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P7754

Sigma-Aldrich

5α-Pregnane-3,20-dione (allo)

progesterone metabolite

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C21H32O2
Número de CAS:
566-65-4
Peso molecular:
316.48
Número CE:
209-297-3
Número MDL:
MFCD00067132
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
24898872
NACRES:
NA.77

Nivel de calidad

200

Formulario

powder

cadena SMILES

[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

Clave InChI

XMRPGKVKISIQBV-BJMCWZGWSA-N

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000355145
0000355145
SLCQ9503
SLCP1584
SLCJ1879

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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
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
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.
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