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P7754

Sigma-Aldrich

5α-Pregnane-3,20-dione (allo)

progesterone metabolite

Sinonimo/i:

5α-Dihydroprogesterone, Allopregnane-3,20-dione

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About This Item

Formula empirica (notazione di Hill):
C21H32O2
Numero CAS:
566-65-4
Peso molecolare:
316.48
Numero CE:
209-297-3
Numero MDL:
MFCD00067132
Codice UNSPSC:
51111800
ID PubChem:
24898872
NACRES:
NA.77

Forma fisica

powder

Stringa SMILE

[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2

InChI

1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
XMRPGKVKISIQBV-BJMCWZGWSA-N

Azioni biochim/fisiol

A high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Pregnenolone solution 100 μg/mL in acetonitrile, certified reference material, Cerilliant®

Supelco

P-104

Pregnenolone solution

Acetilacetone for synthesis

Sigma-Aldrich

8.00023

Acetilacetone

Pregnenolone Avanti Research™ - A Croda Brand

Avanti

700142P

Pregnenolone

Cheryl A Frye et al.
Physiology & behavior, 100(3), 264-267 (2010-03-20)
Autism spectrum disorders (ASD) are a constellation of neurodevelopmental disorders associated with disruptions in social, cognitive, and/or motor behaviors. ASD are more prevalent among males than females and characterized by aberrant social and language development, and a dysregulation in stress-responding.
B E Pearson Murphy et al.
The Journal of clinical endocrinology and metabolism, 86(12), 5981-5987 (2001-12-12)
Progesterone and its 5 alpha reduced metabolite, 5 alpha-dihydroprogesterone, rise greatly in pregnancy. Both are known to have anesthetic properties, as do a number of other ring A-reduced progesterone metabolites. The possible significance of these steroids with respect to the
Ann M Rasmusson et al.
Biological psychiatry, 60(7), 704-713 (2006-08-29)
Alterations in the gamma-amino-butyric acid (GABA) neurotransmitter system have been identified in some populations with posttraumatic stress disorder (PTSD). To further investigate factors of relevance to GABAergic neurotransmission in PTSD, we measured cerebrospinal fluid (CSF) levels of allopregnanolone and pregnanolone
S Chantilis et al.
The Journal of clinical endocrinology and metabolism, 81(10), 3644-3649 (1996-10-01)
The metabolism of 5 alpha-dihydroprogesterone (5 alpha-DHP) in women and men was evaluated by defining the pattern and identity of selected metabolites excreted in urine after the iv infusion of radiolabeled 5 alpha-DHP. Virtually all of the radioactivity in urine
Penelope M Sheehan
The Australian & New Zealand journal of obstetrics & gynaecology, 46(2), 159-163 (2006-04-28)
There has been a recent resurgence of interest in the role of progesterone in the maintenance of human pregnancy and the onset of labour, following recent reports of its use to prevent preterm labour in high-risk patients. One possible mechanism
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