyase to produce C11α-derivatives of 21-deoxycortisol

4-雄烯-11β-醇-3,17-二酮物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
475.3±45.0 °C at 760 mmHg

[ 熔点 ]:
197-199℃

[ 分子式 ]:
C₁₉H₂₆O₃

[ 分子量 ]:
302.408

[ 闪点 ]:
255.4±25.2 °C

[ 精确质量 ]:
302.188202

[ PSA ]:
54.37000

[ LogP ]:
1.27

[ 蒸汽压 ]:
0.0±2.7 mmHg at 25°C

[ 折射率 ]:
1.569

[ 储存条件 ]:
室温

4-雄烯-11β-醇-3,17-二酮MSDS

详细MSDS(安全技术说明书)

4-雄烯-11β-醇-3,17-二酮安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3.0

4-雄烯-11β-醇-3,17-二酮合成路线

详细合成路线

4-雄烯-11β-醇-3,17-二酮文献

11β-Hydroxyandrostenedione, the product of androstenedione metabolism in the adrenal, is metabolized in LNCaP cells by 5α-reductase yielding 11β-hydroxy-5α-androstanedione

J. Steroid Biochem. Mol. Biol. 138 , 132-42, (2013)

• Etomidate inhibited DOC, deoxycortisol, A4 and T conversion in H295R cells. • CYP11B1 11β-hydroxylates A4 and T; CYP11B2 11β-hydroxylates T. • 11βHSD1 converts 11KA4 and 11KT; 11βHSD2 converts 11OHA...

Oxygen availability as a regulatory factor of androgen synthesis by adrenocortical cells.

Endocrinology 132(1) , 255-60, (1993)

Molecular oxygen is an obligatory substrate of all cytochrome P-450 (cyt P-450) hydroxylases involved in the steroid biosynthetic pathways. However, oxygen-derived free radicals are highly destructive...

11beta-hydroxyandrostenedione and delta5-androstenediol as markers of adrenal androgen production in patients with 21-hydroxylase-deficient nonclassic adrenal hyperplasia.

Fertil. Steril. 72(6) , 996-1000, (1999)

To determine the sensitivity of 11beta-hydroxyandrostenedione (11-OHA4) and delta5-androstenediol (ADIOL) as markers of excessive adrenal androgen production.Prospective study.Academic medical centers...

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