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P7754

Sigma-Aldrich

5α-Pregnan-3,20-dion (Allo)

progesterone metabolite

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C21H32O2
CAS-Nummer:
566-65-4
Molekulargewicht:
316.48
EG-Nummer:
209-297-3
MDL-Nummer:
MFCD00067132
UNSPSC-Code:
51111800
PubChem Substanz-ID:
24898872
NACRES:
NA.77

Qualitätsniveau

200

Form

powder

SMILES String

[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

InChIKey

XMRPGKVKISIQBV-BJMCWZGWSA-N

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Acetylaceton for synthesis

Sigma-Aldrich

8.00023

Acetylaceton

Pregnenolone Avanti Research™ - A Croda Brand

Avanti

700142P

Pregnenolone

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
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.
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
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
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
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